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Beachfront vacation rentals in Fiesta Key

Find and book unique beachfront homes on Airbnb

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Popular amenities for Fiesta Key beachfront rentals

Pet-friendly beachfront home rentals

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 stars9 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
Guesthouse in Marathon
4.95 out of 5 average rating, 21 reviews

The Pink Dolphin House.

PatrickRating, 5 stars2 months 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
A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.
Houseboat in Key West
4.87 out of 5 average rating, 246 reviews

Key West Luxury Houseboat at Yacht Club Resort

GarrettRating, 5 stars1 month ago
We stayed in two smaller house boats while we were there before brads. Rectangular shaped single stories with a flat roof area for lounging. They were beautiful.. but unstable, uncomfortable, limited in space, no hot water, had to shower 200 yards away, awful mosquitos, no reliable internet, lack of kitchen ability, I’m 32 my wife is 30 and our son was five months. Pretty looking, but miserable. Especially if wind wasn’t below 5mph. Not to mention the toilets had problems on both! When we got to brads house boat Holly Cow! What a difference. What a relief. Multiple rooms, comfortable beds, no issues with hot water or internet or kitchen. The space was excessive. Very comfortable. Needed some TLC inside but overall it was fantastic. Everything worked like a real 2br 3ba home. I will book this boat everytime as long as it lives. Private marina, quiet, great neighboring boats. Private outdoor waterfront recreational areas. 100% best key west experience I’ve had and I go every year.
Guest favorite
The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.
Home in Marathon
4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars4 weeks ago
We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!
Guest favorite
The spacious canal-front home is showcased from an aerial view, highlighting its private pool and lush palm trees. A dock with boat access extends into the water, while comfortable outdoor seating is positioned nearby, creating a relaxed atmosphere for guests.
Home in Marathon
5 out of 5 average rating, 22 reviews

Spacious lux home, private pool/spa, 80' dock

HeatherRating, 5 stars1 month ago
The house was exactly how it was described online. Everything was well marked. Lots of stuff to do at the home. Very spacious and well maintained. There were only 7 of us, so lots of extra space. The pool is on the perfect side so your not blasted with the late afternoon sun. However, there is a huge umbrella in case it is needed. Kitchen is fully stocked so nothing was needed. There is a BBQ grill as well as a flat top which is nice for outside cooking. The only thing I would recommend is to bring your own pillow if your a particular pillow person (we love our feather pillows), house pillows were not feather ones. If you rent here and have a boat definitely go to the Sombrero Lighthouse to snorkel. Never saw so many fish in one place. The Conch Cafe and Coast to Coast pizza are both great food restaurants and walkable from the home. Publix is so close it was a daily visit. Truly enjoyed the week stay!!!!!
Superhost
A tiki bar with a thatched roof offers seating along a glass countertop. Two cocktails rest on the counter, with serene water views visible beyond. Boats are docked discreetly along the shoreline, surrounded by greenery and natural light.
Home in Key Colony Beach
4.74 out of 5 average rating, 141 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

MichaelRating, 5 stars3 weeks ago
Great place to stay for family vacation or guys fishing trip. Plenty of dock space to park the boat and easy access to the Atlantic. House is clean and all amenities worked as they should. Would definitely recommend to a family or friend. Mary was a great host who provided all information without even requesting it.
Superhost
The outdoor area features a sandy patio surrounded by palm trees, with several blue Adirondack chairs facing a shaded seating area under a white gazebo. The spacious home stands in the background, showcasing multiple balconies and a light-colored exterior.
Home in Marathon
4.89 out of 5 average rating, 64 reviews

Gorgeous Ocean View Home!

