32 Luxury Rentals In Florida Keys, Florida

Roohi
Contributing Writer
Updated
| 13 min read

The Florida Keys are a stretch of tropical islands located off the southern coast of Florida. It is a coral cay archipelago that forms the southernmost portion of the United States. This place is known for tons of recreational activities such as fishing, boating, snorkeling, and scuba diving. It is a great place to spend a quick and relaxing getaway with friends and family. The picturesque landscapes coupled with the exotic climate make this place a major crowd-puller during the holiday season. Take a look at some of the most value-for-money and luxurious vacation rentals in Florida Keys, Florida.

What to look forward to:

  • The USA's first undersea park, John Pennekamp Coral Reef State Park can be explored in many ways, whether you prefer to watch from a glass boat or swim with the fish in their coral reefs while diving or snorkeling. It's also possible to spend some quiet time fishing in designated areas.
  • Whether you plan to shop, eat, or dance your way through Key West, Mallory Square is the place to be. It is home to some of the island city's best restaurants, shops, museums, and live entertainment opportunities, ensuring no moment is boring.

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to luxury services and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 26, 2025.

1. Spacious rental with a boat dock facility; Key Colony Beach (from USD 8943)

Best for: Group trips, watersports enthusiasts

Whether you want to enjoy a fun-filled weekend with your family or friends or a romantic evening with someone special, the exquisite setting of this mansion rental offers everything you could possibly want! Enjoy boating with easy access to a dock or relax in the charming private pool area, which is beautifully lit at night.

Facing the pool, there is also an alfresco kitchen with a barbecue setup and classy seating arrangements. There’s a private hot tub where you may unwind after enjoying an energetic game of tennis.

Key Colony Beach, Florida, United States

142.32 km (88.5 mi) from Miami Seaquarium
9 reviews   Wifi Available
ENTIRE HOME 6 Beds 12 Guests 5 Bedrooms 6 Bathrooms

Accommodates: 12

Top guest reviews
Location:
the house is amazingly beautiful the location and neighborhood is perfect
Read more reviews

2. Coco’s Ocean Front Paradise; Key Largo (from USD 1300)

Best for: Watersports enthusiasts, group stays

Coco’s Ocean Front Paradise makes it possible for guests to enjoy the beauty of Florida Keys without having to share the experience with strangers. Located next to this property is a private beach and 300.0 feet (91.4 meters) of oceanfront dock. Laze around at the beach if you so choose or take the kayak available here out for a spin to explore more of the area. When you’re done having fun outdoors, you can head back inside this Airbnb property and shoot some pool or play ping pong with your loved ones.

This property is also perfectly capable of accommodating large parties. Guests have five bedrooms to choose from, with three of them featuring queen-size beds and the other offering a king-size bed.

Key Largo, Florida, United States

81.28 km (50.5 mi) from Miami Seaquarium
18 reviews   Wifi Available
ENTIRE HOME 5 Beds 10 Guests 5 Bedrooms 6 Bathrooms

Accommodates: 10

Top guest reviews
Host:
host was very responsive to questions
alfredo is a great host
good rental felt that owner was very authoritative
alfredo is an excellent host very responsive when our group had questions
alfredo was very responsive and answered any questions i had
Location:
the location is beautiful and relaxing
it’s a great location but not really a beach
great location for exploring the keys
Cleanliness:
spectacularly clean as well
Amenities & Room:
the furnishings are comfortable and there is plenty of outdoor seating to enjoy the water views
beautiful house with awesome views our 2 families had a great trip with plenty of room
great views from every room very nice house to bring your boat
this house is huge and it has 2 full kitchens
Read more reviews

3. Opulent estate with varied outdoor amenities; Marathon (from USD 14167)

Best for: Outdoor enthusiasts, group stays, watersports enthusiasts

Experience what it’s like to live in the lap of luxury by booking this Airbnb property. This property spreads across 1.7 acres (0.7 hectares) of prime Florida real estate and it even comes with a private lagoon. The private lagoon with the dock is just one of the many outdoor attractions this property has to offer. During your stay, you can also play some games on the private tennis court or take the paddle boards and kayaks out for a short ride using the provided dock.

Inside, you’ll find a fully equipped kitchen complete with three types of coffee makers, so you can enjoy your brew the way you like it. Furthermore, you don’t have to miss out on your favorite shows while staying here. The 75-inch HDTV comes with access to Apple TV, Disney+, Hulu, and premium cable channels.

Marathon, Florida, United States

133.67 km (83.1 mi) from Miami Seaquarium
36 reviews   Wifi Available
ENTIRE HOME 6 Beds 10 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 10

Top guest reviews
Host:
great caretaker who made sure everything was smooth
the owners were very responsive and helpful with restaurant suggestions and questions
it's easy to see that the owner takes great pride in keeping this home in excellent condition
Location:
that and the incredible location were the crown jewels not to mention the amazing sunset
Cleanliness:
the pool was well heated and the house was clean inside and out
Amenities & Room:
we loved cooking on the pristine grill the kitchen has 3 ovens all immaculate
Read more reviews

4. Pink Beach Paradise; Sugarloaf Key (from USD 24728)

Best for: Beach lovers, group trips, watersports enthusiasts

Pink Beach Paradise is an apt name for this Airbnb property considering its idyllic features and surroundings. The main attraction of the property is undoubtedly the access it offers to a private beach. If you’ve always wanted to explore the waters of Florida Keys at your leisure, then this beach home will suit you well with its offering of dock and kayaks.

