29 Best Airbnb Vacation Rentals In Islamorada, Florida - Updated 2024

Deanna
Contributing Writer
Updated
| 13 min read

Islamorada is a lovely village with turquoise waters, pristine sandy beaches, and six beautiful islands. This place is also renowned as the “Sportfishing Capital of the World,” attracting many fishing enthusiasts. Visitors can explore the underwater world by diving with assistance from Islamorada Dive Center. If you want to learn more about diving, head to History of Diving Museum. The sealife here is colorful and the kids will have a blast watching animal tricks in Theater of the Sea, a marine mammal park. You’ll learn much about local lore and major hurricane events in The Florida Keys History and Discovery Center. You can also rent a boat and try other things to do - just remember, while you are charting your itinerary, you must also prioritize finding a place to stay. Read about the top Airbnb vacation rentals in Islamorada, Florida, below.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on August 21, 2024.

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1. Oceanfront getaway with swimming pool (from USD 828)

Best for: Beach lovers, nature lovers, families, group stays

A three-bedroom beachfront rental awaits your party of eight at La Jolla Resort. The lovely house you’ll be staying in is ensconced among 2 acres (0.8 hectare) of tropical trees. The air is crisp and smells of the sea. There is unlimited outdoor seating. You have wide-open access to flamboyant sunsets that will be remembered forever. The house, beach, and pool are all yours for the time being and for a reasonable rate.

Stayed at this property?
Islamorada, Florida, United States
48.57 km (30.2 mi) from Everglades National Park
29 reviews   Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Location:
great location and roomy accommodations for our group
wonderful location beautiful scenery and great service
Read more reviews

2. Well-equipped cottage with pool access (from USD 259)

Best for: Families, group stays

A family of four will have a grand time in Islamorada when they stay at this bright, two-bedroom cottage in the small community of Shady Palms. The home is furnished with all that you need for a comfortable and convenient vacation, from a sunny living room with a television to a well-equipped kitchen and a washer-dryer combo. There’s also a private terrace for you to lounge in and enjoy the sun. Guests of this cheery home will have access to the community pool.

Stayed at this property?
Islamorada, Florida, United States
50.05 km (31.1 mi) from Everglades National Park
72 reviews   Wifi Available
Entire cottage 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
overall the cottage was very comfortable (especially the beds) and we would definitely come back
the cottage is tiny but comfortable for a family of four
cozy cottage is the perfect name - it was cozy and quaint
pool was beautiful and had a much fun with our neighbors
and the pool is perfect to take a dip
Cleanliness:
this is a clean cozy cottage
it was updated clean and well appointed
the villa was very clean and comfortable
a great little clean and stylish space with easy access to a nice clean pool
a very clean homey well equipped small home
Host:
we enjoyed meeting a few of the owners who shared restaurant tips with us
we had everything we needed and the host was very responsive
the host was responsive to messages and the check-in and check-our process was easy and smooth
we enjoyed meeting the friendly neighbors
carol was reaponsive friendly and helpful
Location:
nice location and cute house
great location and very private
cute place and very convenient
great location for us would come back again
still a good location for the price point though
Read more reviews

3. Pet-friendly villa with bay views (from USD 275)

Best for: Pet parents, couples, families

Are you looking for a pet-friendly Airbnb rental in Islamorada? Then you should check out this villa.

This one-bedroom villa hosted by Lloyd is suitable for up to four people. Named Bayside Villa, the rental is centrally located and is close to the city center, nightlife, and various family-friendly attractions. The place is pet-friendly, and guests may bring one small dog. This bohemian-like island home comes with a fully functional kitchen, as well as a cozy living room with a TV. When you book this unit, you may use the boat ramp and boat trailer parking nearby.

Stayed at this property?
Islamorada, Florida, United States
48.72 km (30.3 mi) from Everglades National Park
19 reviews   Wifi Available
Entire villa 2 Beds 4 Guests 1 Bedroom 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
the bed was comfortable too they have all the kitchen supplies you’d need
Host:
lloyd is a kind and responsive host
Location:
good house great location in town
it's a great place to stay
great location very clean nice to meet other's staying in the area
Read more reviews

4. Upscale villa with private beach and pool (from USD 400)

Best for: Beach lovers, families with kids and infants, group stays

The manager of this two-story villa in Anglers Reef is proud of the available space within and the additional amenities in the backyard. The private patio has a barbecue that has been prepped to let you cook your signature steak to perfection. You will feel secure staying inside an upscale neighborhood with your very own private beach and a swimming pool to boot.