ChristinaRating, 5 stars1 month ago
We had an amazing time with our family and a beautiful Easter dinner with our friends. The location is perfect to travel all of the keys as it's just over an hour to Key West and Key Largo. The sun rose over the top floor guest bedroom with such a beautiful view of the water every day. Morning coffee with the view was awesome. Evenings spent wrapped on the couch watching movies with really nice big TV and unwinding. Sitting down by the water in evenings before sunset hanging with family watching niece play in sand was great too. Highly recommend.
Guest favorite
A private backyard features a hot tub and a shallow pool, surrounded by tropical greenery. Lounge chairs in teal are positioned nearby, and a grill is placed on the concrete patio. The canal is visible in the background, lined with palm trees.
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Waterfront w/pool and hot tub

TanyaRating, 5 stars1 month ago
Rachel’s home is so beautiful and relaxing. The area is perfect. We had such a nice time! My daughter has pet allergies, and she had no issues at all the two days she joined us because it was so spotless and clean.

Beachfront home rentals with a pool

Guest favorite
A fishing dock is depicted with a thatched roof providing shade, surrounded by clear turquoise waters. The wooden platform extends outward, bordered by posts with black caps. The tranquil scene highlights the inviting atmosphere of the waterfront setting.
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Ocean Escape 97

LisaRating, 5 stars1 month ago
Omg what can’t I say about the house. Beautiful! Very friendly neighborhood. Extremely clean and beautifully maintained. The host were available and responded so quickly. We loved it and will be back! Thank you so much for sharing paradise with us!
Guest favorite
A peaceful canal scene is presented with clear blue skies and palm trees lining the water's edge. The calm water reflects the greenery and nearby structures, creating a serene atmosphere. A patterned walkway runs alongside the canal, adding to the tranquil setting.
Home in Marathon
5 out of 5 average rating, 6 reviews

Casa Chiquita Waterfront Home

ShanaeRating, 5 stars1 week ago
My family and I really enjoyed this home the pictures do not do it justice it’s beautiful. The owners are very responsive and we were even able to check in a day early ! The canal was awesome , a boat is a must and so much fun. We saw manatees and iguanas. The private pool was fun all together a great experience.
Top guest favorite
A serene outdoor space features a heated pool surrounded by lush greenery. Brightly colored lounge chairs are arranged invitingly, complemented by colorful throws. A kayak rests by the pool's edge, creating an inviting atmosphere for relaxation and aquatic adventure.
Home in Marathon
5 out of 5 average rating, 51 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

RickRating, 5 stars2 weeks ago
We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!
Superhost
An aerial view displays a resort setting featuring a heated pool surrounded by palm trees, beach cabanas, and lounge chairs. The property extends towards the beach, with picnic tables and a landscaped area visible. The ocean borders the scene, enhancing the tropical atmosphere.
Condo in Islamorada
4.78 out of 5 average rating, 94 reviews

Studio with Balcony, Kitchen, Open Living Space

BenjaminRating, 5 stars1 week ago
My husband and I chose this place for part of our honeymoon, and we were so happy we did! We absolutely loved it, even more than the resort we paid double the price for in Key West. Our room was clean and very comfortable. The pool area was equally clean, never too crowded, and offered a really peaceful atmosphere. Having a full kitchen was a huge benefit for us, it allowed us to save money on meals and enjoy some home-cooked food. We were also incredibly lucky to have a beautiful view of the water from our room. We loved waking up each morning, making breakfast in our kitchen, and eating it on our little patio while enjoying the view. There’s lots of cool stuff to do in Islamorada, and the location of this place made it easy to explore everything. We had such a wonderful experience and would love to return someday!
Top guest favorite
A serene outdoor area showcases a thatched-roof shelter beside calm water. Sun loungers are arranged on a gravel surface, and a table set for two invites relaxation. Lush palm trees provide shade, while the blue water reflects a clear sky dotted with fluffy clouds.
Camper/RV in Key Largo
4.97 out of 5 average rating, 96 reviews

paradise point, ocean front, ramp.