On days when your body could use a bit of extra pampering, you can take a dip in the hot tub lined with travertine tiles. Relax further by walking through the front gardens and basking in their calming atmosphere.

Furthermore, space won’t be an issue if you decide to book this beach house. It comes with five bedrooms and is capable of accommodating more than 16 guests.

Upper Sugarloaf Key, Florida, United States

185.63 km (115.4 mi) from Miami Seaquarium
25 reviews   Wifi Available
ENTIRE HOME 10 Beds 16 Guests 5 Bedrooms 2 Bathrooms

Accommodates: 16

Top guest reviews
Host:
also was very quick and kind with the responses to all our questions
excellent house and host
heather was an amazing host and very friendly
they are very harmless friendly creatures that love to interact with people
Location:
take a walk through this carefully designed paradise corner
this house this location and this environment is the best i’ve ever stayed in
what a perfect home for a 3 generation family holiday something for everyone and the location was ideal
Cleanliness:
great clean place with many extras
house itself is very clean spacious and cozy
the home was very clean and the homeowner was very responsive
Amenities & Room:
great views from pool area sitting area beach and master
Read more reviews

5. Searenity; Marathon (from USD 3259)

Best for: Outdoor enthusiasts, group trips, watersports enthusiasts

Book a stay in Searenity if you’re looking for a terrific summer vacation. This Airbnb comes with features perfectly suited for summer cookouts. You can use the fish cleaning station to process your catches of the day as well as an outdoor fridge and grill for meal preparation. When you’re done grilling, you can enjoy your meals inside the tiki hut.

Moreover, bring your boat when you make your way to Searenity and keep it tied to the provided dock. Two kayaks are also provided, so you’ll be able to explore the water nearby even if you don’t have a boat. If you’d rather spend the day relaxing at this wonderful house, you can always hop into the pool and turn on the jets.

Marathon, Florida, United States

143.39 km (89.1 mi) from Miami Seaquarium
77 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 4 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Host:
the owner was very quick with communicating overall a wonderful experience
the host is very easy to reach and replies rather quickly to messages
extremely friendly and responsive
super fast communication with the host
Location:
very nice house in a great location
this was a fabulous stay in marathon the location is close to everything and the house was perfect
great house in quiet neighborhood
clean and awesome location since we primarily fish in the gulf
the location is perfect and the outdoor tiki which we spent most of our time was very relaxing
Cleanliness:
very clean and tidy
it was very clean comfortable and well equipped
absolutely amazing very very clean
as the other reviews mention it is very clean and well maintained
Amenities & Room:
the beds were comfortable and the bathrooms were perfect for our family
the beds were very comfortable
the pool is just the right size for kids to have fun in and adults to chill
Read more reviews

6. Tropicasa; Key Largo (from USD 1440)

Best for: Nature lovers, group trips, watersports enthusiasts

Treat yourself and your friends to a memorable tropical vacation by staying in Tropicasa. Found on this 2.5-acre (1.0 hectares) Airbnb property are coconut trees with hammocks tied to them, ideal for an afternoon nap. There’s also a pier nearby you can use for fishing along with kayaks and paddle boards that are reserved for the more adventurous members of your traveling party.

Besides the outdoors, enjoy your vacation by having some drinks inside the home. There’s a full bar available for guests to use and a spacious dining area suitable for large groups. If you like, you can also head outside and use the provided grill to prepare the fish you and your friends caught earlier in the day and have a fun barbecue party.

Key Largo, Florida, United States

76.87 km (47.8 mi) from Miami Seaquarium
91 reviews   Wifi Available
ENTIRE HOME 6 Beds 12 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Host:
tanya was a great host
everyone on staff is super helpful and sweet
the staff on the property was super helpful
the property manager tom was helpful and friendly
on top of that tanya and the manager are so kind and responsive
Location:
located in a great location
the location was awesome
beautiful property and amazing location
the housr and location is just amazing
fabulous location highly recommend this house
Cleanliness:
well maintained and super clean
just book it the house is spacious and clean with plenty of gathering spaces and a well equipped kitchen
great place to stay very spacious and clean everything we needed in the kitchen
Amenities & Room:
the accommodations are very comfortable and roomy the views are spectacular
loved all the space in the kitchen
we enjoyed making use of the kitchen and outdoor grill
it fit 11 ladies very comfortably and had a huge kitchen and living area
Read more reviews

7. Island Dreamz Bay House; Marathon (from USD 5164)

Best for: Families, outdoor enthusiasts

Island Dreamz Bay House allows guests to create 5-star dining experiences of their own. In the morning, you can use the Keurig coffee maker to brew up some delicious beverages for your friends and family. You’ll also feel like you’re cooking in a high-end kitchen thanks to the quartz countertops and the provided Kitchen-Aid appliances. Fish-cleaning tables and gas grills are also available if you need them.

