Beach house holiday rentals in Islamorada

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Popular amenities for Islamorada beach house rentals

Beachfront house rentals

Superhost
Home in Key Largo
4.84 out of 5 average rating, 439 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

AbigailRating, 5 stars2 weeks ago
Great place with good amenities. Views from the roof were amazing. Would absolutely stay here again
Top guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 118 reviews

Paradise found!Key Colony Beach,Cabana Club.

ZoeRating, 5 stars1 week ago
Kari’s place is a slice of paradise! The setting, overlooking the water, is so beautiful. We sat on the balcony watching the birds, enjoying the view. The beds were extremely comfortable, it was so quiet, we all slept like logs each night. The Cabana Club membership was very much appreciated, our kids loved the pool/smoothies/ice cream and we always got a space either on the beach or by the pool. We use the kayaks which was fun. It’s a great base for exploring the keys, we did a daytrip to Key West and went on a snorkeling trip out to Sombrero Reef. Would definitely recommend Kari’s place.
Superhost
Home in Islamorada
5 out of 5 average rating, 3 reviews

Islamorada Cay Home. Elegant home

MarlaRating, 5 stars1 month ago
The outdoor space is absolutely fabulous. The heated pool was enjoyed every day. The property is on the corner of two canals that had pretty clean water. We met several manatees who graced us with their presence often. Fishing was not great during the month so our fishermen were rather disappointed. The interior was very pleasant and cooking was easy. The entire third floor is the master sitting room, bathroom and bedroom. The only drawback for me personally is that the master bathroom is an "open concept " design which left me without a sense of privacy. Isa was extremely helpful and responded quickly with our questions. Thank you Isa!
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 62 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

TinaRating, 5 stars1 month ago
We had a wonderful week. House was beautiful and pool was so relaxing. Loved the location. Ever was friendly and responsive for all questions we had. We would love to go back. 😊
Top guest favourite
Home in Cudjoe Key
5 out of 5 average rating, 20 reviews

Tiki Time in Cudjoe Key 136

LorrieRating, 5 stars1 week ago
This place is beautiful! Amazing views from upper and lower deck, comfortable and very clean home, fun neighborhood with lots to do, great local restaurants. This was truly a relaxing vacation and we are so glad we chose this property. The sunrise is beautiful from this location. We really enjoyed riding the bikes and fishing from the dock. We will be back!
Guest favourite
Home in Marathon
4.8 out of 5 average rating, 60 reviews

7 Mile Ocean Bliss

JenniferRating, 5 stars4 months ago
We had an amazing stay at this beautiful Airbnb in the Keys! The home was stunning, with all the amenities you could ask for, including a relaxing hot tub. The fishing right on the property made it even better – perfect for enjoying the local marine life. The host was incredibly accommodating and made sure we had everything we needed for a perfect getaway. Highly recommend this spot for anyone looking for a peaceful and fun escape!
Guest favourite
Home in Marathon
4.9 out of 5 average rating, 29 reviews

Viamarhe House-Private beach, Kayak, yard games

VeronicaRating, 5 stars1 month ago
We had a wonderful stay! House and property were as pictured and in a great location. We enjoyed lounging on the beach, the kayaks & the ping pong table. At night, the stargazing was amazing; our host, Marjorie, even reminded us to watch for the planetary alignment! We then lit the tiki torches and had a fire in the fire pit - perfect evening! Marjorie was quick to respond when we had a question. The only suggestion we would have is to update a couple of the outside toys. It appears that someone may have been working on the pool table. Our neighbors renting the smaller unit were lovely. Still lots of privacy if that is what one is seeking. Thanks for a great vaca!
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 18 reviews

Marathon Key Colony Beach with Cabana Club passes

NickRating, 5 stars4 months ago
Such a fantastic place to stay - my best ever experience with Airbnb. The garden by the canal is a fantastic place to relax in the evening. The neighbours on both sides were lovely people and so welcoming. Had such a relaxing break. The house is really well equipped - big fridge/freezer, washer/dryer, dishwasher, cooking equipment etc. There’s a Weber BBQ in the garden with all the cooking utensils you’ll need. It’s a really nice, quiet street with some great places to eat and drink nearby and within walking distance. Thoroughly recommend the place. Cheers Nick

Beach house rentals with a pool

Guest favourite
Home in Key Largo
4.79 out of 5 average rating, 24 reviews

Brand new beautiful and modern waterfront home

Mike & KristineRating, 5 stars1 week ago
Great accommodations, quiet location. Definitely look to stay there next time we are there.
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
4.79 out of 5 average rating, 33 reviews

Luxury Waterfront Retreat with Dockage & Pool

MindyRating, 5 stars3 weeks 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
4.9 out of 5 average rating, 10 reviews