LysandreRating, 5 stars2 weeks ago
Wow! This place is fantastic, beautiful and so calm! We had so much fun , we brought our paddle boards but there was also some kayaks already there, the place is clean, AC works great, lots to see nearby. Emerita was super responsive and very nice!
Top guest favorite
Condo in Marathon
5 out of 5 average rating, 20 reviews

*NEW* Private Beach, pool & fully loaded kitchen

JamesRating, 5 stars1 month ago
Our first time visiting the Keys and Celia’s place made it wonderful! Located in a very nice, quiet, and safe community her condo is like new and so well cared for. Perfect size for our two couples. The decor and furniture is very nice, bright and clean. Had all the amenities we needed and then some. We enjoyed the heated pool everyday and the private beach was nice for a more natural experience. The furnished patio had a great view of the pool and ocean. Celia is a wonderful host! Very helpful and a great communicator.
Guest favorite
A welcoming sign for Skipjack Resort and Marina is prominently displayed, surrounded by lush palm trees and manicured greenery. The blue sky adds a bright backdrop, enhancing the inviting atmosphere of the resort.
Apartment in Marathon
4.85 out of 5 average rating, 27 reviews

Sombrero Beach Tropical Paradise

TriciaRating, 5 stars1 week ago
we had an extremely satisfying stay at skipjacks. the place was incredible. the condo was well kept and easy to access. we loved it.
Guest favorite
A charming two-story residence is set amidst tropical greenery. White fencing and manicured hedges frame the property, highlighting its inviting exterior. Verandas with railings extend from both levels, offering a glimpse of the expansive blue sky and palm trees swaying gently in the breeze.
Home in Marathon
4.92 out of 5 average rating, 26 reviews

Hawk's Hideout

ErikRating, 5 stars3 weeks ago
Travis’s place was perfect and a great home base as we visited the Florida Keys. Great central location from FLL Airport and Key West. Beautiful, peaceful surroundings. Plenty of restaurants within a 15-20 minute drive. Great indoor space and bedrooms with ample outdoor space. A nice little soak/dip pool with outdoor seating. Great front balcony for your morning coffee. Would absolutely stay again and recommend. A++

Private beachfront home rentals

Top guest favorite
The exterior of a charming waterfront home is depicted, showcasing a canal with clear turquoise water. Lush palm trees frame the property, and well-maintained landscaping adds to the serene environment. The two-story building features a spacious porch and multiple balconies, enhancing outdoor living.
Home in Marathon
4.95 out of 5 average rating, 66 reviews

Coral Lagoon #23- Private Villa Home

ReneeRating, 5 stars2 days ago
Wonderful Stay! Place was super clean and nicely decorated with minimal decor. (Sometimes places are over decorated and busy) Beach Towels were provided. Kitchen was organized & clean. Pool was nice! We brought our small dogs and the grounds were very pet friendly. Jessica’s recommended list of restaurants was spot on! Had a great time eating at several of the places. Would visit again and recommend to others.
Superhost
A spacious living area features large glass doors that open to reveal ocean views. The comfortable seating arrangement includes a light-colored sofa and a wooden coffee table. Natural light floods the room, creating a bright and inviting atmosphere. A dining area is visible in the background.
Apartment in Islamorada
5 out of 5 average rating, 3 reviews

Ocean View Duplex Penthouse | Pool | Vista Two

AnneRating, 5 stars2 months ago
Beautiful, very clean property with a fantastic location. Excellent proximity to snorkeling, restaurants and other local attractions. Short stroll to excellent walking path that takes you along route 1 with amazing morning views of the beautiful water. Great views all around, in fact. Plenty of soft, plush towels and similarly luxurious bed linens. We had a wonderful family vacation staying at this property.
Top guest favorite
An aerial view captures a coastal community surrounded by vibrant blue waters and lush greenery. Boating channels meander throughout the area, leading to nearby homes. A mixture of residential properties and docks is visible, indicative of a relaxed tropical lifestyle.
Home in Marathon
5 out of 5 average rating, 41 reviews

Discount Available! 100' Dock, Lots of Amenities!