When it’s time to eat, you can stay inside or use one of the outdoor dining spots here. On that note, the waterfront gazebo is a great spot to enjoy your meal. You can have a delectable meal out on the open balconies as well.

Marathon, Florida, United States

141.43 km (87.9 mi) from Miami Seaquarium
69 reviews   Wifi Available
ENTIRE HOME 6 Beds 12 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 12

Top guest reviews
Host:
the hosts were super friendly and always had a quick response to anything we needed
lauri was a great host too and made sure we were happy with our stay from start to finish
lauri was a great host with excellent communication
this place was a fantastic stay beautiful location and the hosts were beyond our expectations
Location:
great place great location right on the canal
great location for families and children
place was great beautiful location
location was perfect for us as short outings were what we did
absolutely perfect location great communication from the owner
Amenities & Room:
the furniture inside and outside was tasteful and comfortable
my family loved the pool and deck
the layout was perfect for gathering in the living/dining room and flowing out onto the covered deck space
great pool and dock access that we used often would def recommend
the pool area was a good size for lounging as well as playing in the pool
Read more reviews

8. Blu on White; Key West (from USD 21960)

Best for: Pet parents, group trips, families with kids and infants

Celebrate a special event in style by staying at Blu on White. This Airbnb is ideally suited for entertaining due to its modern kitchen. It is an open-concept space outfitted with the latest appliances. Because of the way the kitchen is designed, you’ll be able to cook for your friends and family while also sharing stories with them.

Furthermore, the centerpiece of Blu on White’s outdoor landscape is the heated saltwater pool with jets for ultimate relaxation. Also, saltwater pools are gentler on the body, making the pool ideal for a swim after a busy day. Moreover, this rental allows pets too, so you can share this adventure with your fur babies.

Key West, Florida, United States

209.58 km (130.3 mi) from Miami Seaquarium
8 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Host:
we were there to host our sons wedding and shawn’s home was a perfect home base
shawn is a fantastic host and romi & her husband were so helpful throughout our stay
shawn and his management team are terrific and very responsive
shawn is a very responsive host and we would love to rent from him again
Location:
the location couldn’t be better
we loved cooking in the gourmet kitchen floating in the pool and walking to all our favorite spots
Amenities & Room:
the house is beautifully designed with lots of special details and very comfortable
Read more reviews

9. Atlantis; Cudjoe Key (from USD 2037)

Best for: Watersports enthusiasts, families with kids

Atlantis is an Airbnb property that gives guests plenty of opportunities to explore the waters of Florida Keys. Take your boat when you visit here and use the provided dock and marina to keep it safe and accessible. The kayaks and the swimming ladder attached to the sea wall will also help you and your fellow guests explore the area around the property.

Of course, you don’t need to go into the ocean just to relax in the water. Atlantis also offers a heated swimming pool and a hot tub if you’re looking for more leisurely experiences. Besides, there is a kids’ pool here too, so your little ones can be safe and have fun splashing. You can also enjoy some spectacular ocean views while lounging around Atlantis.

Cudjoe Key, Florida, United States

178.69 km (111.1 mi) from Miami Seaquarium
159 reviews   Wifi Available
Entire cottage 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Host:
manuel is a great host answers any questions promptly
manuel & alan were also excellent hosts
manuel is a great host
great spot and a great host would recommend to anyone in the lower keys area
manuel was a great host and we would definitely recommend
Location:
this is a perfect location
properties are pretty close together
what a wonderful location to watch every sunrise
this is florida keys paradise and this location came as advertised
great location perfect for fishing kayaking paddle boarding
Cleanliness:
on-site pool was clean and local community was friendly
great place to stay very nice and clean
wish they weren't so on top of each other but everything was awesome clean and better than expected
beautiful sunrises lots of amenities great location very clean great communication
atlantis was clean comfortable and beautiful and had just about the most perfect view one could ask for
Amenities & Room:
fantastic views beautiful kitchen and comfortable beds
beautiful view nice pool and swimming area
community pool was great and looked like it was recently re done
Read more reviews

10. Penthouse suite with unobstructed views; Key Largo (from USD 1968)

Best for: Nature lovers, group trips

Key Largo is one of the most beautiful islands in Florida Keys. You’ll develop a newfound appreciation for Key Largo’s beauty after staying in this penthouse suite. The unobstructed views allow you to see the best of what Key Largo has to offer in terms of natural splendor. Also, the oceanfront balcony is an ideal spot for romantic moments with your significant other.

Aside from the views it provides, this penthouse suite also impresses with its interior décor. The polished marble flooring and granite countertops are luxurious accents that elevate this property’s design scheme. Modern fixtures and appliances round out the high-end offerings here.

