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, 436 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

AtRating, 5 stars2 weeks ago
This house was just as described and in a great location in a quiet neighborhood. It was perfect for our family!
Guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 115 reviews

Super savings, Key Colony Beach,Cabana Club.

DerekRating, 5 stars2 weeks ago
The house is in great condition and the furniture and decor is very nice. Kari has thought of everything for the property you may need during your stay both inside and out. Having access to the canal to dock your boat is very convenient and we made use of the paddleboard kayaks. Love the Cabana Club and Sunset Park for things to do close by. Location wise it's wonderful, walkable to everything in Key Colony Beach. We would definitely stay here again, wonderful place, location and great owners.
Superhost
Home in Marathon
4.95 out of 5 average rating, 20 reviews

4BR Sombrero Beach House on Canal w Dock & Pool

JosephRating, 5 stars3 weeks ago
Matt was super responsive and helpful with any issues we had. The house was comfortable and the proximity to the beach was amazing (5 minute walk). We stayed for a month with a 1 year old and a big dog and found the house perfect for our needs. Manatees even came up to the house on our last day! Super special. Would recommend.
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 62 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

TinaRating, 5 stars3 weeks 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. 😊
Guest favourite
Home in Marathon
4.81 out of 5 average rating, 59 reviews

7 Mile Ocean Bliss

JenniferRating, 5 stars3 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
4.93 out of 5 average rating, 41 reviews

Tropical Dream Vacation - 3bdrm/2bath CANAL FRONT!

ThomasRating, 5 stars2 weeks ago
My wife and I stayed at Ernesto’s place with another couple in early February, escaping the Illinois winter. We loved our stay! The house was beautiful and fully fitted with everything that we would need. Ernesto was always very quick to respond to any questions we had, and he was very friendly and helpful. Beds were comfortable and showers were great. Our favorite part was the pool — bigger than it looked in the photos! We spent most afternoons there and some evenings, too. We spent the extra bit to have it heated, and that was well worth the money. The house is an easy walk or bike ride to beautiful Sombrero Beach. It is also very close to a Publix grocery store and many wonderful restaurants. Just over an hour’s drive got us to Key West for a fun day there. We would stay here again in a heartbeat! Highly recommend!!
Superhost
Home in Key Largo
4.77 out of 5 average rating, 43 reviews

Oceanfront Seaside Escape

RalphRating, 5 stars3 weeks ago
My stay at this Airbnb was fantastic! The place was clean, comfortable, and well-equipped, making it a perfect home away from home. The check-in process was smooth, and the host was very responsive and accommodating. I highly recommend this spot to anyone looking for a cozy, convenient place to stay!
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 26 reviews

Viamarhe House-Private beach, Kayak, yard games

BrianRating, 5 stars3 days ago
Frequent visitor to the Keys and Marathon, value of price for what you get is top notch. Beautiful home that holds more people than it looks like, especially with the outdoor spaces and double bunk beds. One of the best stocked homes we’ve stayed at and definitely clean!! Traveled with teenagers and they never complained - perfect amount of activities at home keep them busy when we were chillin. Seriously could write a novel on all the details. The information given from Marjorie is spot on and she is super responsive making sure everything is going smoothly. Beach is as described, if you’ve visited the Keys you understand. That does not detract from the beauty of having your own private beach!! You just won’t go swimming there. Having a private fire on the beach more than makes up for that. Plenty of great swimming beaches elsewhere in the Keys. There is a small cabin rental in back, would be nice to have the option to book both on the same page. We will be back! đŸïž

Beach house rentals with a pool

Guest favourite
Home in Key Largo
4.76 out of 5 average rating, 21 reviews

Brand new beautiful and modern waterfront home

BrittanyRating, 5 stars6 days ago
The rental is located in a gated campsite that includes both houses and campers. The campground is quiet and has views of the ocean to watch the sunset. The rental has a lovely ground level with a large tv, grill, dining area, and outdoor furniture. The inside of the rental was extremely clean upon our arrival. Both beds were nice and comfy. The kitchen and bathrooms had all necessary items. We appreciate Claudia sharing her place in Key Largo for us and our pups.
Superhost
Home in Marathon
5 out of 5 average rating, 17 reviews

W09 - New Luxury Property! Breathtaking Canal Fron

TaraRating, 5 stars1 month ago
This place was exactly what our families were looking for. We traveled with 2 families, ages 16-50+. Private, spacious, good fishing right in the back yard. We were interested in private, quiet, family time and that’s exactly what we got. Every bedroom had own bathroom which was a bonus. Home was very spacious and allowed everyone to spread out. There is a small beach within walking distance that is marginal with a better beach about 15 min away. We found a few good restaurants nearby and a did a lovely pontoon charter for the day, stopping at local restaurants along the way. Key west is about an hour drive if you are looking for some excitement with other lovely towns along the way. The host was responsive and easy to work with. Plus a great price. We would definitely stay again.
Superhost
Home in Marathon
4.93 out of 5 average rating, 14 reviews

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

JoshuaRating, 5 stars3 months ago
We were looking for a great place close to a small beach, an ocean view, which was clean and could house our family comfortably. This place did that and provided a place away from tourist crowds. Very nice place
Superhost
Home in Marathon
4.78 out of 5 average rating, 32 reviews

