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
4.9 out of 5 average rating, 20 reviews

Sombrero Beach Getaway

SteveRating, 5 stars3 weeks ago
We enjoyed our stay very much. He was always very responsive and took care of anything we needed. Might be coming back another time in the future.
Superhost
A private balcony is furnished with a glass-top table and woven chairs, offering a serene view of palm trees and a sandy beach area. The calm water reflects a clear sky, creating a peaceful atmosphere for relaxation.
Home in Marathon
4.69 out of 5 average rating, 16 reviews

#7 Waterfront 4Bed 3Bath Pool Home

CarolRating, 5 stars11 months ago
Location, location, location! Great views, nice pool area, dock space if needed. Walkable to several resorts and turtle sanctuary.
Guest favorite
A waterfront patio features comfortable wicker seating overlooking serene water. The setting sun casts a warm glow, illuminating the scene with subtle light. Colorful decorations hang from the thatched roof, complementing the tranquil atmosphere while boats are visible in the distance.
Home in Key Largo
4.97 out of 5 average rating, 101 reviews

The Paradise 2

LeanneRating, 5 stars3 days ago
We really enjoyed our stay. It completely matched the description, the patio was amazing, and the place was well stocked with everything we needed. It had many personal touches which made us feel at home. It was a great fit for two adults and 2 kids. Our time on the porch in the morning and relaxing in the evenings were the best part. Highly recommend!
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
4.75 out of 5 average rating, 24 reviews

Sunset Views, Pool and Dock

JamesRating, 5 stars1 week ago
We stayed at Frank’s place for two weeks and had an absolutely amazing time! The house was spotless, well-equipped, and super practical for our two energetic little ones. The pool and hot tub were perfect. We made the most of every sunset soaking in the hot tub, followed by peaceful late-night floats in the pool under clear, starry skies. We fished off the jetty most days and caught barracuda, mangrove snapper, plenty of sharks—and the neighbors even hooked a tarpon and landed a grouper! The kids loved snorkeling right off the dock, spotting rays, turtles, and loads of colorful fish. We missed the manatees when they came by one morning, but luckily caught up with them later while kayaking through the mangroves. Huge thanks to Frank for being such a fantastic host. One day we had a small issue with the pool, and his team showed up in under 10—absolutely amazing service. We truly didn’t want to leave and would come back in a heartbeat. Highly recommended!
Guest favorite
Home in Key Colony Beach
4.92 out of 5 average rating, 12 reviews

Paradise Cove!30ft Dock Pool BBQ

MelissaRating, 5 stars2 weeks 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 Key Colony Beach
4.74 out of 5 average rating, 137 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

LynnRating, 5 stars4 days ago
This home was great! There was six of us staying in this rental. It was spacious for all of us. We loved sitting outside on the patio by the canal. We were able to walk to a local restaurant, beach and pool. The house was very clean and the neighborhood was super quiet. Overall a great stay and Mary was an excellent host!
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 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.
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 stars4 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, 11 reviews

Oceanside Oasis 2bed/2bath with brand new private

AshleyRating, 5 stars2 weeks ago
We came on vacation with our three kids (ages 4, 2, and 2 months), and this place was absolutely perfect for our family. The two-bedroom setup worked so well for us, and the pool was a huge hit with the kids. We especially loved relaxing on the front porch — it overlooks everything and made us feel like we didn’t need to go anywhere else. Being right on the canal was a bonus, especially for fishing. The only thing we wish the home had was a few basic cleaning supplies, but overall, it was a wonderful stay and one we’d definitely recommend!
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, 120 reviews

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

JeffRating, 5 stars1 week ago
This place checked all the boxes! The location of this particular unit was awesome. Close to the pool, but not too close. A short walk to the beach area, and those views from the balcony are second to none. Largo is very responsive and very easy to communicate with. Tavernier Key is the perfect location to many activities. Our family misses this trip already.
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, 193 reviews

Boho FL Keys Condo

KevinRating, 5 stars1 week ago
The location, condo, grounds, access to restaurants and proximity to our fishing destination made this stay enjoyable. At the top of our list for our next trip.
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, 104 reviews

Island Oasis ~ YOUR Paradise Awaits!

AbbyRating, 5 stars2 weeks ago
Bonnie was a nice, responsive host and even brought us additional kayaks to use. We had a great stay!
Superhost
The exterior of a mid-rise home is shown, featuring a light-colored facade and a set of stairs leading to an elevated porch. The porch area is equipped with a table and umbrella, surrounded by tropical landscaping and a gravel driveway.
Cottage in Cudjoe Key
4.64 out of 5 average rating, 111 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

Elizabeth CarmenRating, 5 stars1 month ago
Jason’s place was a great place to stay in the keys!! Jason is great at responding great location, clean house only the couch could use a cleaning. It would have been nice if there were trash bags, extra hand soap and extra toilet paper. Other then that it was perfect!!
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 stars3 weeks 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.

Pet-friendly beachfront home rentals

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 stars8 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!
Superhost
A bright sleeping area features a spacious bed with a light-colored comforter. Two lamps provide soft lighting beside the bed. A desk with a wicker chair is positioned near a window, and an arched balcony door leads to a view outside, framed by light curtains.
Condo in Marathon
5 out of 5 average rating, 3 reviews

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants

MichaelneuroRating, 5 stars3 months ago
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.
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 stars3 weeks 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, 46 reviews

Private Ocean Oasis by Key West, Florida

JeremyRating, 5 stars4 days ago
Awesome place , well described in a perfect location . The amenities in the resort were awesome, lots to do. Ronda was very responsive with my questions I had about the area and things to do thru out. Will definitely be rebooking with her in the near future. Thanks again Ronda!
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
4.89 out of 5 average rating, 28 reviews

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

SarahRating, 5 stars1 day ago
Our family of 8 stayed for a week and found the accommodations absolutely perfect. The beds were comfortable and clean. I loved the ceiling fans and feeling the ocean breeze through the sliding screen door at night. Plenty of closet space to unpack and the outdoor living area was a dream. We played shuffleboard and grilled out a lot. Excellent lounge chairs made stargazing a delight. Great shower pressure and plenty of towels provided. Washer and dryer worked well, as did all of the kitchen appliances. Only 3 out of the 4 bikes were useable; one of them needs a tune up; handlebars were loose and made riding unsafe. Be warned there are no bike helmets. We didn’t use the paddle boards or kayaks because it was a very windy week and the current was strong but they looked to be in good repair and there were multiple life jackets and water shoes and pool noodles available. Loved the pool and beach access at the clubhouse!
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

    ﺩ.ﺇ294 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