Key Largo, Florida, United States

79.29 km (49.3 mi) from Miami Seaquarium
40 reviews   Airbnb superhost icon Superhost Wifi Available
Entire villa 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Host:
fernando was a wonderful host and the condo was everything promised
the guard staff checks you in it was flawless and seamless
very responsive accommodating and helpful
we would most definitely stay here again and would highly recommend fernando as your host
Location:
recommend this location highly
beautiful location and well-kept condo
wonderful a great place to stay in key largo
Cleanliness:
very clean well apportioned
Amenities & Room:
nice amenities (pools hot tubs game room gym basketball tennis etc
however the hot tub at this pool is giant beautiful looks like a cave with waterfalls
the property was very clean beautiful furniture for relaxing and a great kitchen
Read more reviews

11. Glamorous Mediterranean-style rental; Key Colony Beach (from USD 5800)

Best for: Group stays, nature lovers

A lovely brick-paved pathway will take you to this Mediterranean-style mansion rental that has a lovely fountain in the front. As soon as you walk in, you’ll notice the gleaming interior, complete with plush furnishings, polished floors, and ornate touches.

The huge private pool with a pergola and the ocean can be seen from the back balcony, while the front balcony offers a beautiful view of the clear blue sky and healthy green foliage of various trees and plants.

To unwind, you may take a dip in the hot tub with a view.

Key Colony Beach, Florida, United States

142.15 km (88.4 mi) from Miami Seaquarium
12 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 5 Beds 10 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 10

Top guest reviews
Location:
the neighborhood and location was perfect for our family trip
Cleanliness:
the house was incredible and so clean
algae growing on the bottom of it and it looked like it hadn’t been cleaned for months
Read more reviews

12. Luxurious home at Marlin Bay Resort & Marina; Marathon (from USD 7554)

Best for: Families, group trips

This 3,600-square-foot (334.5-square-meter) home at Marlin Bay Resort and Marina is the ideal setting for relaxation, with a number of balconies providing breathtaking views of Florida Bay. The interior features big glass windows and doors, marble flooring, and expensive décor throughout. Everything is of the highest quality, from the fully equipped kitchen with stainless steel appliances to the bed linens and plush pillows in the bedrooms.

You have access to a heated pool and hot tub, as well as a marina where you can enjoy a barbecue cookout!

Marathon, Florida, United States

146.74 km (91.2 mi) from Miami Seaquarium
4 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 6 Beds 10 Guests 4 Bedrooms 5 Bathrooms

Accommodates: 10

Top guest reviews
Host:
staff (especially barbara) was super helpful and friendly
Location:
amazing place definitely will be back
Cleanliness:
the place was super clean and felt just like home
Read more reviews

13. Casa Cristol; Key West (from USD 1100)

Best for: Group trips, families with kids and infants, pet parents

Casa Cristol gives visitors the freedom to choose whichever vacation experience they wish to have. Would you prefer to enjoy a more relaxed stay in Florida Keys? If so, the secluded location of this Airbnb property will suit you well. You can make your way to the private patio and soak in the tropical atmosphere of your surroundings. Feel free to use the property’s fully equipped kitchen to prepare your favorite meals.

Also, visitors hoping to have a livelier vacation can take the short walk from Casa Cristol to Duval Street. Notable Duval Street attractions include Sloppy Joe’s and Red Barn Theatre. Numerous art galleries and restaurants also line the area.

Key West, Florida, United States

210.87 km (131.1 mi) from Miami Seaquarium
336 reviews   Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
Host:
the host was pleasant on point and attentive to our needs
our host graciously let us check in early
mike was a terrific host
our host was easy to contact and very accommodating to our needs
nice pool and helpful host
Location:
fantastic location walk anywhere
the location was perfect and within walking distance to everything
great location that is both quiet but close to all the fun stuff
this house has a great location where you can walk everywhere
great location my family has visited kw for a very long time
Cleanliness:
it was impeccably clean and maintained
it was very clean
house was sparkling clean
everything comfortable and clean
nice clean accommodations in a tropical setting even for key west
Amenities & Room:
the furniture was comfortable and modern
the outdoor space was private and peaceful with lounge chairs a dining table and a grill
also an awesome back deck and kitchen for entertaining
all the staples in the kitchen made for easy cooking
the beds are incredibly soft our favorite aspect was the private deck and yard
Read more reviews

14. Majestic estate facing the ocean; Key Largo

Best for: Group trips, nature lovers, beach lovers

This enormous estate is located about 45 minutes from Miami International Airport and exudes exquisite grandeur. As soon as you enter, you’ll notice the beautiful, opulent decor, which includes polished marble flooring, elegant spiral staircases, and leather sofas.

All the rooms boast grand chandeliers and glass windows that let in natural light. You can watch TV or play the piano in the living room whenever you like. The two large outdoor balconies with views of the ocean offer the perfect setting for al fresco dining. An outdoor pool is also available, where you can swim while admiring the views.

