Beach house vacation rentals in Islamorada

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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 stars1 month 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.
Superhost
Home in Key Largo
4.84 out of 5 average rating, 438 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

MatthewRating, 5 stars1 month ago
We had a great time in Key Largo! Home is on a quiet street with excellent water views! We would certainly return in the future!
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 favorite
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 favorite
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 favorite
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!
Superhost
Home in Key Largo
4.78 out of 5 average rating, 46 reviews

Oceanfront Seaside Escape

JenniferRating, 5 stars4 weeks ago
Perfect spot for a bachelorette trip! The private beach and dock area was amazing! Also close to restaurants
Guest favorite
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!

Beach house rentals with a pool

Guest favorite
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.
Superhost
Home in Marathon
5 out of 5 average rating, 18 reviews

W09 - New Luxury Property! Breathtaking Canal Fron

KImRating, 5 stars1 month ago
This was our 2nd stay at the house it a big and nice for our group! Just needs a little update and some extra kitchen towels which we did get just little stuff. But for the most part we had a wonderful trip 😊
Guest favorite
Home in Marathon
4.93 out of 5 average rating, 15 reviews

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

RicheleRating, 5 stars2 weeks ago
Great home for a family vacation. Enjoyed the pool and all that Marathon has to offer. Plenty of room for everyone to spread out. Great decks and the tiki hut was a perfect place to hang out when you wanted to be outside but not in the sun. Bert was incredibly helpful and responsive.
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 favorite
Home in Key Colony Beach
4.9 out of 5 average rating, 10 reviews

Paradise Cove!30ft Dock Pool BBQ

PatrickRating, 5 stars1 day 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 Summerland Key
5 out of 5 average rating, 10 reviews

Pelico Palm Villa

KellyRating, 5 stars12 months ago
This home was absolutely beautiful!! It was exactly what we had hoped for, We were a family of 4 with my husband and I, with are two sons, ages 17 & 20, plus ones girlfriend age 16. We wanted a nice family vacation without the spring break chaos & this was it! This home was so clean yet cozy, had all the necessities we needed, everyone had their own room and bathroom which was super!!! This home could definitely accomodate so many more if you wanted to do so. We were the only ones there at the time, so we had the pool area to ourselves which we loved sooooo much! We played bags by the pool daily, swam during day & at night. The home had a great deck with a wonderful grill, we made slushy drinks with the ninja blender, anything you wanted this place had! We traveled to Key West a couple times which was nice and close, about a 30 minute drive. All in all this place is top notch! Don't hesitate to book! It's worth it!! LOVED this Home!! & Nate was a spectacular host!!!
Guest favorite
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 favorite
Home in Marathon
4.96 out of 5 average rating, 110 reviews

Anglers Terrace, Condé 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

Top guest favorite
Home in Key Largo
4.94 out of 5 average rating, 79 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

BrittanyRating, 5 stars1 week ago
We had everything we needed! Stu was helpful and responsive. We had a fantastic time and will be back in the future! Don’t miss a chance to stay here in Key Largo. Great location and loved keeping the boat behind the house. House is very clean and has all of the amenities you could possibly think of!! 10/10 recommend!
Guest favorite
Home in Marathon
4.91 out of 5 average rating, 46 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

RebeccaRating, 5 stars2 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 Upper Sugarloaf Key
4.7 out of 5 average rating, 84 reviews

Palm - Bungalows Sugarloaf Beach Key West

DanaRating, 5 stars4 weeks ago
What a relaxing and fun stay! I loved that we could use kuyack and paddle boards. Our place was just right. Beds were comfortable. Very clean. No complaints. Loved the pool, too. Can't wait to plan our next trip there. Our host was very attentive.
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 stars5 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 favorite
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 favorite
Home in Key Colony Beach
5 out of 5 average rating, 16 reviews

Keys to the Sea + Cabana Club

ConnorRating, 5 stars2 weeks ago
I did not speak with Michael much throughout our visit. That is because we ran into zero issues, everything we needed was available to us.
Superhost
Home in Tavernier
4.85 out of 5 average rating, 20 reviews

Waterfront Home Near Key Largo | Long-Term Stay

ChristopherRating, 5 stars2 months ago
My group and I had an amazing stay! Corey and Armando were amazing hosts; super responsive to any questions and flexible to my requests. They even provided great recommendations for things to do in the area. Home was beautiful and in a great area. I would definitely stay here again!

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