Stayed at this property?
Islamorada, Florida, United States
48.43 km (30.1 mi) from Everglades National Park
28 reviews   Wifi Available
Entire villa 4 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
nice heated pool and beach area for those staying in the community
Cleanliness:
house was very clean modern and decorated beautifully
the house was very clean
her place was gorgeous clean and comfortable
this place is great super clean and spacious
this is an excellent place to stay very clean the gated community was well maintained
Host:
gina is absolutely a super host
gina is an awesome very personable host
gina was very responsive to any questions and a few small things that arose
gina was very quick to respond to our inquiries and was an excellent host
a great and attentive host nicely and comfortably furnished house
Location:
great location and community
we loved the location and the house was beautiful it has everything you need so just bring your clothes
the location is great for seeing all the keys have to offer
many places nearby with great music
a great place to stay
Read more reviews

5. Amazing townhouse with ocean views (from USD 4424)

Best for: Families with kids and infants, beach lovers, group stays

Superhost Walter offers a 3D virtual tour of Ocean Islamorada Beachhouse. Before clicking on it, you should know that the private listing easily accommodates six. Aside from the modern comforts of home, the Airbnb property in Islamorada has a boat dock at the front. You can sunbathe on the second-floor balcony or the sundeck in the backyard. The beach house is one-half of a duplex. Your host is gracious enough to offer you the better half–the one with an ocean view. Watch out for spectacular gulf sunsets. They will take your breath away.

Stayed at this property?
Islamorada, Florida, United States
50.59 km (31.5 mi) from Everglades National Park
19 reviews   Superhost Wifi Available
Entire townhouse 3 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the condo is very well stocked with towels and the kitchen is a full array of supplies
Cleanliness:
fantastic location large apartment with all we needed clean modern i recommend it
Host:
and it was all possible with the help of walter our host
he was so helpful and his place is great
Location:
wonderful place in a great location
we had an amazing vacation at walter's place
Read more reviews
Monthly discount: 21% off

6. Quaint cottage on the ocean (from USD 6615)

Best for: Watersports enthusiasts, pet parents, beach lovers, families, group stays

If you’re all about that tropical island vibe in a home, there’s no better place to stay than this oceanfront cottage hosted by Beverly. Four guests are comfortably accommodated in the two bedrooms. This vibrant home is on an acre (0.4 hectares) of land and warmly welcomes pets to stay with you too. The location of this charming Airbnb is close to Islamorada’s best bars and restaurants. Perhaps the best part of this home is the spacious patio facing the yard and the scenic waters. Take note that there is a floating house on the beach where the unit caretaker lives.

Stayed at this property?
Islamorada, Florida, United States
48.41 km (30.1 mi) from Everglades National Park
6 reviews   Wifi Available
Entire cottage 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

7. Bayside townhouse with sunset balcony and marina (from USD 330)

Best for: Families with kids and infants, beach lovers, group stays

A waterfront townhouse within the Futura Yacht Club gated community is available to a group of four holidaymakers who wish to see Islamorada’s true beauty. Superhost Claire wants to stress that the bayside listing has many sides facing the water. Aside from ample beach sand for frolicking or sunbathing, there is a heated pool as an alternative. A private marina is within property lines. If you’re feeling lazy and just want to look at the ocean, then sit on the balcony and take in the glorious view. You have all the time in the world.

Stayed at this property?
Islamorada, Florida, United States
48.93 km (30.4 mi) from Everglades National Park
74 reviews   Wifi Available
Entire townhouse 4 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
also the pool is huge heated and with plenty of lounge chairs
Cleanliness:
very clean space beautiful townhome
the place was very clean and nicely decorated
the condo was very clean spacious and well stocked
the townhouse was extremely clean and comfortable
the pool was beautiful clean and refreshing
Host:
claire was a wonderful host and she has a lovely home
claire is a wonderful host that exceeded expectations
claire is a very good host and answered very quick when i had questions
claire was an amazing host that was quick to respond and clarify any questions i had
highly recommend this rental and this host
Location:
the location is perfect
nice townhome with great location
great central location in the keys
so close to our new favorite restaurants
the location of claire’s place was perfect
Read more reviews

8. Luxurious sanctuary with access to dolphins (from USD 6972)

Best for: Couples, solo travelers, nature lovers, beach lovers

This gorgeous beachfront Airbnb vacation rental in Islamorada has one king bed and is far from the crowd. It’s perfect for couples who want to snuggle, snorkel, and explore the Everglades. A tiki lodge with hammocks is a bonus for those who cannot be parted from a view of the sea. This Airbnb on the Islamorada beachfront is absolutely perfect for a romantic weekend. Your Superhost has an important reminder about using only American-made sunscreen. It’s necessary to prevent stains on the expensive linen, you see. So, expect luxurious quarters and unforgettable ocean views at Secret Keys Waterfront Hideout.