Key Largo, Florida, United States

61.87 km (38.5 mi) from Miami Seaquarium
PRIVATE VACATION HOME 11 Guests 5 Bedrooms 4 Bathrooms

Top guest reviews
Host:
we thoroughly enjoyed our stay and thank the hosts for sharing this exquisite property and home with us
rob was fantastic as property manager and couldn't have been more helpful and responsive
Location:
the home is beautifully situated on a cul-de-sac offering privacy and ample space to park cars
Read more reviews

15. Charming house rental with a hot tub; Key West

Best for: Group stays, families

This charming house rental has two studio-style suites that are well furnished with modern amenities to provide you with conveniences such as air-conditioning, wireless internet, and a flat-screen TV.

Each suite has a seating area, one leads to the balcony, and the other leads to the patio. On the balcony, you can have a cup of morning coffee and enjoy watching the beautiful sunrise. While on the patio, relax and unwind as you soak in the tub to relieve some stress.

Key West, Florida, United States

210.63 km (130.9 mi) from Miami Seaquarium
Wheelchair accessible Visual Aid: Braille
cottage 4 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the check-in the accommodations the owners and of course the location were all amazing
Location:
great location very comfortable beds
location was outstanding right off duval in the middle of everything
great location very nice place
very nice layout of the property and close to duval
perfect location for key west steps from duval street
Read more reviews

16. Amazing vacation rental on an exclusive island; Marathon

Best for: Pet parents, group stays, families with kids

This amazing vacation home is located on the exclusive Tingler Island. It features stunning ocean views from every corner of the house and a lovely outdoor pool that you can take advantage of during your stay.

Furthermore, this house has an open-plan living space and is equipped with air-conditioning and heating systems to provide you with comfort, as well as access to the internet for your convenience. Plus, each room has a balcony that overlooks the ocean and there is also a deck that has the best view of the beautiful sunsets.

Marathon, FL, US
10 Guests 4 Bedrooms 4 Bathrooms

17. Lavish waterfront home with a mini golf; Marathon

Best for: Group trips, outdoor enthusiasts, families with kids and infants

For a fun and relaxing getaway, book a stay in this lavish waterfront home. It features a beautiful outdoor pool that sits right next to the gulf, offering stunning views of sunrise and sunsets. There are also two tandem kayaks on the property that you can use to fully enjoy the water. Other entertaining amenities include bicycles, a mini golf course, skee-ball, indoor basketball, and darts.

Furthermore, the house is complete with comfy seating areas, indoor and outdoor dining spaces, and a kitchen that is equipped with stainless steel appliances. Families traveling with kids will also find the pack and play, high chair, and stroller useful.

Marathon, Florida, United States

142.65 km (88.7 mi) from Miami Seaquarium
PRIVATE VACATION HOME 8 Guests 3 Bedrooms 4 Bathrooms

Top guest reviews
Host:
very responsive management by owner
communication with the hosts was outstanding i can not recommend this vacation home enough
Location:
fantastic house and location great for kids
unbelievable property and location ideal for boaters wanting easy access to the ocean or florida bay
the location is superb - both locale in maraton as well as locale on the water
fantastic location plenty of space beautifully appointed and maintained lots of things to do indoors and out
Cleanliness:
the home was well appointed clean etc
Amenities & Room:
game room was a hoot and putting greens led to some friendly wagering
it inspired us to follow suit the pool was relaxing…
Read more reviews

18. Fully furnished paradise with a heated saltwater pool; Long Key

Best for: Nature lovers, beachgoers, watersports enthusiasts, group trips

Unbeatable views of Florida Bay are not the only thing to be enjoyed in this rental. The property also boasts a large and heated saltwater pool and a dock. Its spacious gazebo features outdoor seating as well as a grill for cooking the day’s catch. It’s an ideal spot to relax and watch the boats and kayaks that pass by. As this rental is centrally located between Islamorada and Marathon, guests can easily reach parks, museums, shops, and restaurants.

Inside the rental are 3 bedrooms and 3 full bathrooms, suitable for accommodating a total of 10 guests. Air conditioning and heating are available. Wi-Fi, games, and a TV are also provided for entertainment. 2 kayaks already come with the rental. Guests who want to try water adventures can arrange for paddleboard, Jet Ski, and boat rentals.

Long Key, FL, US
10 Guests 3 Bedrooms 3 Bathrooms

19. Oceanfront haven with a private rooftop terrace; Marathon

Best for: Group stays, families with kids

Boasting a private rooftop terrace, this oceanfront retreat provides a luxurious getaway in the heart of the Conch Republic. Take in the beautiful sunset views and watch the luxury yachts that pass by. If you want to take a break from the salty waters of the ocean, you can also opt to swim in the community pool located just a short distance away from the property.

Featuring three bedrooms and three full bathrooms, this rental is suitable for up to eight guests. It is also equipped with air conditioning, Wi-Fi, flat-screen TVs, and a private elevator. The kitchen is fully equipped with cooking basics and essentials, perfect for home cooks who want to prepare the day’s catch. For guests with a car, the ground floor has covered parking available.

