“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.
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
Top guest reviewsRead more reviewsgreat location and roomy accommodations for our groupwonderful location beautiful scenery and great service
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
Top guest reviewsoverall the cottage was very comfortable (especially the beds) and we would definitely come backthe cottage is tiny but comfortable for a family of fourcozy cottage is the perfect name - it was cozy and quaintpool was beautiful and had a much fun with our neighborsand the pool is perfect to take a dipthis is a clean cozy cottageit was updated clean and well appointedthe villa was very clean and comfortablea great little clean and stylish space with easy access to a nice clean poola very clean homey well equipped small home
Host:we enjoyed meeting a few of the owners who shared restaurant tips with uswe had everything we needed and the host was very responsivethe host was responsive to messages and the check-in and check-our process was easy and smoothwe enjoyed meeting the friendly neighborscarol was reaponsive friendly and helpfulRead more reviewsnice location and cute housegreat location and very privatecute place and very convenientgreat location for us would come back againstill a good location for the price point though
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 FLIslamorada, Florida, United StatesSuperhost
Top guest reviewsthere were chairs under some shade to have your breakfast and the pool was nicethe house has a nice fully equipped kitchen and the kids enjoyed the poolgreat 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 kidsdarling little cottage with a cute pool/fountain area in a small developmenteverything very clean and well-keptvery clean little house in a tourist heavenvery nicely decorated and cleanbrett is a fantastic host and great communication house was clean and comfortablethe 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 tipsbrett is a great host and has great tipsbrett was good hostbrett is a great hostbrett is a great host he replies fast friendly and very helpfulRead more reviewsawesome locationthe location was conveniently close to a variety of fun placesclose to great water sport townsperfect dreamy location on the keysperfect little cottage with a great location basically right across the street from robbies
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 IslamoradaIslamorada, Florida, United StatesSuperhost
Top guest reviewsthe bed was comfortable too they have all the kitchen supplies you’d need
Host:lloyd is a kind and responsive hostRead more reviewsgood house great location in townit's a great place to staygreat location very clean nice to meet other's staying in the area
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 ParadiseIslamorada, Florida, United StatesSuperhost
Top guest reviewsnice heated pool and beach area for those staying in the communityhouse was very clean modern and decorated beautifullythe house was very cleanher place was gorgeous clean and comfortablethis place is great super clean and spaciousthis is an excellent place to stay very clean the gated community was well maintained
Host:gina is absolutely a super hostgina is an awesome very personable hostgina was very responsive to any questions and a few small things that arosegina was very quick to respond to our inquiries and was an excellent hosta great and attentive host nicely and comfortably furnished houseRead more reviewsgreat location and communitywe loved the location and the house was beautiful it has everything you need so just bring your clothesthe location is great for seeing all the keys have to offermany places nearby with great musica great place to stay
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!
Flakey'sIslamorada, Florida, United StatesSuperhost
Top guest reviewsthe bathroom has hidden heater for your bathing comfortwe had a front row seat from the comfortable balconyit was decorated with comfortable cozy furniture and the bed was so comfortablethe a/c felt amazing after a long hot day of fishingthe beds were so comfy as wellso clean and comfyit was so clean and neatthe apartment is clean and easythe apt is spacious clean and well appointedthe apartment was so spacious and spotlessly clean on arrival
Host:the host was super friendly and accommodatingflorida brewery downstairs and the staff were awesomeour hosts were very nice and accomodatingshe is very attentive and easy to reachall in all a wonderful host with a wonderful home hopefully be back soonRead more reviewsgreat place central to everythinggreat location better than we expectedbeautiful space and central to everything on islamoradawe were able to walk to great restaurants and shoppingbest location in islamorada close walk to restaurants breweries and markets
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, SnorkelIslamorada, Florida, United StatesSuperhost
Top guest reviewsthe part we admired most - water-view from the room grill/outdoor eating areabut the view through the sliding door in the main room is greathelpful to travel with a long charging cable/multi port usb plug as outlets as scarcecottage had everything we needed for a comfortable staywe loved watching the sunset from the water and having a full kitchen (+grill) availableit was very clean and all that we neededthe place is definitely older but very clean and comfortablecottage is older but clean and well stockedit has a vintage keys feel; nothing fancy but clean and comfortableit was clean and spacious with an amazing waterfront view
Host:kevin is a wonderful hostkevin and dana were great hostskevin is a great hostkevin is does everything possible to make his hosts feel comfortablekevin is very friendlyRead more reviewsquaint amazing location great pricethis is a cute place right on the water in a fantastic locationloved our stay perfect location secluded romantic close to all the cool placeslots of good food options close bythis is a nice quiet place conveniently located