Stayed at this property?
Islamorada, Florida, United States
50.81 km (31.6 mi) from Everglades National Park
265 reviews   Wifi Available
Private room in guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
beautifully decorated room with good amenities
fan tables lounges and hammocks) hanging over the water
we appreciated all of the extras in the apartment and of course the tiki hut
very cozy little place with a perfect king size bed you will love to sleep in
Cleanliness:
great stay exceptionally clean and loved the tiki hut
the room was sparkling clean
the space is spotless with many thoughtful touches
soooo relaxing the unit was super clean and stocked with lots of thoughtful items
room was clean all amenities worked well bed was just
Host:
great hosts that are very helpful with quick responses
our hosts were perfect
the hosts were very helpful in getting us settled in
hosts were responsive and accommodating
the hosts were readily available and respected our privacy
Location:
perfect for couples or close friends
the location was breathtaking and very private
we enjoyed the restaurants close by also
the location was great and easy to find
great location halfway between key largo and key west
Read more reviews

9. Pet-friendly home near the ocean (from USD 228)

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

Flakey’s Bed and Beer is a jewel at the very heart of Islamorada. It’s near the ocean but also just a stone’s throw away from shops, restaurants, and local cultural stops. The location is breathtaking and the house itself has a private balcony where you can see the moon unhindered, especially when it’s full. What about the “beer,” you ask? Well, Florida Keys Brewing Co. tasting room is located downstairs. You definitely would want to spend time there as well. This Airbnb in Islamorada is pet-friendly too!

Stayed at this property?
Islamorada, Florida, United States
48.92 km (30.4 mi) from Everglades National Park
173 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the bathroom has hidden heater for your bathing comfort
we had a front row seat from the comfortable balcony
it was decorated with comfortable cozy furniture and the bed was so comfortable
the a/c felt amazing after a long hot day of fishing
the beds were so comfy as well
Cleanliness:
so clean and comfy
it was so clean and neat
the apartment is clean and easy
the apt is spacious clean and well appointed
the apartment was so spacious and spotlessly clean on arrival
Host:
the host was super friendly and accommodating
florida brewery downstairs and the staff were awesome
our hosts were very nice and accomodating
she is very attentive and easy to reach
all in all a wonderful host with a wonderful home hopefully be back soon
Location:
great place central to everything
great location better than we expected
beautiful space and central to everything on islamorada
we were able to walk to great restaurants and shopping
best location in islamorada close walk to restaurants breweries and markets
Read more reviews

10. The Marbella Villa (from USD 1104)

Best for: Luxury travelers, pet parents, families with kids and infants, nature lovers, group stays

Look no further if you want the most extravagant getaway in Islamorada. Book a stay at The Marbella Villa, which has a modern interior and furnishings and is ideal for large groups as it offers spacious bedrooms with premium beds. The villa has an open-concept floor plan connecting the fully equipped kitchen, dining area, and living room. The property also has a large covered lanai where guests can enjoy the fresh breeze coming from the waterfront.

Stayed at this property?
Islamorada, Florida, United States
49.41 km (30.7 mi) from Everglades National Park
13 reviews   Wifi Available
Entire villa 7 Beds 12 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
beautiful sunsets and more than enough room for all of us
this beautiful house sits in a resort there is a pool and ocean views
Host:
the resort staff was great and accommodated every need
the front desk staff is very sweet and attentive to your needs
Location:
it is a perfect location for a large group to vacation
Read more reviews

11. The Butterfly House (from USD 1150)

Best for: Beach lovers, luxury travelers, pet parents, families with kids and infants, group stays

Dive right into the ocean or walk along the beach upon waking up when you stay at The Butterfly House. This rental features a fully furnished interior with essentials, including a full kitchen with a gas stove and dishwasher. Moreover, the property features an outdoor shower to ensure an easy after-swim rinse. Additionally, guests can enjoy private access to an outdoor swimming pool. Fur parents may bring their pets inside the premises too!