Marathon, FL, US
8 Guests 3 Bedrooms 3 Bathrooms

20. Deluxe hideaway with a private dock; Marathon

Best for: Group stays, families with kids, watersports enthusiasts

Nestled in Indigo Reef Resort in Marathon, this luxurious hideaway is ideal for a total of eight guests. It offers three bedrooms, three bathrooms, and a fully furnished kitchen. The place is equipped with heating and comfort as well. For entertainment, guests are provided with Wi-Fi, games, and a TV. Lounging by the shared pool and watching beautiful sunsets from the front porch are some of the relaxing things to do in this rental.

With a private dock on the property, guests can bring their boat and enjoy adventures in the waters.

Marathon, Florida, United States

140.82 km (87.5 mi) from Miami Seaquarium
PRIVATE VACATION HOME 8 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
our host john was very responsive to questions
Location:
perfect location off the main strip yet close enough to do thing
we definitely plan to return to this location
marathon is a great location to be able to visit all of the keys
boat slip was great and close to the unit
what a great place to getaway
Cleanliness:
the unit was well stocked clean and had everything we needed
clean well equipped and a great location
we absolutely loved this property the pool is clean and plenty of chairs to relax on
Amenities & Room:
it was spotless the furniture was comfortable and the view is outstanding
the pool is very close and the views of the palm trees and water were very relaxing
Read more reviews

21. Waterfront condo with a private hot tub; Key West

Best for: Group trips, outdoor enthuiasts

Cozy yet fully furnished, this one-bedroom condo is situated on the sixth floor of Galleon Resort & Marina. It is close to Duvall Street, Mallory Square, and Key West Shipwreck Museum. Guests can enjoy easy access to several attractions and dining options during their stay.

This rental also offers a full bathroom, a dining area, and a well-equipped kitchen. With three beds in the unit, it can comfortably sleep a total of five guests. Other indoor features include Wi-Fi, air conditioning, and cable TVs. There is a private hot tub ideal for end-of-the-day soaks as well. A spiral staircase also leads to a private rooftop deck with scenic Key West views.

Key West, Florida, United States

210.28 km (130.7 mi) from Miami Seaquarium
condo 5 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Host:
the staff is great
this owner clearly knows how to take care of his guests
our host ed answered any questions we had and was very easy to work with
thank you to the owners for letting us stay at their property
Location:
good location and loved the apartment
good location and nice pool and beach area
a great place to relax and also close to all that key west has to offer
great place very unique and fun extremely private
Cleanliness:
the unit was very clean and spacious
clean like i have never seen
Read more reviews

22. Stunning house in a gulf front property; Islamorada

Best for: Nature lovers, group stays

Located in the midst of lush greenery, this fabulous property will ensure you have a delightful vacation. It offers breathtaking views of Everglades National Park which is famous for backcountry fishing. The apartment is easily accessible from Snake Creek or Tavernier Creek as well as deep sea fishing or scuba diving in the Atlantic Ocean.

The apartment offers some great facilities such as a recreational room, a swimming pool, internet access, TV, parking facilities, high-tech appliances, a washer, a dryer, and a fireplace.

Islamorada, Florida, United States

93.77 km (58.3 mi) from Miami Seaquarium
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 4 Bathrooms

23. Gorgeous vintage cottage in the heart of Old Town; Key West

Best for: Families, group stays

Located in one of the most popular areas of Old Town, Key West, this luxury cottage is the ideal getaway for a squad of four. The interiors are tastefully decorated with open beam ceilings and muted tiles. The bathroom and kitchen are oozing with extravagance and with exquisite decor and appliances. There is a spacious courtyard outdoors which sports some of the prettiest flowers, making it a view worth remembering.

The location is to die for as well with all the major attractions at your disposal. Famous restaurants, art galleries, bakeries, coffee shops, jazz clubs are all within the vicinity. The amenities offered here include a swimming pool, a washer and dryer, air-conditioning, TV access, and internet facilities.

Key West, Florida, United States

210.67 km (131.0 mi) from Miami Seaquarium
PRIVATE VACATION HOME 4 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Host:
the heated pool was amazing
it took us literally until the end of our trip to figure out where to put the trash and recycling bags outside
We are trying to figure out how we can get back for another week
we all did have a great time
a couple of times Had problems with the dryer but they are in the middle of repairing
Location:
Restaurants and shops are a short stroll away
The location was great close walking distance to everything
The property manager Paige addressed it right away and got it fixed the next day (on a Saturday)
the Luxury Vintage Cottage is the perfect place to stay at in Key West
We rented bikes from Fury around the corner
Cleanliness:
The pool was clean and very relaxing
Everything was spotlessly clean and we enjoyed daily swims in the pool and dinners on the terrace
Amenities & Room:
The fan overhead in the bedroom was nice to have on at night; however it was not totally secured/stable to the ceiling
There is a parking space in front of the property and one can easily reach any place in the old town on foot
Very private just off the quiet end of Duval Perfect size for a couple - could have four people but might be a little cramped
The property was excellent loved hanging by the private pool
The outdoor dining area under the porch could have been made more comfortable with the addition of pads on the chairs and the adjoining sitting area under the porch would have been more enjoyable w...
Read more reviews

24. Luxury property with a gorgeous pool area; Key Largo

Best for: Families with kids, celebrations, group stays

This luxury mansion sprawling over 5,000 square feet (1524 square meters) is surrounded by lush greenery and boasts breathtaking views of the Atlantic Ocean from every room. In the well-lit art kitchen, you’ll find a double refrigerator, beautiful wooden cabinetry, granite countertops, and 18 seats, which are ideal for an elaborate meal with family or friends.

