13 Luxury Rentals In Florida Keys, Florida

Roohi
Roohi 
Updated
| 3 min read

The Florida Keys are a stretch of tropical islands located off the southern coast of Florida. It is a coral cay archipelago which 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 makes 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.

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 June 21, 2023.

1. Beautiful home rental with a private pool (from USD 1250)

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.

Stayed at this 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
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
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
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2. Gorgeous waterfront house with a pool and spa (from USD 1016)

This gorgeous waterfront house is a cozy accommodation that is best for big families and groups of friends. It spreads over two floors and features a beautiful outdoor pool with a spill-over spa.

This vacation house is well equipped with modern amenities such as wireless internet, air-conditioning, a heating system, and an elevator. You will also be provided with access to the on-site parking if ever you are traveling by car. Furthermore, this rental boasts a game room with a ping pong table to keep you entertained indoors.

Stayed at this property?

142.17 km (88.4 mi) from Miami Seaquarium
19 reviews   Wifi Available
House 12 Guests 5 Bedrooms 7 Bathrooms

Accommodates: 12
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the two kitchens and outside grill were well stocked and space was perfect for everyone
we loved the five large bedrooms with comfortable bedding generous closets and en-suite bathrooms
we spent most of our days lounging around the gorgeous pool and hot tub
Cleanliness:
incredibly clean and the kitchen was very well-stocked
this entire property is spectacular the house is impeccably clean and beautifully decorated
Host:
our host monica was helpful and responded immediately to our questions
the property manager monica was awesome and very responsive to everything we needed
property manager was very accommodating to our special needs property exceeded our expectations
communication with the owner was perfect
Location:
the neighborhood is pretty and bustling with people walking/bike riding
house provided the perfect backdrop and location for our time in marathon
this neighborhood is beautifully maintained quiet and safe
sunset park became our favorite place to watch the sunset before walking back to the house
the pool and hot tub were lovely and the location was very good as well
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3. Charming house rental with a hot tub (from USD 625)

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.

Stayed at this property?

210.63 km (130.9 mi) from Miami Seaquarium
82 reviews  
cottage 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

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
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4. Amazing vacation rental on an exclusive island (from USD 715)

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.

Stayed at this property?
Marathon, FL, US
10 Guests 4 Bedrooms 4 Bathrooms
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5. Lavish waterfront home with a mini golf (from USD 733)

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.

Stayed at this property?

142.65 km (88.7 mi) from Miami Seaquarium
17 reviews   Wifi Available
House 8 Guests 3 Bedrooms 4 Bathrooms

Accommodates: 8
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
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…
Cleanliness:
the home was well appointed clean etc
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
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6. Fully furnished paradise with a heated saltwater pool (from USD 1083)

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.

Stayed at this property?
Long Key, FL, US
10 Guests 3 Bedrooms 3 Bathrooms
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7. Oceanfront haven with a private rooftop terrace (from USD 365)

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.

Stayed at this property?
Marathon, FL, US
8 Guests 3 Bedrooms 3 Bathrooms
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8. Lovely abode with a private pool (from USD 677)

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.

Stayed at this property?

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
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
Cleanliness:
thanks again to shana

the house was impeccably clean
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
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9. Deluxe hideaway with a private dock (from USD 414)

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.

Stayed at this property?

146.9 km (91.3 mi) from Miami Seaquarium
44 reviews   Wifi Available
townhome 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
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
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
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
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10. Waterfront condo with a private hot tub (from USD 450)

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.

Stayed at this property?

210.28 km (130.7 mi) from Miami Seaquarium
76 reviews   Wifi Available
condo 5 Guests 1 Bedroom 1 Bathroom

Accommodates: 5
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Cleanliness:
the unit was very clean and spacious
clean like i have never seen
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
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11. Superb luxury apartment with fabulous amenities (from USD 270)

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.

Stayed at this property?
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
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
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
Read more reviews
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12. Stunning house in a gulf front property (from USD 1850)

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 to the 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.

Stayed at this property?
Islamorada, FL, US
93.77 km (58.3 mi) from Miami Seaquarium
House 8 Guests 4 Bedrooms 4 Bathrooms
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13. Gorgeous vintage cottage in the heart of Old Town, Key West (from USD 392)

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.

Stayed at this property?

210.67 km (131.0 mi) from Miami Seaquarium
21 reviews   Wifi Available
cottage 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4
Minimum Nights: 0
Refund Policy :

Top guest reviews
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...
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
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
Read more reviews
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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.

Stayed at this property?
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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