Stayed at this property?
Islamorada, Florida, United States
48.72 km (30.3 mi) from Everglades National Park
28 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 7 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
the outdoor space was so peaceful and the pool and outdoor games made it fun for the kids
we loved the waterfall showers and extra amenities
Cleanliness:
the house itself was cozy clean & had everything we needed
the inside of the house was really clean and well cared for
Host:
the hosts were responsive and accommodating
lovely host home and property
our host lisa was very friendly & helpful
lisa was very accommodating and responsive
Location:
it is conveniently located near many good restaurants and shops
great location lots to do & a lot of restaurants to choose from nearby
the butterfly house is an absolutely stunning location the dock pool hot tub- amazing
Read more reviews

12. Lazy Daze Beach House (from USD 277)

Best for: Families with kids, group stays, beach lovers

Lazy Daze Beach House is a family-friendly accommodation with plenty of sleeping amenities, including a king bed, two double beds, and two single beds. Besides that, the rental has air conditioning and WiFi. The property also has laundry appliances, which are helpful for extended stays. After enjoying the beach, guests can relax further by swimming in the on-site pool. You may even sunbathe on the poolside with lounge chairs.

If you’re arriving by car, note that free parking is available on the premises.

Stayed at this property?
Islamorada, Florida, United States
49.35 km (30.7 mi) from Everglades National Park
23 reviews   Superhost Wifi Available
Entire townhouse 5 Beds 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
the kids loved the tide pools and the pool
the townhouse was really great updated kitchen and bathrooms and we loved the view while relaxing on the balconies
Cleanliness:
the house was clean and well supplied
we had a great time condo was clean modern and had every amenity we could have asked for
the house was clean beautiful and had an amazing view
Host:
host lauri very kind and very prompt replying to any questions
a dream place with perfect hosts very attentive and non-invasive
cannot beat the weather laurie and randy were attentative to our needs and great hosts
lauri and randy were super helpful and responsive
Location:
very close to great food and shopping
wonderful location in a quiet area
it was a perfect location for our first visit to the keys
an ideal place to rest with the family or for a romantic getaway
great location with plenty of bed space for a two bedroom
Read more reviews

13. Fully furnished home with ocean views (from USD 1397)

Best for: Beach lovers, families with infants, group stays

Experience a serene vacation by renting this fully furnished home with ocean views. It lies directly on the oceanfront, allowing guests to access the beach anytime. The rental provides guests with modern conveniences for a more entertaining stay, including a flat-screen TV in the living room. Moreover, this home has a spacious balcony, perfect for savoring the ocean breeze.

Note that the pool is accessible to all guests renting this home. The property also has a private entrance to ensure safety and privacy.

Stayed at this property?
Islamorada, Florida, United States
50.4 km (31.4 mi) from Everglades National Park
12 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
Cleanliness:
the property has a totally modernised interior is spotlessly clean and enjoys its own private beach and jetty
Read more reviews

14. Lovely refurbished home with a back porch (from USD 420)

Best for: Families, group stays, beach lovers

Take advantage of this lovely refurbished home situated right next to the ocean. It features a spacious, well-designed kitchen and living room with floor-to-ceiling glass doors and expansive windows, offering guests a panoramic ocean view. The property also boasts a large back porch and yard. Free parking is even available.

You can find this home in a secluded area, yet it is close to downtown Islamorada, allowing you to conveniently reach essential establishments, such as shopping spots and grocery stores.

Stayed at this property?
Islamorada, Florida, United States
50.19 km (31.2 mi) from Everglades National Park
15 reviews   Wifi Available
ENTIRE HOME 3 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
two large bedrooms with en-suite bathroom fully equipped kitchen nice balcony and even a grill
the house is newly renovated (post-irma) and has plenty of room and all the comforts of home
Cleanliness:
it was very clean when we arrived
the place was well maintained and clean
this place is perfect clean well-appointed and nicely updated
place had everything we needed and was very clean
lovely home perfect layout clean decor and the view is unmatched
Location:
it’s a great location and the house has everything you could ever need
views are amazing and location is convenient to everything you could need while on vacation
it’s a community that we love and hold close to our heart
Read more reviews

15. Charming home near a fishing pier (from USD 8873)

Best for: Outdoor enthusiasts, families with kids and infants, beach lovers, group stays

Start each day with a calming view by renting this charming oceanfront home. This rental is the best choice for those traveling as a large group as it offers several spacious bedrooms and bathrooms equipped with sleeping and bath essentials. Moreover, the property features an outdoor shower to make it easier for guests to rinse after swimming at the beach or in the private saltwater pool.

