Beach house holiday rentals in Islamorada

Find and book unique beach houses on Airbnb

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Popular amenities for Islamorada beach house rentals

Beachfront house rentals

Superhost
Home in Marathon
4.85 out of 5 average rating, 26 reviews

(#8)Waterfront 4 Bed 3 Bath Pool Home w Free Dock

MollyRating, 5 stars2 months ago
We had a delightful time. The unit was clean & comfortable and easily accommodated our party of 5 adults. The balcony was very pleasant and had a great relaxing view. The shared beach was also very relaxing with plenty of chairs and a nice covered card table area. This is in addition to the multiple seating options at our private pool. Families were enjoying the provided kayaks of which there were plenty. Susan and Dale were extremely responsive to all of our inquiries including showing up to address an issue within 15 minutes! Overall we had a very pleasant stay.
Top Guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 122 reviews

Paradise found!Key Colony Beach,Cabana Club.

NathanRating, 5 stars2 days ago
We had a great time at Paradise Found. The property was lovely and clean, all very well maintained. The location was beautiful, backing onto the water and enormously peaceful, a great setting. Kari was very communicative and always responded quickly to any queries. Overall, we were very happy.
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 63 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

BarbaraRating, 5 stars1 week ago
You won’t find a better set up than this with family. Playground, beach, pool , sidewalks for walking everywhere, and great kayaking area as well. And the owner makes sure his guests have all they need.
Superhost
Home in Key Colony Beach
5 out of 5 average rating, 3 reviews

The Sandcastle - 2bed/1bath half duplex with docka

RachelRating, 5 stars11 months ago
Key Colony Beach is a quaint little village in and of itself. This duplex was exactly as the pictures show. Beds, pillows and sofa very comfortable. The kitchen was the most well stocked of all we’ve stayed in; all cooking, baking, and dining that you have at home and then some. Towels and linens were plentiful and clean. The neighbors were also kind and courteous. Having the boat dock was a big plus as we brought our boat with us. We put-in and pulled-out at the public landing across the street from the entrance, for a $25 fee each occurrence . Short, beautiful ride to our dock. Docking was easy and included an outside cleaning station and shower. Nice outdoor seating and Palms. The retractable awning above the sliding glass door was also perfect for blocking some of the afternoon sun. The location is convenient to dining, grocery and convenience stores. We loved everything about our vacay, other than having to leave. We’ll definitely be back.
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars3 months ago
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.
Guest favourite
Home in Marathon
4.9 out of 5 average rating, 31 reviews

Viamarhe House-Private beach, Kayak, yard games

JasonRating, 5 stars3 weeks ago
Everything about this home is as described in the listing. Host is very responsive and friendly. We completely loved being there and it was incredibly peaceful and relaxing. We would love to come back again. Having the ocean for a back yard was awesome! This was probably my favorite AirBnB stay ever! We did not want to leave.
Superhost
Home in Key Largo
4.91 out of 5 average rating, 100 reviews

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach

KrystalynRating, 5 stars1 month ago
Fantastic stay ! Martha was a great host, very responsive and her house is beautiful and more than accommodating. The duplex is in a gated community with a beach, pool, and tennis court ! The weather was not the best so the beach wasn’t the best hang out but 10/10
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 6 reviews

Key Colony Beach Waterfront 321

JeanneRating, 5 stars8 months ago
Great place right in the heart of Key Colony. House had all we needed and more to make our 8 day stay comfortable. Great boat dock with plenty of room for 2 31 ft boats.

Beach house rentals with a pool

Top Guest favourite
Home in Marathon
5 out of 5 average rating, 38 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

AmyRating, 5 stars3 months ago
We have enjoyed our time! The pool was excellent and the back yard very private, which was wonderful! Close walk to the beach and near walking paths. Had to drive to restaurants, but plenty of options w/in 10 min. Living space great, beds comfy. Floaties and kayaks in the garage, we used both. Caught some fish off the back canal, we even ate some! Would stay here again!
Superhost
Home in Marathon
5 out of 5 average rating, 7 reviews

Delightful Canal Front Pool Home! Direct to Ocean!

SydneyRating, 5 stars3 months ago
This home offers so many amenities!! We thoroughly enjoyed biking, kayaking, the heated pool, grilling, and several games the host had for us. The large kitchen made it easy for our group of 6 to interact and enjoy meals together. The host was very responsive with any questions we had and checked in throughout the stay to ensure our needs were being met. This was our second year staying in Marathon, would stay at this location again.
Guest favourite
Home in Marathon
4.94 out of 5 average rating, 16 reviews

Pool & Spa, Walk to Beach, Dock, Tiki, Lux Home

Stefan And KarenRating, 5 stars5 days ago
The house was spacious and clean, and we got good use out of the pool and hot tub. Bert requires signing a separate contract after booking on AirBnB, but worked with us to tailor the language. Towels are provided but be prepared to bring most other amenities like shampoo, etc yourself. Also, be aware that Sunrise Drive is a private road and you cannot access the beach there - Sombrero Beach is about a 15 minute walk, but definitely worth the walk!
Superhost
Home in Marathon
4.79 out of 5 average rating, 34 reviews

Luxury Waterfront Retreat with Dockage & Pool

MindyRating, 5 stars1 month ago
Had an amazing stay at this house with my husband and 4 small kids. The house was spacious and clean, with lots of natural light at soon as the sun came up. The pool was so warm and had a large shallow area that was perfect for our 3 year old. Naomi was a wonderful communicator. It was so sad to have to leave.. Would definitely recommend staying here.
Guest favourite
Home in Key Colony Beach
4.92 out of 5 average rating, 12 reviews

