Airbnb private accommoation vacation rentals US > South Florida > Islamorada

Top 10 Airbnbs In Islamorada, Florida

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-wanna-be’s. 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 hurricanes events in The Florida Keys History and Discovery Center. While you are charting your itinerary, you must also prioritize finding a place to stay. Read about the top Airbnbs in Islamorada, Florida.

1. Luxurious sanctuary with access to dolphins (from USD 99)

This gorgeous property 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. It 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!
36 reviews
Entire house 1 Bed 2 Guests

2. 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. It 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
Entire guest suite 1 Bed 1 Bedroom 1 Bathroom

3. Quaint nest for adventurous guests (from USD 135)

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

4. Personal space with a private channel (from USD 135)

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
63 reviews
Entire villa 3 Beds 2 Bedrooms 1 Bathroom
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

5. Townhouse with front seats to gulf sunsets (from USD 130)

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 wavail Boat & 70' DOCK
Islamorada, Florida, United States
8 reviews
Entire townhouse 3 Beds 2 Bedrooms 1 Bathroom

6. Cottage with private beach, kayaks, and coffee (from USD 375)

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
44 reviews
Entire house 3 Beds 2 Bedrooms 2 Bathrooms
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

7. Relaxing house all to yourself and with downstairs access to a tasting room (from USD 225)

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.

Islamorada, Florida, United States
72 reviews
Entire house 3 Beds 2 Bedrooms 1 Bathroom
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

8. Bayside townhouse with sunset balcony and marina (from USD 210)

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.

Beautiful Waterfront Townhouse in Islamorada
Islamorada, Florida, United States
23 reviews
Entire townhouse 4 Beds 2 Bedrooms 2 Bathrooms

9. Upscale villa with private beach and pool (from USD 225)

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.

Fall Discounts in Paradise
Islamorada, Florida, United States
15 reviews
Entire villa 4 Beds 2 Bedrooms 2 Bathrooms

10. Three-bedroom home with acres of trees and beach access (from USD 500)

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
Islamorada, Florida, United States
16 reviews
Entire house 4 Beds 3 Bedrooms 3 Bathrooms
Top guest reviews
great location and roomy accommodations for our group
wonderful location beautiful scenery and great service
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. If you must plan for a holiday there, bring your head down from clouds in the meantime. Book a place to stay in any of these excellent Airbnb lodgings in Islamorada.

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A pediatric physical therapist for children with neurodevelopmental disability. Lives by words, music and the sustaining beauty of a world she continues to explore.

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