
Beachfront holiday rental in Big Pine Key
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Top-rated beachfront accommodation in Big Pine Key
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Big Pine Key beachfront rentals
Pet-friendly beachfront home rentals

Turtle Cove Views at Venture Out
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
We had a great long weekend at Alex house! You are provided with a starter kit, so you may need to buy extra supplies if planning to stay in at property. House vibes are very keywest. Winn Dixie very close and Bahia Honda state park was close by and beautiful to spend the day if looking for something to do. Keywest about 40 min drive, easy to get around. Had plenty of blankets, pillows and accommodated 10 of us— we did bring an air mattress which I would recommend as sofa beds are not the most comfortable. Has a beautiful backyard which we spent a lot of time on and yummy walkable restaurant. Plenty of parking. Host was very responsive and checked in with us to make sure check in was smooth.

Beachfront Villa - Florida Keys
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!

Luxury Boating Paradise+Pool+Sailing Kayaks
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!

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach
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.

Waterfront w/pool and hot tub
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.

Gorgeous Ocean View Home!
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.

Vibrant Beachfront Villa
Maidelin’s beach villa was exactly what our small family needed for a quick getaway.
Beachfront home rentals with a pool

Waterfront 35’ Dock,80’ pool,20 min Key West
We had a great stay! House was neat and tidy and in a great location.

Grouper Getaway @ Ocean Isles Fishing Village
Great property, exactly like the photos and descriptions. Ben was extremely proactive and responsive. I would highly recommend this property.

Ocean Escape 97
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!

Beautiful Beachfront Villa w/ Pool/Tiki/Dock
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.❤️

#1 Island Hideaway 89 - OCEAN FRONT
It was the perfect location that we wanted away from a high tourist area. The neighbors were very nice and welcoming. Everything was clean and beautiful. I would stay here again! It was perfect for us exploring both the southern and northern keys and beaches since it's about middle of the 2. Loved it!

Beach House, Private Pool & Dock, Gulf Sunset view
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!

Stunning* New* Home Pool in Ocean Breeze Marathon
Susan’s place was exactly as described. The water view from the top deck was a wonderful place to have my cup of coffee every morning. I would highly recommend this place.

Beautiful Cottage & Amenities in Gated Community
Beautiful and well maintained unit within the Venture Out gated community on Cudjoe Key. Spacious with two full bathrooms. The kitchen has everything you need for cooking including pots, pans, and dishes. Plenty of clean linens and blankets available too. The washer and dryer was a great feature as well. Extremely responsive host who answered any questions within minutes ensuring there was never a problem. This was a terrific home away from home. Fairly priced for the community and the high end property that Marcello keeps in pristine state. Highly recommended.
Private beachfront home rentals

Florida Keys Oceanside Utopia
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!

A slice of paradise in the Florida Keys
Wonderful night! Only a few bugs around dusk that left by nightfall. Lots of planes took off from 5-7 PM, but again they stopped by nighttime and not sure that it happens every day. The boat itself was perfect, exactly as described!

KCB Tropical Escape
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.

Conch Cottage at Hawks Cay - Chic Tropical Retreat
Loved it! I hope to go again some day in the near future.

P36 - Charming and immaculate 2 Bedroom, 2 bathroo
Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!

Moana Hale Paradise #164 - Venture Out, Cudjoe Key
It’s awesome. The additional fees are worth it. The community is great and the commitment to keeping the neighborhood classy is excellent.

Sunset Views, Pool and Dock
Thank you Frank for a great place to stay! Close to restaurants, quite neighborhood, nice pool, a dock to swim and fish from, and beautiful sunsets. We had everything we needed.

Flamingo Palms-Spring discounts-NOW available
Excellent host and great home and location. Fishing from the dock, grill on the patio. Lovely decor throughout the property. Made for an excellent choice for my wife’s milestone birthday celebration and Ramon and Ana made that extra special with a birthday banner. Would visit again travel plans permitting
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