If you’re into fishing, enjoy easy access to the fishing pier from this rental.

Stayed at this property?
Tavernier, Florida, United States
49.22 km (30.6 mi) from Everglades National Park
10 reviews   Superhost Wifi Available
ENTIRE HOME 13 Beds 14 Guests 5 Bedrooms 5 Bathrooms

Accommodates: 14

Top guest reviews
Host:
we had a fabulous time bobby is a great super helpful and responsive host
Read more reviews

16. Modern villa at La Jolla Resort (from USD 7410)

Best for: Families with infants, beach lovers, group stays

Experience the grandeur of staying in a modern villa by staying at La Jolla Resort. The resort offers an elegantly designed villa with contemporary furnishings and top-notch amenities, including a fully equipped kitchen with a stainless steel oven and a Keurig coffee machine. If you want to cook a more intimate meal, you can use barbecue utensils, which include a grill, charcoal, and bamboo skewers.

The property also provides guests with open-air settings, including fire pits and private outdoor seating.

Stayed at this property?
Islamorada, Florida, United States
48.67 km (30.3 mi) from Everglades National Park
40 reviews   Wifi Available
ENTIRE HOME 5 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Cleanliness:
clean and stylish interior
house was clean comfortable and had everything we needed
Host:
staff were very nice and were helpful
Location:
great location close to everything
Read more reviews

17. Bright and airy house for eight (from USD 449)

Best for: Families with kids and infants, group stays, outdoor enthusiasts

This eight-person house has all the amenities you’d want from a home away from home. Each of the property’s three bedrooms has a bathroom, so everyone can sleep well and feel fresh all day. You can spend your time watching TV while relaxing on the plush couch in the living area.

However, it’s the outdoor features that really shine in this property. On one end of the house is a mini putting green, and right beside it is the boat dock. The pool is perfect for the summer months, though you can have it heated during cooler months for an extra charge of 15 USD a day.

Stayed at this property?
Islamorada, Florida, United States
50.93 km (31.7 mi) from Everglades National Park
57 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the house is very comfortable and the peekaboo ocean view is fantastic
the pool is great with afternoon shade which was great after a day in the sun
Cleanliness:
the house was very clean and well maintained
clean fresh and great communication with the owner
a++++ minutes from the ocean by boat lots of tarpons in backyard clean spacious quiet
the home is stylishly decorated very clean great kitchen and plenty of space
Host:
the host was extremely quick to respond and help us with whatever we needed
we loved this home in islamorada it is beautifully decorated and very clean the host provided most essentials
Location:
house is in excellent condition location is fairly private
great location on and off the water
the location of the house is perfect for getting to various local restaurants and marinas
beautiful home at a great location area was secluded and quiet
we had a great week at jaime & mike’s place super convenient to the oceanside bayside and local marina
Read more reviews

18. Beautiful bayside estate with a pool (from USD 4867)

Best for: Pet parents, families with kids and infants. group stays, beach lovers

Treat your loved ones to an unforgettable trip to this beautiful bayside estate on the south of Robbie’s Marina. Coconut trees surround the estate, making it perfect for all nature enthusiasts. Besides a private beach, guests can enjoy a relaxing outdoor pool with beach chairs for sunbathing. Extend your daily exercise at the on-site gym with high-quality workout equipment.

If you’re a fur parent, you’ll also appreciate your pets being welcome inside the premises. So, don’t hesitate to bring them along.

Stayed at this property?
Islamorada, Florida, United States
50.01 km (31.1 mi) from Everglades National Park
6 reviews   Superhost Wifi Available
ENTIRE HOME 7 Beds 12 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 12

Top guest reviews
Host:
sean and the house management team were very helpful throughout our stay
Location:
very beautiful place in great location with lots of boating and activities for kids
Read more reviews

19. Oceanfront villa with saltwater pool (from USD 1181)

Best for: Beach lovers, pet parents, families with kids and infants, group stays

Let yourself in on the expansive views at this oceanfront villa. With access to a private beach, this property allows you to enjoy spectacular sunrises over the dunes in peace. Guests are invited for a dive in the private, saltwater pool, which can be heated on prior request. The property features a private patio, a fully fenced private back garden and an outdoor dining area with a barbecue grill.

While parties are not allowed, guests can still indulge in a laid-back, alfresco dinner. Furry friends are welcome for an additional fee. A monthly discount and cleaning fee apply.