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 FLIslamorada, Florida, United States
Top guest reviewsfantastic views comfortable accommodations private little spotthe garden villa was very clean and well stocked with kitchen and household supplies including a washer/dryer1st of all the bed is comfortablevery clean nicely decoratedwe had a really nice clean bbq in our patioclean comfortable apartment in a great location
Host:the owners gave us a tour which was really speciala1a is beyond helpful & so niceRead more reviewsthe location and proximity to all the restaurants is the bestthis place is perfect the property is magnificentgreat location good local feel nice peoplegreat place for adult get away or familliesgreat place easy access to everything can’t wait to book again next year
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, KayakIslamorada, Florida, United StatesSuperhost
Top guest reviewslots of space and bed new and comfortableangie was kind enough to let us borrow her personal fanhowever shower tiles looked new and very cleanthe property is 100% prime space plenty of room to spread out or be friendly to other gueststhe apartment was beautiful and our stay was fantasticspace was clean and just as describedangie had it sparkling clean when we arrivedit is clean comfortable and coolcomfortable and cleanthe unit was cozy and clean and had everything we needed
Host:kevin was such a lovely hostkevin was welcoming and helpfulkevin is a great host and very accessiblehosts are very helpfulthe host was super friendly and helpfulRead more reviewsabsolutely loved the locationbeautiful location right on the watergreat location very fun kayaking and cool fish and lobsters you can seeperfect location with beautiful private beachthe terrace and the location are the best u can wish for
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 boatrentIslamorada, Florida, United StatesSuperhost
Top guest reviewsthe condo is very well stocked with towels and the kitchen is a full array of suppliesfantastic location large apartment with all we needed clean modern i recommend it
Host:and it was all possible with the help of walter our hosthe was so helpful and his place is greatRead more reviewswonderful place in a great locationwe had an amazing vacation at walter's placeMonthly discount: 21% off
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 StatesSuperhost
Top guest reviewsbeautifully decorated room with good amenitiesfan tables lounges and hammocks) hanging over the waterwe appreciated all of the extras in the apartment and of course the tiki hutvery cozy little place with a perfect king size bed you will love to sleep ingreat stay exceptionally clean and loved the tiki hutthe room was sparkling cleanthe space is spotless with many thoughtful touchessoooo relaxing the unit was super clean and stocked with lots of thoughtful itemsroom was clean all amenities worked well bed was just
Host:our hosts were perfectgreat hosts that are very helpful with quick responsesthe hosts were very helpful in getting us settled inhosts were responsive and accommodatingthe hosts were readily available and respected our privacyRead more reviewsperfect for couples or close friendsthe location was breathtaking and very privatewe enjoyed the restaurants close by alsothe location was great and easy to findgreat location halfway between key largo and key west
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 CottageIslamorada, Florida, United StatesSuperhost
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/KayaksIslamorada, Florida, United StatesSuperhost
Top guest reviewsthe house is beautiful with amazing views from just about all roomscan’t beat the views the comfort of the master bed or the wonderful treatment you get from gabrieli loved waking up to see the sea just beyond my bedthe house was amazing very clean and well stocked with towels sheets and suppliesthe house is absolutely spotless and well furnished and stockedclean spacious brilliant locationthe home was clean and organizedbeautiful cottage in islamorada fl clean private and kept up after irma went through
Host:the host is a genuinely a nice caring personamd i can vouch that gabriel is an awesome hostgabriel was extremely responsive we didn’t need much as he had everything perfectly ready when we got theregabriel is a wonderful hostRead more reviewsgreat house/location and gabriel is so easy to work withbeautiful home in a great locationthe location was outstanding and everything was just wonderfulgreat location the home was right on the water and was conveniently located to local restaurantsa wonderful place right on the beach
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 SlipIslamorada, Florida, United StatesSuperhost
Top guest reviewsalso the pool is huge heated and with plenty of lounge chairsvery clean space beautiful townhomethe place was very clean and nicely decoratedthe condo was very clean spacious and well stockedthe townhouse was extremely clean and comfortablethe pool was beautiful clean and refreshing
Host:claire was a wonderful host and she has a lovely homeclaire is a wonderful host that exceeded expectationsclaire is a very good host and answered very quick when i had questionsclaire was an amazing host that was quick to respond and clarify any questions i hadhighly recommend this rental and this hostRead more reviewsthe location is perfectnice townhome with great locationgreat central location in the keysso close to our new favorite restaurantsthe location of claire’s place was perfect
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 BikesIslamorada, Florida, United States
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.
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