Luxury Waterfront Retreat with Dockage & Pool

DonRating, 5 stars1 month ago
Last minute booking with Naomi due to problem with another Airbnb on Cudjoe Key. Naomi immediately responded and made arrangements to get us settled. Her place was easy to find, with a lot of amenities provided. Kayaks, hot tub, pool and fishing were easy to access and enjoy.
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 7 reviews

Paradise Cove!30ft Dock Pool BBQ

WymanRating, 5 stars3 days ago
My family and I had a great time here! It was the perfect house, super clean and just as described! Yuni was always quick to respond and answer any questions. We had no intentions of renting a boat, but just up the road was an easy rental spot and we were able to tie the boat up right outside the door. Everything we needed was within a few minutes and the location was perfect to take a drive down to Key West! We will absolutely plan to return!
Superhost
Home in Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars2 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
4.88 out of 5 average rating, 17 reviews

Golf Coast Oasis

JudithRating, 5 stars2 weeks ago
We had a lovely month at Madelyn’s home. Outdoor areas including heated pool were extraordinary. Our host and property manager were responsive and helpful. We look forward to returning.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 107 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

PattiRating, 5 stars2 weeks ago
Andy’s place was absolutely stunning and very comfortable. He was very responsive to our requests and questions and made our stay exceptional. We especially enjoyed relaxing in the pool and sitting on the deck where we watched the boats glide by. The kitchen was well stocked and had plenty of space for us to store our groceries and other sundries. The bedrooms were quite comfortable and the bathrooms were modern and clean. We hope to return again next year.

Private beach house rentals

Guest favourite
Home in Key Largo
4.97 out of 5 average rating, 91 reviews

The Paradise 2

KaliRating, 5 stars5 days ago
What a beautiful spot! We loved the view off the deck and Luis' place was clean, well stocked with everything we needed and perfectly situated for my family of 4. My kids (10 and 7) loved the little bunk area. It was a bit off the beaten path to get to other 'things to do' in Key Largo, but that may be a perk for some! Overall, we were very happy with our stay.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 43 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

MaryRating, 5 stars2 weeks ago
If you’re looking for a place in the keys Casa Kokomo will not disappoint. This place has it all, is so well equipped, and the location could not be better. We could walk to Publix and Walgreens. The Cracked Conch Cafe is a great little breakfast spot and a must get is the fried cracked conch. My husband worked for Ritz Carlton much of his career in the hospitality industry and Kokomo gives you the same level of luxury you’d expect from the highest level quality hotel brands; from the linens on the beds to the cozy robes. We like to fish and rented a boat that we parked out back on the private dock. The back yard is so private and is an oasis. If you’re like us and you work hard to enjoy your vacation time, choose Casa Kokomo, you won’t be disappointed.
Superhost
Home in Key Colony Beach
4.94 out of 5 average rating, 16 reviews

Pelagic. Canal. Pool Club. Feb Open! Cancellation

LisaRating, 5 stars1 month ago
We loved this Airbnb home. It was half of a one level duplex right on an island. Having access to the Cabana Pool House was key. We walked to the pool house that had a pool, hot tub, bar, and access to a great beach. Restaurants were walkable. Great sunsets at sunset park on the island. We loved everything about the island and home! My family loved golfing at the park 3 course many times too. The only missing items were cleaning products, dish soap and garbage bags. Sitting in the cozy couch outside by the dock was a perfect way to end the day. Having access to fishing poles was perfect for our family. Thank you for a wonderful family stay! Definitely recommend this Airbnb if you are coming to the keys!
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 57 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

StephenRating, 5 stars3 weeks ago
Wonderful home. Everything was very clean and very well stocked.
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 12 reviews

Keys to the Sea + Cabana Club

AlynRating, 5 stars5 days ago
Our stay at Michael’s home was absolutely wonderful. The house was perfect, the sunrises and sunsets were gorgeous!!! The dang water pressure was AWESOME in the shower!!! Michael gave us suggestions for restaurants and local things to do. We were close to shopping, dining, could walk to the pool & local weekly farmers market!! Michael was always quick to respond!! We had a boat and the local marina is just a couple of doors down and they let us keep the trailer there for a weekly rate of $125! Havana Jacks is right around the corner for live music at night and we enjoyed Sparkys! This was our first time to the area! Just minutes from the airport where we rented a convertible for the day to Key West!!!! Well worth it!!! Thank you for an awesome stay! We are already planning our trip back!!
Superhost
Home in Tavernier
4.89 out of 5 average rating, 18 reviews

Waterfront Home Near Key Largo | Long-Term Stay

ChristopherRating, 5 stars1 month 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!
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 18 reviews

Casa Blanca

TamiRating, 5 stars3 days ago
We love this home and this was our second time staying here. We love being able to have our own Washer/dryer and the home comes with many towels (for showering and the beach/pool) and linens/blankets. The location, size and price are perfect.
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 66 reviews

Private 174ft Dock, Boat Launch, Sombrero Beach

AmandaRating, 5 stars7 months ago
Beautiful location and house, we really enjoyed our stay! We had a few questions for the host and they were immediately responsive. Would stay here again for my next visit to Marathon!

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