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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.
Guest favorite
Three colorful adirondack chairs—one red, one yellow, and one green—are positioned on a sandy beach under palm trees. The calm blue water extends towards the horizon, while a rocky wall forms a subtle boundary in the background.
Home in Marathon
4.91 out of 5 average rating, 32 reviews

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

LisaRating, 5 stars2 days ago
Beautiful, well appointed home in the middle of the keys within driving distance to all the tourist attractions and restaurants. We are a 3 generation trip with grandparents and kids, and this house had it all! 3 bedrooms, each with excellent ocean views, great kitchen, kayaks and bikes in the garage, and incredible outdoor seating area! Highly recommended for families.
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 stars1 month 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 stars4 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 vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.
Home in Marathon
4.94 out of 5 average rating, 103 reviews

Coco Plum Waterfront Hideaway Home in Marathon

KyleRating, 5 stars3 weeks ago
Fantastic stay, and a fantastic host! They went out of their way to make sure we had everything we needed for our stay.

Beachfront home rentals with a pool

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 stars2 weeks 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.
Guest favorite
A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

RobinRating, 5 stars2 weeks ago
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didn’t love.❤️
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 stars4 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!
Top guest favorite
A large swimming pool is surrounded by palm trees, creating a tropical atmosphere. The pool features a hot tub integrated into the pool area, with comfortable lounge chairs positioned around it. The sky is clear, and sunlight reflects off the water's surface.
Home in Key Colony Beach
5 out of 5 average rating, 22 reviews

Boat Dock+King Beds & Cabana Club

OliviaRating, 5 stars2 weeks ago
Randall's place was amazing! Exactly what we were looking for - beautiful views of the canal with a dock and views on the other side of the house facing the golf course. The sunrise and sunsets were spectacular here and we loved the beach at the Cabana Club. The bed was also extremely comfortable. Roy and Randall got right back to us with any questions we had. The entire stay was perfect. couldn't have asked for more. Thanks so much!!
Superhost
Condo in Key Colony Beach
4.88 out of 5 average rating, 105 reviews

Beachside Unit 27 - The Beach is Calling You!

MaryRating, 5 stars1 week ago
Cindy’s beachside condo was absolutely perfect! The location couldn’t be better—just 10 steps from the beach. The condo was impeccably clean, peaceful, and quiet, making it ideal for a relaxing getaway. It was the perfect place to celebrate our ten-year anniversary. We couldn’t have asked for more and will definitely be back!
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 stars3 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!
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.
Top guest favorite
A spacious balcony provides views of the ocean and pool area, with comfortable seating arrangements including two chairs and a table. The gentle wave pattern of the sea is visible in the background, along with a poolside and a nearby pier.
Condo in Marathon
4.95 out of 5 average rating, 22 reviews

Ocean Oasis!OceanView-Private Beach/Pool/TikiHuts

VeraRating, 5 stars2 weeks ago
Yuni’s condo was beautiful. It was clean, comfortable and my family of 4 had plenty of room to relax. The kitchen was well- stocked with everything a person would ever need. The location for us was perfect- about an hour drive to Key Largo and a little over an hour to Key West. By staying in the middle key of Marathon, we were not far from any of the keys. The complex was quiet with a small beach and swimming area as well as a pool. There was a lot of seaweed on the beach during our stay but that didn’t bother us- we had a different tour every day - biking, kayaking, and snorkeling. If you want to go to a beach to swim, try Bahia Honda State Park, which is only about 15 minutes away. After all of our activities, we went back to the condo each night for a great night’s sleep. This is a wonderful place to stay away from the hustle and bustle of Key West. You can’t go wrong with Yuni’s condo!

Private beachfront home rentals

Top guest favorite
An aerial view captures the duplex home situated near a canal with multiple boats docked along the water. The vibrant homes are seen in a tangle of greens and blues, with sandy pathways and lush landscaping complementing the serene coastal environment.
Home in Marathon
5 out of 5 average rating, 18 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars2 weeks ago
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!
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 stars4 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
Home in Marathon
5 out of 5 average rating, 3 reviews

KCB Tropical Escape

JosephRating, 5 stars2 months ago
This was better than I expected. A very spacious 2 bedroom with large kitchen, family room. The screened in porch was huge, and a great place to have meals and watch TV and the sunrise. The fully equipped kitchen was awesome for those like us that love to cook. It was a great home away from home. This place was so comfortable and was the best we ever rented.
Top guest favorite
A spacious wooden dock extends over calm waters, featuring a thatched tiki hut and several lounge chairs in a soft blue hue. Lush greenery surrounds the area, complemented by a serene sky at sunset, providing a peaceful atmosphere for relaxation.
Home in Marathon
5 out of 5 average rating, 28 reviews

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

KashRating, 5 stars1 month ago
This property was everything and more. Clean, all amenities provided as advertised and the perfect location in Marathon. Randy was very responsive and went out of his way to provide us with top notch service. We had a wonderful time and will definitely be returning again.
Top guest favorite
A serene swimming pool, featuring a vibrant logo of the Fishing Village at its center, is set against a backdrop of clear blue skies and palm trees. Lounge chairs line the edges of the pool area, offering a tranquil space for relaxation.
Home in Marathon
4.97 out of 5 average rating, 38 reviews

Grouper Getaway @ Ocean Isles Fishing Village

GaryRating, 5 stars1 month ago
Great property, exactly like the photos and descriptions. Ben was extremely proactive and responsive. I would highly recommend this property.
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 stars1 month ago
Loved it! I hope to go again some day in the near future.
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.
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.

Destinations to explore

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  2. United States
  3. Florida
  4. Monroe County
  5. Fiesta Key
  6. Beachfront rentals