Top 15 Airbnbs In Islamorada, Florida - Updated 2021

airbnb in islamorada

“This village in the Florida Keys, situated between the Gulf of Mexico and the Atlantic Ocean, is the Sportfishing Capital of the World.” If Jeopardy’s Alex Trebek asks this question and your answer is, “What is Islamorada?” then, you’ve hit the jackpot! Islamorada is popular among anglers, sailors, and pirate wannabes. You’ve probably heard about it in the Netflix original series, “Bloodline”, where most of the Rayburns’ dark secrets were revealed. Whether you’ve heard about it or not is of no consequence. What matters is the fact that it’s always a worthwhile spot to visit in the Florida Keys. For starters, the sealife 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 Airbnbs in Islamorada, Florida, below.

1. Three-bedroom home with acres of trees and beach access (from USD 694)

A three-bedroom oceanfront property 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.

3 Bedroom Private Oceanfront House - Sol
25 reviews  Wifi Available
Entire residential home 4 Beds 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8

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

2. Fully equipped cottage in Shady Palms (from USD 196)

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.

2 BR Cozy Cottage at Shady Palms in Islamorada
37 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
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
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
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. Personal space with a private channel (from USD 179)

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?

The Island Dog Conch House 2 Bedoom Islamorada FL
Islamorada, Florida, United States
151 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
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
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
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
Read more reviews

4. Villa close to nightlife (from USD 235)

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.

Bayside Villa in Islamorada
Islamorada, Florida, United States
12 reviews Superhost  Wifi Available
Entire villa 1 Bed 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
lloyd is a kind and responsive host
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

5. Upscale villa with private beach and pool (from USD 299)

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.

End of Summer at Anglers Reef Paradise
Islamorada, Florida, United States
19 reviews Superhost  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
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
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
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

6. Relaxing house all to yourself and with downstairs access to a tasting room (from USD 150)

According to Cheryl, your Superhost, Flakeys 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!

Islamorada, Florida, United States
112 reviews Superhost  Wifi Available
Entire residential 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
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
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
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

7. Cool and comfortable studio cottage (from USD 165)

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.

Cottage - Waterview, Kayak, Snorkel
Islamorada, Florida, United States
366 reviews Superhost  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
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
kevin is a wonderful host
kevin and dana were great hosts
kevin is a great host
kevin is does everything possible to make his hosts feel comfortable
kevin is very friendly
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
Read more reviews

8. Apartment with stunning bay views (from USD 219)

Charlie and Terry host this bright and homey apartment in Islamorada. Built with one bedroom, the Airbnb is ideal for four guests and is surrounded by the beauty of nature, wildlife, and water views. The home comes with free Wi-Fi, a TV with Netflix, a fully functional and spacious kitchen, as well as a modest living room. Outside there is a patio with a seating area and a hammock where you can lounge and enjoy the sea breeze. In the summer, some of the popular activities nearby include fishing and lobstering.

Endless Bay Views, Sues Promise Islamorada FL
Islamorada, Florida, United States
21 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
very clean nicely decorated
we had a really nice clean bbq in our patio
clean comfortable apartment in a great location
the owners gave us a tour which was really special
a1a is beyond helpful & so nice
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
Read more reviews

9. Comfy lair with an ocean view (from USD 138)

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!

Efficiency - Snorkel, Swim, Kayak
Islamorada, Florida, United States
552 reviews Superhost  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
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
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
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
Read more reviews

10. Townhouse with front seats to gulf sunsets (from USD 148)

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 property has a concrete 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.

Ocean Islamorada BeachHouse POOL!70' DOCK boatrent
Islamorada, Florida, United States
13 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
fantastic location large apartment with all we needed clean modern i recommend it
and it was all possible with the help of walter our host
he was so helpful and his place is great
wonderful place in a great location
we had an amazing vacation at walter's place
Read more reviews
Monthly discount: 21% off

11. Luxurious sanctuary with access to dolphins (from USD 265)

This gorgeous vacation rental 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.

NEW Secret Keys Waterfront Hideout has EVERYTHING!
Islamorada, Florida, United States
206 reviews Superhost  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
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
our hosts were perfect
great hosts that are very helpful with quick responses
the hosts were very helpful in getting us settled in
hosts were responsive and accommodating
the hosts were readily available and respected our privacy
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

12. Quaint cottage on the ocean (from USD 135)

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.

Ocean Front Cottage
Islamorada, Florida, United States
3 reviews Superhost  Wifi Available
Entire cottage 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

13. Cottage with private beach, kayaks, and coffee (from USD 395)

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.

Oceanfront, Private Beach, Beach Cottage w/Kayaks
Islamorada, Florida, United States
85 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
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
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
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

14. Bayside townhouse with sunset balcony and marina (from USD 220)

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.

Waterfront Townhouse in Islamorada with Boat Slip
Islamorada, Florida, United States
50 reviews Superhost  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
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
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
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

15. Quaint nest for adventurous guests

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.

Beach Front Private Apartment with Kayak and Bikes
Islamorada, Florida, United States
33 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom

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? If you don’t know where to stay, Islamorada offers plenty of Vrbos and other vacation rentals, including these amazing Airbnbs.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Deanna is a pediatric physical therapist from the Philippines who's been writing online content since 2012.

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