Paradise Cove!30ft Dock Pool BBQ

PatrickRating, 5 stars2 days ago
We are a family of 5 that just finished an excellent stay at this waterfront townhome. The house was well decorated, clean and had everything we needed. It also felt bigger inside than we expected. The dock and pool were recently renovated and in perfect condition. There are a few boat ramps nearby - we chose the Boathouse Marina as they also stored our trailer. The kitchen and grill also felt new and made for easy dinners when we chose to stay in. We would absolutely stay here again.
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!!!!
Superhost
Home in Summerland Key
4.88 out of 5 average rating, 32 reviews

Pelico Palms Sunset Suites

AndyRating, 5 stars2 days ago
I had an excellent stay at this apartment last weekend. The place is just like the photos: very beautiful, comfortable, and with a warm atmosphere that makes you feel at home right away. Everything was spotlessly clean and well maintained. The location is perfect for relaxing and disconnecting, and the peaceful surroundings made my experience even better. The hosts were super attentive and friendly, always available for anything I needed. I would definitely recommend this place to other guests, and I’d love to come back. Thank you for such a lovely stay!
Guest favourite
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Golf Coast Oasis

RickRating, 5 stars1 week ago
Madelyn's place was a wonderful place for our family vacation. The heated pool and mini golf were a hit with the grand kids! A great deal of thought has went into the property's landscape to insure privacy. We felt completely at home. Plenty of spaces for everyone to go off and have "alone time". Most everything there is self explanatory, however Madelyn was proactive in contact with us should we have had any questions. We are definitely considering this place in future visit to the Keys!
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 110 reviews

Anglers Terrace, CondĂŠ Nast Traveler's Best Airbnb

JaynaRating, 5 stars2 weeks ago
We enjoyed our stay and look forward to returning! Home was in a convenient location to many restaurants and grocery stores. Andy’s response was quick when asking about nearby suggestions for items to rent and suggestions about specific excursions. Beds were comfortable and home was clean. He dropped bagels off one morning and even ordered an additional Alexa and delivered that when it arrived. We were happy with our decision and look forward to visiting again. Thanks Andy!

Private beach house rentals

Guest favourite
Home in Marathon
4.91 out of 5 average rating, 46 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

RebeccaRating, 5 stars3 days 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!!
Superhost
Home in Key Colony Beach
4.94 out of 5 average rating, 17 reviews

Pelagic Paradise. On Canal, Dock, Pool Club Free!

KathrineRating, 5 stars1 month ago
We really enjoyed our stay at Keys 2 Joy. It's located right in Key Colony Beach with access to anything you need within a quick drive. The house was very clean, decorated nicely, owners communicated clear directions and entrance instructions, and everything we needed was provided. They even had some toys stowed away and my 2 small kids loved it. The layout of the house is different than expected with 2 entrances that come into bedrooms, but it wasn't an issue since we put the kids in the middle room. Kitchen had anything we needed, fridge had an ice maker, there's room for a boat, and even a few poles to fish off the dock. We had our dog with us also and they neighborhood is super walkable and friendly. Would stay here again for sure, thanks!
Superhost
Home in Cudjoe Key
4.88 out of 5 average rating, 34 reviews

Lower Keys Paradise

AhrinRating, 5 stars6 days ago
Great place to stay. It’s a house in a community with a lot of activities available. There’s an extra $125 fee for that, but it’s worth it.
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 57 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

StephenRating, 5 stars1 month ago
Wonderful home. Everything was very clean and very well stocked.
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 17 reviews

Keys to the Sea + Cabana Club

OliviaRating, 5 stars4 days ago
5 stars are not enough ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ We loved our stay- it was perfect. The house, the view, we had everything we needed and more. Michael was super polite and answered on every question in a couple of minutes. Location is also great! We would love to come back! Thank you so much
Superhost
Home in Tavernier
4.85 out of 5 average rating, 20 reviews

Waterfront Home Near Key Largo | Long-Term Stay

ShawndaRating, 5 stars1 week ago
Quiet location, close to lots of activities and loved the canal access!
Guest favourite
Home in Key Largo
4.88 out of 5 average rating, 121 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

DanielleRating, 5 stars1 week 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!
Superhost
Home in Key Largo
4.83 out of 5 average rating, 12 reviews

The Ultimate Bay View Home

NicoleRating, 5 stars4 months ago
I recently stayed at Adriana’s beautiful waterfront Airbnb in Key Largo while in town for a wedding, and it was everything I could’ve hoped for. The views are absolutely breathtaking – you’re right on the water, so you get to wake up and unwind with the most serene backdrop. The house itself was pristine, showing how much care and attention Adriana puts into every detail. Adriana was an amazing host, incredibly responsive and genuinely helpful from the start of our stay to the finish. She made sure everything was in perfect order and was always just a message away if we needed anything. A huge plus was being able to bring my two dogs along, which made the experience even more memorable. They loved exploring the area as much as I did! Overall, it was a fantastic experience, and I would absolutely stay here again. If you’re looking for a relaxing waterfront getaway in Key Largo, Adriana’s place is a gem!

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