For those who’d like to spend a beautiful day outside, the pool area with the tiki hut and loungers is excellent. It’s nestled amidst greenery and affords gorgeous water views.

Key Largo, Florida, United States

65.87 km (41.0 mi) from Miami Seaquarium
PRIVATE VACATION HOME 17 Guests 6 Bedrooms 5 Bathrooms

Top guest reviews
Location:
restaurants within walking distance for local seafood and drinks was a nice change
there were fishing snorkeling charters going out etc yet was really quiet and peaceful
being in the location it is had a lot of boat traffic which was great
we look for a beautiful house which is well located and large enough for our entire family
Amenities & Room:
the pool was very nice and the yard was great to chill
the screened in area off the kitchen was a favorite place to sit and relax
Read more reviews

25. Waterfront estate surrounded by nature; Islamorada

Best for: Beach lovers, watersports enthusiasts, nature lovers, group stays

You’ll fall in love with this luxurious oceanfront mansion that has been beautifully refurbished and is framed by lush palm trees. There are hammocks, loungers, and a private pool in the five-bedroom house, guaranteeing complete relaxation. You can enjoy yourself by fishing from the pier or going kayaking right from your backyard! Two kayaks and two paddleboards are at your disposal. A basketball court has also been provided for your enjoyment.

When you’re hungry, prepare your favorite dinner in the well-stocked kitchen and enjoy an open-air feast on the upstairs terrace. Later, you can sip a drink underneath the lovely tiki hut.

Islamorada, Florida, United States

112.31 km (69.8 mi) from Miami Seaquarium
PRIVATE VACATION HOME 12 Guests 5 Bedrooms 6 Bathrooms

Top guest reviews
Host:
the owner/manager was very responsive to our questions in advance
Location:
lo key was probably one of the best places we have ever rented
Cleanliness:
the house is clean and spacious and the owners provide everything you need
Amenities & Room:
we loved the pool paddle boards rooftop deck and chickee hut
the bedrooms with private baths were very comfortable
beds were so comfortable
Read more reviews

26. Beautiful home rental with a private pool; Key West

Best for: Group stays

This beautiful home rental features a private backyard pool where you can have fun swimming and sunbathing during your vacation. Its large living space is complete with all comforts of the home such as air-conditioning, heating systems, and high-speed internet.

Inside the house, there are plenty of spaces for you to hang out and watch movies. There is also a roomy kitchen that is equipped with modern facilities, so you can easily prepare delectable meals. Additionally, dining areas are available indoors and outdoors for a full experience of the property.


210.53 km (130.9 mi) from Miami Seaquarium
136 reviews   Wifi Available
House 14 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 14
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Host:
property manager was awesome and communicative
don’t know the hosts cost but it’s worth it
the house manager was super friendly and just a text away at all times
the communication with the owner was smooth and they were very friendly
Location:
great location of the house
location was excellent especially close to duval and the bars
this location was absolutely perfect to walk around key west
the location was perfect could walk everywhere
house was perfectly situated in the heart of key west steps from duval street
Amenities & Room:
such a cool old house with plenty of room to spread out
the pool was great and we had everything we needed
the house itself was huge and had a great backyard with dipping pool
great backyard with a pool and 2 different balconies plus a front port and patio
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27. Lovely abode with a private pool; Key West

Best for: Outdoor enthusiasts, group stays

Casa Amor offers a stay that is just as lovely as its name. What used to be a bottling plant is now a luxury retreat in the heart of Key West. This contemporary gem boasts a lush backyard oasis and a covered patio that overlook the private pool with a waterfall. The place also offers 3 bedrooms with flat-screen TVs, ideal for sleeping a total of 10 guests. It also has 3 bathrooms and an updated kitchen with a bar.

Other features of this rental include air conditioning, internet access, a gas grill, and an off-street parking spot.


210.3 km (130.7 mi) from Miami Seaquarium
176 reviews  
House 10 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 10
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Host:
propert manager was very responsive to questions
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
ideally located within walking or biking distance to just about everything
the location was perfect for our family
it’s location is great being within walking distance to everything whether it be the beach or duval street
plenty of room and a great location
i highly recommend this location
Cleanliness:
thanks again to shana

the house was impeccably clean
Amenities & Room:
the pool deck was nice and private
pool area can get slippery so a bath mat for the doorway would be safer
the house was spacious and accommodating with a beautiful lanai and pool area
Read more reviews

28. Superb luxury apartment with fabulous amenities; Key West

Best for: Group stays

This gorgeous apartment has everything you could want in a vacation rental. It is oozing with utmost comfort and is located in a supremely tranquil neighborhood. It is located in the Casa Marina East district of Key West which is equidistant to the beach and to the Old Town.