Stayed at this property?
Islamorada, Florida, United States
50.55 km (31.5 mi) from Everglades National Park
49 reviews   Superhost Wifi Available
Entire villa 9 Beds 16 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
Host:
and an excellent service and attention from the host
Location:
beautiful house in great location it has everything you need
the pool is the one perfect place to spend in the house after your time on the beach
Read more reviews

20. Charming house with a large covered terrace (from USD 437)

Best for: Families with kids, pet parents, group stays

Decked out in pastel blue and white hues, the cottage is reminiscent of the island’s pristine shores. It has a washer and dryer, so there’s no need to worry about your laundry. There’s also a well-equipped kitchen for self-catering, and you can enjoy your meals in the outdoor dining area.

The outdoor pool is the perfect spot to cool off on a warm day, while the large covered terrace upstairs is great for relaxing in the evening as the sun goes down.

Stayed at this property?
Islamorada, Florida, United States
50.24 km (31.3 mi) from Everglades National Park
22 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Cleanliness:
a nice fish cleaning table and fresh water on the dock for easy clean up
the house was just as described and was very clean on arrival
very clean great location and communicative host
Host:
we highly recommend this home as adriana was an amazing host and the home is well cared for
left the owner just a few tips to make future visits that much better
the neighborhood was quiet welcoming friendly & safe
Location:
place is well worth it beautiful home and great location
great spot in a great location sweet little private beach within walking distance was icing on the cake
the house and location are hard to beat very nicely decorated and furnished
a great place to vacation
Read more reviews

21. Blue Dolphin (from USD 1050)

Best for: Families with kids and infants, beach lovers, pet parents, group stays

Enjoy a comfortable stay inside Blue Dolphin, a lovely home for large groups. It features a spacious layout with a modern kitchen and an outdoor Weber grill, allowing guests to prepare food without hassle. Besides essential home amenities, the property has relaxing facilities, including a saltwater pool and a sandy backyard.

Guests can also make their stay more entertaining by playing table tennis near the pool. Moreover, the property has an observation pier for a more convenient swimming and snorkeling experience.

Stayed at this property?
Islamorada, Florida, United States
49.44 km (30.8 mi) from Everglades National Park
4 reviews   Wifi Available
ENTIRE HOME 6 Beds 10 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 10

Top guest reviews
Cleanliness:
huge home perfectly clean great layout and so much privacy
Read more reviews

22. The Russell Estate (from USD 19915)

Best for: Beach lovers, families kids and infants, group stays

This holiday retreat sits within a premium property that faces the ocean and boasts plenty of white sand. The outdoor pool with sun loungers is the best spot to enjoy unobstructed view of this scenery. The pool itself is a relaxing spot to take a dip during the hotter days.

Inside the home, you’ll find a wide selection of modern comforts, including a full kitchen, TVs, and even a small workspace, to name a few. The three bedrooms are more than enough for six guests to have a good night’s sleep.

Stayed at this property?
Islamorada, Florida, United States
48.47 km (30.2 mi) from Everglades National Park
31 reviews   Wifi Available
ENTIRE HOME 4 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Cleanliness:
the house is very cozy comfortable and clean
Host:
denira and alex were amazing hosts
thanks for being a host and creating lifetime memories for our family
check in was easy and the owner provided some much appreciated flexibility on check out
the long dock was a great lookout for all kinds of fish
he was responsive to texts and very helpful
Location:
location was so perfect and convenient
good location and great hosts
the perfect place to spend time on the best florida key
this is a wonderful place to stay and isla morada is beautiful
if you're looking to relax this is the place to be
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23. Cozy rental with a patio (from USD 2205)

Best for: Families, beach lovers, couples

Book a stay in this cozy rental if you want a budget-friendly getaway in Islamorada. It is a family-friendly rental with a queen bed and an air mattress in the common area. The rental also has air conditioning and free WiFi. You can even find laundry appliances on the premises. The property covers a private beach, yard, and dock, which guests can enjoy without limits.

To experience the vibe outside, stay on the patio with comfortable outdoor seating and a Weber grill for barbecue nights.

