Beachfront vacation rentals in Islamorada

Find and book unique beachfront homes on Airbnb

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Popular amenities for Islamorada beachfront rentals

Beachfront home rentals with a pool

Superhost
A light blue house is prominently featured, elevated above ground level with a staircase leading to the entrance. Palm trees surround the property, creating a tropical ambiance. Nearby homes display a mixture of colors, enhancing the neighborhood's coastal charm.
Home in Marathon
4.89 out of 5 average rating, 19 reviews

Sombrero Beach Getaway

JoshuaRating, 5 stars3 weeks ago
Sombrero Beach Getaway was perfect for our family of 4! The location, pool, well-equipped kitchen, and elevated deck all contributed to a great stay in Marathon.
Superhost
A private outdoor space is featured, showcasing a clear blue pool surrounded by lounge chairs and a dining area with chic striped umbrellas. Lush palm trees provide shade, while a stone pathway leads to the waterfront, enhancing the coastal ambiance.
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
A serene outdoor space features a heated pool adjacent to a relaxing spa, framed by swaying palm trees. Sun loungers sit beside the water, while the distant dock and lush landscaping create a tranquil ambiance.
Home in Marathon
4.93 out of 5 average rating, 15 reviews

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

RicheleRating, 5 stars1 month 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
A scenic pool area is visible, featuring a hot tub adjacent to the water's edge. Palm trees sway gently in the breeze, providing a tropical atmosphere. The blue sky reflects on the tranquil water, enhancing the serene setting.
Home in Marathon
4.73 out of 5 average rating, 22 reviews

Sunset Views, Pool and Dock

AllenRating, 5 stars2 months ago
We really liked the location. It was peaceful and private and a great neighborhood to walk around and to walk our dog. Yet, a short drive into Marathon for restaurants or any other needs. The house isn’t new but it was exactly as represented and it was perfect for us. Frank was very responsive. There were a couple of issues that he addressed immediately. It wasn’t his fault that because of the location, receiving repair parts can take some time. But Frank took care of our situations.
Guest favorite
Home in Key Colony Beach
4.91 out of 5 average rating, 11 reviews

Paradise Cove!30ft Dock Pool BBQ

PatrickRating, 5 stars2 weeks 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 Key Colony Beach
4.73 out of 5 average rating, 134 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

CherylRating, 5 stars3 months ago
Mary's place was in a very safe and beautiful location. Everyone was friendly and there were endless dining options. There were even local conveniences that I didn't expect nearby such as Dollar Tree, Winn Dixie, Home Depot, etc. Showers had great water pressure, hot water, and had zero sulphur smell. Decor was lovely and ample storage space for your things. A/C and heat works great and no musty smells anywhere. Beds, outdoor furniture and couches very comfortable. Convenient off-street parking. Was too busy to enjoy the cabana amenities but visited it briefly and it looked wonderful. Thank you Mary hope to return in the future!
Superhost
A private pool area features a sparkling blue pool alongside a smaller splash pool. Lounge chairs are arranged around the pool deck, with a shaded pergola providing space for outdoor dining and seating. Lush greenery enhances the tropical ambiance.
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars2 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.
Superhost
A peaceful waterfront view features a sandy area leading to calm waters. A thatched-roof structure provides shade, while lounge chairs are arranged for relaxation. Boat ramps and a dock are visible, offering accessibility to the water for various activities.
Home in Key Largo
4.83 out of 5 average rating, 12 reviews

The Ultimate Bay View Home

NicoleRating, 5 stars5 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!

Beachfront home rentals with a hot tub

Guest favorite
Home in Key Colony Beach
5 out of 5 average rating, 5 reviews

Huge Swim Spa~ Incredible Special Fall Pricing

MatthewRating, 5 stars1 month ago
We really enjoyed our stay. The host, Sherry, gave timely information and quickly responded to messages. We were pleasantly surprised by the number of amenities that were available to us at the house. The Cabana Club was a real hit with my teenage daughters. It had reasonably priced drinks and lunch type meals. They enjoyed just laying by the pool or beach and sun tanning. We saw manatees one of the evenings right in the backyard of the home.
Guest favorite
Home in Marathon
4.91 out of 5 average rating, 47 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

