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Beachfront holiday rentals in Fiesta Key

Find and book unique beachfront homes on Airbnb

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Popular amenities for beachfront rentals in Fiesta Key

Pet-friendly beachfront home rentals

Guest favourite
Guest house 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 favourite
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!
Top guest favourite
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
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
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.
Top guest favourite
Houseboat in Tavernier
4.89 out of 5 average rating, 237 reviews

Florida Keys Luxury Houseboat on the water WiFi

BrandyRating, 5 stars2 weeks ago
The Baycation was amazing! Heidi is an excellent host, she met us at the boat the first night as there are some housekeeping things to go through. It is a boat after all! The space was perfect for the two of us. Great decor and it had everything we needed for cooking our fresh caught fish! We took the paddle boards out to the island and great to see some great wildlife! The Old Tav has the best eggplant parm and the Cuban cafe has amazing coffee and pastries! A bonus for us was getting to meet the local dock kitty, Sasha! 😻 such a sweet girl! It was so cool to sit on the beck deck and watch the mullet, tarpon and barracuda! We highly recommend Heidi’s place!!
Guest favourite
Home in Key Colony Beach
4.95 out of 5 average rating, 20 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

KimberlyRating, 5 stars3 weeks ago
Amazing Stay in the Florida Keys! We had an absolutely incredible time at this home in the Florida Keys! Everything about our stay was perfect. The house was clean, comfortable, and had everything we needed for a relaxing getaway. The highlight was definitely the pool — it was beautiful, well-maintained, and the perfect spot to unwind after a day of exploring. The outdoor space was peaceful and made it feel like our own private paradise. Loved the tv out by the pool! We couldn’t have asked for a better place to stay. The location was great, the home was even better than expected, and we left feeling completely refreshed. Highly recommend and would definitely stay here again!
Guest favourite
Home in Marathon
5 out of 5 average rating, 8 reviews

Azul Paradise - Waterfront - Heated Pool - Dock

CindyRating, 5 stars2 months ago
We really enjoyed our stay here. We loved the pool area and outdoor kitchen and thought the outdoor freezer was just an extra special touch. The house was clean and had plenty of pillows and blankets. The appliances were all new including the washer and dryer and Michael and team were incredibly responsive and kind of we will book here again in the future. The canal is narrow but we did see plenty of fish swim by, especially at night with the neighbors snook light. The kitchen was stocked with everything we needed and there was plenty of plates and glasses for us through the week too. We liked that there were beach towels for us to use as well.

Beachfront home rentals with a pool

Top guest favourite
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.
Superhost
Apartment in Tavernier
4.88 out of 5 average rating, 153 reviews

Reel Large END Unit in Ocean Point Suites

RyanRating, 5 stars1 week ago
The place was as described. Check in was easy and Desy even allowed us to check in a bit early due to my son having a fever. The linens and accommodations were clean and the condo set up was very nicely. The property is close to restaurants and supermarkets. The pool was clean and we enjoyed the area that sold food and drinks by the pool. This was a nice place to unwind after being on the water fishing for 6-8 hours. Very comfortable, private, and peaceful.
Guest favourite
Home in Marathon
5 out of 5 average rating, 6 reviews

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.
Superhost
Apartment in Islamorada
4.64 out of 5 average rating, 28 reviews

Key Life: 1 BR Condo Two Balconies

KevinRating, 5 stars1 week ago
The place was spotless, easy check in, great pool, right on the water and fantastic location. My family and I will definitely stay here again. Cannot say enough about how amazing our trip was.
Top guest favourite
Campervan/Motorhome in Key Largo
4.98 out of 5 average rating, 215 reviews

NEW luxury RV, Marina, 6 beds&1.5 baths, 2 pools!

MarkRating, 5 stars3 weeks ago
First RV experience, did not expect massage sofa... everything you need to explore the mangroves off the beach, take a paddle and who knows what you'll meet...explore the state parks, snorkel, dive kayak fly...it's what you make it ..wish we were here for longer and Kelly is a top host...🤗
Top guest favourite
Campervan/Motorhome 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 favourite
Apartment 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 favourite
Flat in Marathon
4.85 out of 5 average rating, 27 reviews

Sombrero Beach Tropical Paradise Hotel

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.

Private beachfront home rentals

Top guest favourite
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.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 17 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars1 week 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!!
Guest favourite
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Florida Keys Oceanside Utopia

CaroleRating, 5 stars1 month ago
Shane and Kelly were fabulous! My husband and I enjoyed a week away and loved exploring Marathon. Fishing from the back deck was so much fun. We caught some mangrove snapper that we made for dinner which was exquisite! I also caught a Jack Cravalle and my hubby caught a shark. Definitely fun times! Explored beaches, hiked and went to Key West for a day. Weather did not disappoint. Highly recommend this great vacation home!
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.
Superhost
Apartment 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 favourite
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 favourite
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
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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  4. Monroe County
  5. Fiesta Key
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