Stayed at this property?
Islamorada, Florida, United States
50.32 km (31.3 mi) from Everglades National Park
44 reviews   Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
fantastic views comfortable accommodations private little spot
the garden villa was very clean and well stocked with kitchen and household supplies including a washer/dryer
1st of all the bed is comfortable
Cleanliness:
very clean nicely decorated
we had a really nice clean bbq in our patio
clean comfortable apartment in a great location
Host:
the owners gave us a tour which was really special
a1a is beyond helpful & so nice
Location:
the location and proximity to all the restaurants is the best
this place is perfect the property is magnificent
great location good local feel nice people
great place for adult get away or famillies
great place easy access to everything can’t wait to book again next year
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24. Charming home with beach access (from USD 14379)

Best for: Nature lovers, pet parents, beach lovers, families with kids, group stays

Life on the beach can’t get more fun than this! Situated in the neighbourhood of Lower Matecumbe Key, this property offers guests full access to a private beach with canal views. The whitewashed, wood-frame house on stilts will enchant you with its elegance and simplicity. The home also features a private patio, a fire pit and a barbecue grill.

Do note that the property is not suitable for children, but feel free to bring along your furry friends for a cosy gathering. Offers for month-long stays are available, and a cleaning fee applies.

Stayed at this property?
Islamorada, Florida, United States
50.48 km (31.4 mi) from Everglades National Park
30 reviews   Superhost Wifi Available
ENTIRE HOME 8 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
updated cute kitchen family room w/ great dock space and hot tub
expect a clean and comfortable place to relax with all the amenities you have at your house
beds were comfortable (very soft sheets) and the bunk room was perfect for the kids
Cleanliness:
kitchen has everything bathroom's are updated and clean
the house was clean well-stocked and the kitchen/living room space was wonderful for hanging out
house is lovely well maintained and clean
Host:
this place is fantastic hosts are awesome
kate was very responsive to our questions and needs
kate was very responsive and answered any questions at any time of the day or night
amazing location and house kate was a great host and was very responsive
kate was very responsive and helpful providing tips before i even thought i needed them
Location:
great location with restaurants close by and we made memories to last a lifetime
overall a great location and beautiful home
nice location comfortable beds nice dock for fishing boat
kate’s place is in a wonderful location
amazing location right on the canal and a quick 2 minute drive to their private beach
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25. Comfy lair with an ocean view

Best for: Beach lovers, outdoor enthusiasts, couples

Superhost Angie offers this apartment to couples who require a great ocean view from the front door. This Islamorada vacation rental has a private patio and all the necessities you require for a comfortable and romantic weekend at Islamorada. You may use the bicycles and kayaks provided. If you’re hungry there’s a barbecue for grilling meats and vegetables. If you feel like fishing, take a boat out with your gear, and maybe you’ll catch a barracuda!

Stayed at this property?
Islamorada, Florida, United States
50.43 km (31.4 mi) from Everglades National Park
642 reviews   Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
lots of space and bed new and comfortable
angie was kind enough to let us borrow her personal fan
however shower tiles looked new and very clean
the property is 100% prime space plenty of room to spread out or be friendly to other guests
the apartment was beautiful and our stay was fantastic
Cleanliness:
space was clean and just as described
angie had it sparkling clean when we arrived
it is clean comfortable and cool
comfortable and clean
the unit was cozy and clean and had everything we needed
Host:
kevin was such a lovely host
kevin was welcoming and helpful
kevin is a great host and very accessible
hosts are very helpful
the host was super friendly and helpful
Location:
absolutely loved the location
beautiful location right on the water
great location very fun kayaking and cool fish and lobsters you can see
perfect location with beautiful private beach
the terrace and the location are the best u can wish for
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26. Secluded studio cottage best for couples

Best for: Couples, beach lovers, watersports lovers, solo travelers

One of the modest and charming stays in Islamorada that’s ideal for couples is Angie’s studio guest suite. This cottage apartment is completely private and secluded and is located close to the gulf. The home may be small, but it features a fully equipped kitchen, a comfortable couch, a queen-sized bed, and a gas grill. A private bathroom is included too. There’s also a private patio with a dining area. If you want to explore the beach, you may borrow kayaks and snorkeling gear for free.

Stayed at this property?
Islamorada, Florida, United States
50.48 km (31.4 mi) from Everglades National Park
427 reviews   Wifi Available
Entire guest suite 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the part we admired most - water-view from the room grill/outdoor eating area
but the view through the sliding door in the main room is great
helpful to travel with a long charging cable/multi port usb plug as outlets as scarce
cottage had everything we needed for a comfortable stay
we loved watching the sunset from the water and having a full kitchen (+grill) available
Cleanliness:
it was very clean and all that we needed
the place is definitely older but very clean and comfortable
cottage is older but clean and well stocked
it has a vintage keys feel; nothing fancy but clean and comfortable
it was clean and spacious with an amazing waterfront view
Host:
kevin is a great host
kevin and dana were great hosts
kevin is a wonderful host
kevin is very friendly
kevin is does everything possible to make his hosts feel comfortable
Location:
quaint amazing location great price
this is a cute place right on the water in a fantastic location
loved our stay perfect location secluded romantic close to all the cool places
lots of good food options close by
this is a nice quiet place conveniently located
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27. Personal space with a private channel