DanaRating, 5 stars2 weeks ago
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.
Superhost
A modern kitchen features stainless steel appliances and white cabinetry, complemented by a light countertop. A dining area and living space are visible in the background, along with a staircase leading to the upper level. Large sliding doors provide access to an outdoor view.
Condo in Duck Key
4.85 out of 5 average rating, 94 reviews

Villa 5087 on Duck Key BOAT SLIP available

JadenRating, 5 stars3 weeks ago
Great stay, would highly recommend, home was clean and quiet. Can’t wait to come back to duck key so I can book again.
Guest favorite
Palm trees are seen swaying gently in the breeze, framing the entrance to the cottage, which features a welcoming front porch with two wooden chairs. The interior showcases a modern dining area, complete with a chandelier and decorative plants. A plunge pool is visible in the outdoor space, surrounded by tropical greenery.
Home in Marathon
4.94 out of 5 average rating, 90 reviews

Conch Cottage at Hawks Cay - Chic Tropical Retreat

VicenteRating, 5 stars4 weeks ago
Loved it! I hope to go again some day in the near future.
Guest favorite
A charming bungalow with large windows is set against a vibrant blue sky. The exterior features light-colored siding and is surrounded by lush greenery and palm trees. A wooden deck is adorned with chairs and a small table, creating an inviting outdoor space.
Home in Upper Sugarloaf Key
4.94 out of 5 average rating, 95 reviews

Lighthouse - Beach Houses Key West

AlexisRating, 5 stars2 weeks ago
We loved our stay at The Lighthouse! The place was clean, host was responsive, pool area was great, and the ocean was beautiful. While we were in heavy seaweed time, we enjoyed coffee on the deck every morning with beautiful sunrises and water scenes. The pool and BBQ area was amazing!! We grilled almost every night there and had all we needed. We enjoyed having bikes to ride the island! 10/10 stay and we will definitely be back!
Guest favorite
A serene view overlooks the water at sunrise, with soft pastels reflecting on the surface. A white patio table and chairs are positioned under the covered porch, inviting relaxation. The horizon features gentle clouds and distant islands, creating a peaceful atmosphere.
Home in Cudjoe Key
4.91 out of 5 average rating, 34 reviews

Rise And Shine On The Water

FlorianRating, 5 stars3 weeks ago
Wir waren zu fünft im Haus und haben uns sofort wohl gefühlt. Es war alles super sauber. Die Lage direkt am Wasser war wie erwartet überwältigend. Es war alles vorhanden, was gebraucht wird. Die Küche und Terrasse waren sehr groß und die Matratzen waren sehr bequem. Nach Key West fährt man ca. 30 Minuten. Check-in und Check-out sowie Kontaktaufnahme waren völlig unproblematisch. Wir kommen wieder!
Superhost
The property features a private outdoor area with a heated pool and ample seating arranged around a sand area. A deep water dock extends into the turquoise water, while palm trees provide shade. The layout showcases open water views and a welcoming atmosphere.
Home in Marathon
4.88 out of 5 average rating, 17 reviews

P31 - 11785 5th Ave. Ocean

PattiRating, 5 stars2 months ago
I knew that I was limited on what I could do during the week stay bc of a knee injury and it was just fine bc I was quite happy just being at the house for most of my stay. Just loved it and didn’t want to leave. Even though this is an active boating location and boating route l, I still felt quite peaceful staying there. The pool was great and the hot tub was quite beneficial for my knee. Just be careful climbing into the pool. The ladder going up is quite steep. I would’ve preferred some true stairs. But that’s coming from someone with a hurt knee too so take it with a grain of salt. And if you don’t feel like going out to eat, seriously order the steamed shrimp by the pound at FishTails on the corner. It is within walking distance. Will definitely be back for another stay in the future.

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