RebeccaRating, 5 stars2 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!!
Superhost
A clean and modern pool area is visible, featuring a sparkling blue pool with a connected hot tub. Lounge chairs are positioned around the pool, with the surrounding space designed with light-colored tiles. Lush greenery and water access are seen in the background.
Home in Marathon
5 out of 5 average rating, 10 reviews

Oceanside Oasis 2bed/2bath with brand new private

MeredithRating, 5 stars4 weeks ago
The pool and outdoor living space at the house was fantastic. The inside was a little outdated but everything functioned fine and was very comfortable for our family of 6. The dock was great for our boat with easy access to lots of fun things on the water.
Guest favorite
A spacious living room features a light color palette with a large flat-screen television mounted on the wall. Comfortable seating is arranged around a coffee table, and large windows provide a view of the ocean and natural light. Coastal decor enhances the atmosphere.
Condo in Tavernier
4.9 out of 5 average rating, 118 reviews

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

MarkRating, 5 stars2 weeks ago
If you like peace and quiet this is the place. Not much of a shopping destination though. Key largo is more for snorkeling and scuba. A 2 hour drive to key west.
Guest favorite
A light-filled living area features a blue sofa with decorative pillows and a wooden coffee table atop a woven area rug. Two accent chairs frame the seating arrangement, while natural decor elements, including tall grasses and wall art, enhance the welcoming ambiance.
Apartment in Tavernier
4.95 out of 5 average rating, 190 reviews

Boho FL Keys Condo

RylanRating, 5 stars2 weeks ago
My husband and I had a wonderful stay with our two children. The Keys Escape was clean and very comfortable. We loved sitting out on the balcony in the mornings and evenings as the view was incredible. The heated pool was awesome, and just a few steps away. Highly recommend!
Superhost
A pair of outdoor chairs is positioned on a balcony, overlooking a vibrant canal. Palm trees and neighboring homes line the waterway, while a bright sky filled with fluffy clouds enhances the serene waterfront view.
Home in Cudjoe Key
4.87 out of 5 average rating, 101 reviews

Island Oasis ~ YOUR Paradise Awaits!

PamRating, 5 stars2 weeks ago
As soon as we walked in we felt right at home. We were celebrating my 65th bday week.Bonnie even had me a bday cake in the freezer .Power was destined to be out for several hours one day they brought us a small plug and play generator to run coffee pot hair dryer etc. My only disappointment was we could not use the Kayak's due to the sludge in the canal. That was not any fault of Bonnie or Joe's just mother nature. We had the pleasure of meeting the awesome host and hostess very nice people indeed. Loved their home and hospitality. If we ever come back will stay here again. Very comfortable bed. Clean and comfortable very relaxing.Nice resort and amenities very nice pool.
Top guest favorite
A well-lit living area showcases a comfortable sectional sofa and a wooden dining table with light-colored chairs. A decorative bowl of lemons sits at the center of the table, while large windows offer views of the surrounding landscape and allow natural light to fill the space.
Condo in Tavernier
4.94 out of 5 average rating, 123 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

DanelleRating, 5 stars1 week ago
We loved our stay at Nicole’s place. It was well stocked, super clean, and the decore was lovely. This is second time at Ocean Pointe. We enjoyed being in building 5 and the larger corner unit.
Superhost
Townhouse in Key Largo
4.84 out of 5 average rating, 105 reviews

Oceanfront Resort W/Indoor Pickleball - Spacious!

BreannaRating, 5 stars1 month ago
Great place to stay with kids. They loved the pools and game room. Place was clean and spacious! He was a great host, very responsive. Would stay again!

Pet-friendly beachfront home rentals

Guest favorite
Home in Tavernier
4.96 out of 5 average rating, 98 reviews

Sunset Beach Hideaway *Private Beach* *Jacuzzi*

SteveRating, 5 stars3 weeks ago
this is a place we will stay at each year for spring break. my kids didnt want to leave - it has everything. we were very impressed. My wife and i had our own house. the kids stayed in their own house. quiet, beautiful grassy areas and trails. We had morning coffee on the private beach and took paddle boards and kayaks out at sunset. thank you Diane for the amazing houses, beach, location etc. We will be back next year :):)
Guest favorite
The exterior of the beach house is showcased, featuring a bright white facade and a unique geometric design on the railings. A spacious outdoor area is visible, adorned with lounge chairs and a shaded patio table, surrounded by crushed white stone and greenery.
Home in Marathon
5 out of 5 average rating, 17 reviews