Best for: Families with kids, beach lovers, group stays

A villa that can house five guests who are willing to share three beds and two bedrooms is offered at this property. It is newly remodeled and boasts a fully equipped kitchen. WiFi connection and plenty of entertainment can be found on the premises. But, you should spend more time in the water because you have your own private ocean channel. Who knows what you’ll find out there?

Stayed at this property?
Islamorada, Florida, United States
49.97 km (31.1 mi) from Everglades National Park
208 reviews   Superhost Wifi Available
Entire villa 3 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
there were chairs under some shade to have your breakfast and the pool was nice
the house has a nice fully equipped kitchen and the kids enjoyed the pool
great little villa i little tight with 1 bathroom for 4 "adults"
the heated pool in the little community was also a huge bonus for my kids
darling little cottage with a cute pool/fountain area in a small development
Cleanliness:
everything very clean and well-kept
very clean little house in a tourist heaven
very nicely decorated and clean
brett is a fantastic host and great communication house was clean and comfortable
the house was beautiful and clean the pool was plus too
Host:
brett is a great host and he quickly answered our questions and gave great tips
brett is a great host and has great tips
brett was good host
brett is a great host
brett is a great host he replies fast friendly and very helpful
Location:
awesome location
the location was conveniently close to a variety of fun places
close to great water sport towns
perfect dreamy location on the keys
perfect little cottage with a great location basically right across the street from robbies
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28. Quaint nest for adventurous guests

Best for: Outdoor enthusiasts, beach lovers, couples

A cute, cozy, and exclusive apartment furnished for two is available for a holiday at Islamorada. You will have your own entrance and you can lock up when you feel like heading to a famous sandbar at Whale Harbor Channel. You can reach the local landmark by kayak or jet ski if you are confident in using them, or hire a boat instead.

Stayed at this property?
Islamorada, Florida, United States
50.52 km (31.4 mi) from Everglades National Park
33 reviews  
Entire apartment 1 Bed 1 Bedroom 1 Bathroom

29. Cottage with private beach, kayaks, and coffee

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

A secluded place on the island can be yours if you don’t mind being surrounded by tropical trees. The two-bedroom cottage offers views of the ocean everywhere you turn. When you feel like getting in the water there are three kayaks in the property and they are in great condition. They’re part of the package. If you’re up to the challenge, set out on kayaks to one of the nearby islands, and then race back to the private beach. Superhost Gabriel says the coffee machine comes with Columbian coffee capsules. You’d better make the most of his offers.

Stayed at this property?
Islamorada, Florida, United States
50.77 km (31.6 mi) from Everglades National Park
90 reviews   Superhost Wifi Available
Entire residential home 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the house is beautiful with amazing views from just about all rooms
can’t beat the views the comfort of the master bed or the wonderful treatment you get from gabriel
i loved waking up to see the sea just beyond my bed
Cleanliness:
the house was amazing very clean and well stocked with towels sheets and supplies
the house is absolutely spotless and well furnished and stocked
clean spacious brilliant location
the home was clean and organized
beautiful cottage in islamorada fl clean private and kept up after irma went through
Host:
the host is a genuinely a nice caring person
amd i can vouch that gabriel is an awesome host
gabriel was extremely responsive we didn’t need much as he had everything perfectly ready when we got there
gabriel is a wonderful host
Location:
great house/location and gabriel is so easy to work with
beautiful home in a great location
the location was outstanding and everything was just wonderful
great location the home was right on the water and was conveniently located to local restaurants
a wonderful place right on the beach
Read more reviews

Islamorada - the Village of Islands - is your next holiday destination

The Florida Keys coral archipelago is a vacationer’s delight. Few, if any, leave Islamorada without thinking of going back and most of them return sooner than expected. Islamorada is a perfect manifestation of the region’s heart and soul. Planning a holiday here? Then, book any of the Airbnbs above!

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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Deanna Kathrina, a pediatric physical therapist specializing in neurodevelopmental disability, serves as a teacher and advocate. As a lifelong learner, she enjoys the company of music and aspires...Read more

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