Paradise Cove!30ft Dock Pool BBQ

MelissaRating, 5 stars1 week ago
Had a wonderful stay at Yuni’s. The home was beautiful, well appointed and clean. Yuni was very responsive to all our questions and needs, and super friendly! Thank you Yuni!
Superhost
Home in Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars4 months ago
Stunning location, very comfortable with plenty of space for 10 people. When we arrived we never felt like leaving. Beautiful pool and hot tub surrounded by palm trees, sandy area with great fire pit, gorgeous outdoor eating area and kayaks to drop from pier. Very private location with spectacular sunsets! Fabulous!!!!
Guest favourite
Home in Marathon
4.87 out of 5 average rating, 23 reviews

Golf Coast Oasis

NoraRating, 5 stars2 days ago
We really enjoyed our week at Gulf Coast Oasis! The house was lovely, well-stocked, and great for our family of 5. We very VERY much enjoyed the pool and appreciated being able to heat it. Loved using the bikes and kayaks. Ate on the screened in porch. Madelyn was very helpful and responsive both in advance of and during our trip. Great stay! The only "negative" was the noise from the nearby airport -- not disruptive but worth noting.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 112 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

JessicaRating, 5 stars2 days ago
Our family of 9 loved the house! The pool, corn hole, and roof deck were all huge hits with the kids. The house is perfectly situated on Marathon, close to all the restaurants. Quick drive to Bahia Honda. We will definitely will be back for another visit to Andy’s place.

Private beach house rentals

Guest favourite
Home in Key Largo
4.97 out of 5 average rating, 100 reviews

The Paradise 2

JuliaRating, 5 stars2 weeks ago
We enjoyed our stay at this cute mini home. Our 3 kids loved having their own little space with sleeping arrangements upstairs. Plenty of drawers to store things in! The outdoor area is lovely, we spent a lot of time relaxing out there - and even though it was quite unusually windy during our stay it was still peaceful. We grilled out dinner almost every night. The biggest hit by far was the hammock, every single family member loved lounging in the hammock. We enjoyed the kayaks and fishing off the dock - somehow managed to catch a spiny box puffer (striped burrfish) which was an unexpected surprise! Our kids enjoyed the pool in the community and all of the neighbors we met were very nice. We liked this location, being about 15 minutes from downtown Key Largo it was a great place to stay and a good base from which we took several day trips to nearby beaches & excursions. Lots to do! Luis was very accommodating, appreciated all the quick responses to our questions!
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 47 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

RebeccaRating, 5 stars3 weeks ago
Giselle and Javier were awesome with communication, they gave us a ton of recommendations for food and we tried out almost all of them. Some of the best food we’d ever had and a lot of them were within walking distance of the house! The house was perfect, light, clean, and modern. We were able to catch fish off the dock and even saw a few manatees come through. Probably the best Airbnb we’ve stayed in overall!!
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 58 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

ErinRating, 5 stars2 weeks ago
I can’t say how much we enjoyed this place. So private and clean. Beautiful view. Everything we needed was there. Sad to leave but back to real life. Thank you Thank you!
Top Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 19 reviews

Keys to the Sea + Cabana Club

MarcilleRating, 5 stars2 weeks ago
Our family of 4 really enjoyed our stay! It really was the perfect getaway spot for us to rest and recharge. The amenities available were so convenient, from a well stocked kitchen, bathroom supplies, laundry, a bait freezer, to even having pool towels and a cooler available to use. Our kids ages 11 and 13 spent hours fishing off of the dock out back. We even caught our meal a couple of times! We also really enjoyed access to the Cabana Club! It had a lovely beach front along with a perfect temperature pool! Drinks and food at the club were very reasonable priced. This is our third year in a row visiting the keys and we always enjoy this area. Next year I will be looking at this rental first! Thank you again for the wonderful stay!
Superhost
Home in Marathon
5 out of 5 average rating, 14 reviews

P87 - New Construction house. 4 bedrooms, open wat

KaitlynRating, 5 stars12 months ago
Such a beautiful home in a beautiful location! 2-3 min walk to Sombrero Beach. Safe, walkable neighborhoods, close to loads of great restaurants and activities. Being centrally located in Keys, plenty of options in Marathon or with a short ride north or south. Would definitely recommend/return.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 68 reviews

Private 174ft Dock, Boat Launch, Sombrero Beach

ChrisRating, 5 stars1 month ago
We had a great stay here, beds were comfortable and bathrooms were clean. Kids loved fishing off the dock - although the boat ramp was unavailable, we were able to use the ramp at the marina down the block ($30 each drop). Hosts were easy to communicate with and very helpful when we had a question. Wed definitely stay here again next time in Marathon.
Top Guest favourite
Home in Key Largo
4.89 out of 5 average rating, 122 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

DanielleRating, 5 stars1 month ago
FANTASTIC! We have stayed in hotels on Key Largo, but staying at Stu’s was a game changer. After our dives, it was easy to rinse off our gear then have more than enough space to relax and not feel cooped up. The entire place was extremely clean. The pool was perfect and the edge of the water was a perfect place to hang out we saw several manatees and even had a pelican visit. Stu was very responsive and we are looking forward to repeating this adventure again!
Guest favourite
Home in Key Largo
4.95 out of 5 average rating, 44 reviews

Cottage in Paradise

WillRating, 5 stars1 week ago
The perfect place to stay while we were visiting our family in the Keys.

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