With exquisite French decor, the interiors are very well done up and showcase elegance and utmost charm. The swimming pool area here is super spacious and is the perfect place to spend a relaxing evening. The other amenities provided here include air-conditioning, a washer and dryer, a swimming pool, parking facilities, internet connection and lots more.

Key West, Florida, United States

209.15 km (130.0 mi) from Miami Seaquarium
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Host:
It was big and warm and the kids had hours of fun jumping in the deep end
so my husband could work remotely and my children shared the third bedroom which was also upstairs
We were traveling with three generations (my parents me and my husband and my two young children)
Location:
The house was set up perfectly for us
Amenities & Room:
the upstairs master bedroom had a large attached office
My parents stayed in the downstairs bedroom
Their was plenty of space for all six of us
And the pool was lovely
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29. Charming and relaxing villa

Best for: Beach lovers, group stays

This gorgeous luxury villa is an abode of great amenities and offers mesmerizing ocean views. It is situated at a great location and has been renovated with all the necessities that one would need for a hassle-free stay. The bedrooms are oozing with comfort and are perfectly equipped with large king-sized beds and ceramic tile floors.

The house is simply decorated and is sparkling clean. The rental is close to all the major attractions of the area. Some of the facilities offered here include air-conditioning, a heater, a washer and dryer, internet access, a TV and parking facilities.


209.02 km (129.9 mi) from Miami Seaquarium
18 reviews  
House 6 Guests 3 Bedrooms 3 Bathrooms
Top guest reviews
Host:
Bruce was a wonderful host and very responsive
Mardee could not have been more helpful
either and very well-maintained
the caretaker is more than helpful and a wealth of information
We've been pretty happy with all our rentals all through VRBO
Location:
it's really in a great location
Not a bad morning or afternoon walk to Duval Ability to walk (about 7 minute stroll) to beach every evening
and it's easy to get anywhere quickly
It's not far from grocery and other stores on Roosevelt Blvd
Cuban Coffee Queen also makes lousy coffee
Cleanliness:
The pool area is exactly as pictured
Amenities & Room:
to have our very own pool in the backyard
The house is well-equipped and up to date
I felt like I was on a month long retreat
the proximity to the airport is an extra bonus (6 minutes)
was so relaxing the privacy perfect
Read more reviews

30. Modern and fully equipped apartment; Key Largo

Best for: Senior citizens, group trips

Located on Sunrise Cay, this luxurious apartment for 12 is cost-efficient and is super comfortable as well. It is centrally located and fully equipped with all the facilities one would need for a delightful stay. The four bedrooms here are super spacious and the interiors are very well done up. They are modern and contemporary with intricate detailing to accentuate the whole setting.

The house offers other luxurious facilities such as a fitness center, a recreation room with a pool table, ping pong, flat screen TV’s, barbeque facilities, an elevator, internet, and parking as well.

Key Largo, FL, US

48.06 km (29.9 mi) from Miami Seaquarium
House 8 Guests 3 Bedrooms 3 Bathrooms

31. Outstanding beach villa with panoramic views; Islamorada

Best for: Group trips

This swanky four-bedroom villa is oozing with utmost luxury and comfort. It has a phenomenal location and offers mesmerizing ocean and beach views. The interiors are tastefully decorated and the rooms are fully equipped with sky-high ceilings, gourmet kitchens, magnificent balconies and lots more.

Besides this, the other amenities offered include a heated pool and spa, internet connection, air-conditioning, a washer and dryer, parking facilities, central heating, and TV.

89051 Old Hwy

92.0 km (57.2 mi) from Miami Seaquarium
2 reviews  
House 10 Guests 4 Bedrooms 5 Bathrooms

32. Centrally located apartment for eight; Key West

centrally located apartment for eight; key west
Source: Vrbo

Best for: Beach lovers, group stays

This five-star beach house has been a major crowd puller right since its inception and is the ideal accommodation for large groups of eight people. It has a fantastic location and is just minutes away from the gorgeous beach, the marina and lip-smacking eateries.

The high-quality beds coupled with the fancy features will make every penny worthwhile. The house is equipped with high-tech, modern amenities such as large-screen TVs, a home theatre, a wine fridge, a huge island seating at the kitchen bar, air-conditioning, internet connection, hot tub, parking facilities, a washer, and a dryer.

Key West, FL, US
8 Guests 3 Bedrooms 4 Bathrooms

A relaxing getaway

The Florida Keys is truly a magnificent place to feel absolutely relaxed and rejuvenated. The luxurious vacation rentals mentioned above will surely make your stay delightful with the best of amenities and facilities at your disposal.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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