Seaside Sunrise. Newly remodeled waterfront

JonathynRating, 5 stars1 month ago
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.
Top guest favorite
Home in Marathon
4.89 out of 5 average rating, 37 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

LydiaRating, 5 stars7 months ago
We booked this home last minute and now have our go-to vacation spot in Marathon! Alida is a friendly host with great communication. The home is very clean. Beds are very comfortable. Kitchen is well stocked with pots, pans, etc. The kayaks and paddle board made our vacation even more special! The steet is very quiet and peaceful. The setting in the back yard is very private, as is the long dock. We had a 23' rental boat for our stay. The view is amazing and the sunsets are a special treat each evening. I very much appreciated the ample, comfortable seating everywhere - inside and outside of the home. Thank you Alida. We made great family memories here!
Guest favorite
A sandy shoreline is bordered by swaying palm trees, providing a peaceful oceanfront view. A yellow kayak rests on the beach, while a hammock is visible nearby, adding to the tranquil setting. The distant jetty extends into the calm sea, enhancing the serene atmosphere.
Guesthouse in Marathon
4.95 out of 5 average rating, 21 reviews

The Pink Dolphin House.

PatrickRating, 5 stars1 week ago
Beautiful ocean views and great local recommendations from the host! Some aspects of the interior were a bit dated, but with multiple areas to enjoy the outdoors (offering full shade to full sun and everything in between), we didn't do much inside except sleep. Kids spent hours per day in the pool and adults most enjoyed lounging on the jetty with 345 degrees of ocean views. Board games (and a ps3) were available for the occasional down time. The location allows for a feeling of privacy on the ocean while offering many hidden gems for dining and activities nearby.
Superhost
Bungalow in Key Colony Beach
4.67 out of 5 average rating, 6 reviews

Coral Quay-III Canal waterfront,access BEACH club!

JamesRating, 5 stars48 months ago
We had an amazing time at this property. The location was couldn't get any better. We brought our boat and property was perfect for that. We are already starting to plan for next year!
Guest favorite
The exterior of the vacation home is framed by vibrant palm trees, providing a tropical feel. A white staircase leads to the covered front porch, which features a round glass door. Decorative stone landscaping complements the structure, enhancing its inviting appearance.
Home in Cudjoe Key
4.93 out of 5 average rating, 45 reviews

Private Ocean Oasis by Key West, Florida

DonnaRating, 5 stars3 months ago
This was the perfect place to meet up for a Christmas gathering with our adult children. The home was so nicely decorated and furnished and had EVERYTHING we could have needed for a three day stay. There was plenty to do on the Venture Out Resort property and anything else you’d want or need is within driving distance. Will definitely stay here again!
Guest favorite
A spacious bedroom is highlighted by a comfortable wooden bed with patterned linens. A bedside lamp casts a warm glow. Floor-to-ceiling windows offer views of the beach, with outdoor seating visible on the patio. Tropical decor adds a subtle touch of elegance.
Home in Marathon
4.92 out of 5 average rating, 25 reviews

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club

StephanieRating, 5 stars3 weeks ago
The host Brian was attentive and responsive. The house was comfortable and well-furnished. The location on the water was beautiful, yet also private. A great home base for our family to enjoy exploring all that the Keys have to offer!
Superhost
A two-story home is set along a deep canal, featuring wooden decks that overlook the water. Lush palm trees and shrubbery frame the property, while a swimming pool and a boat can be seen nearby, enhancing the serene waterfront setting.
Home in Islamorada
4.86 out of 5 average rating, 7 reviews

Venetian Tropics private heated pool at 82 degrees

JessicaRating, 5 stars7 months ago
I’d like to start this review with JoAn is amazing and super responsive. If you need anything, she will ensure that you will get it. This house is the epitome of what you would expect for a Florida keys home. If you’re looking for a house with a lot of character, in a phenomenal location for Atlantic access and fuel, this is the place. We throughly enjoyed our time staying here and will be back next year. The pool was nice to get into after diving every day, there was a fresh water hose on the dock, a freshwater outside shower and even a fish cleaning station. There is a deep freezer for ice and a tiki bar outside with a sink. Couldn’t be any happier with the house or the host. Thanks again JoAn for letting us use your house.

Quick stats about beachfront rentals in Islamorada

  • Total rentals

    280 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    1K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    170 properties allow pets

  • Rentals with a pool

    220 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Beachfront rentals