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Holiday houses in Big Pine Key

Find and book unique accommodation on Airbnb

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Popular amenities for Big Pine Key holiday rentals

Stay near Big Pine Key's top sights

No Name Pub54 locals recommend
Boondocks Grille and Draft House and Miniature Golf50 locals recommend
Looe Key Reef Resort & Dive Center33 locals recommend
Kiki's Sandbar Bar & Grille28 locals recommend
National Key Deer Refuge24 locals recommend
Big Pine Rooster16 locals recommend

Other great holiday rentals in Big Pine Key

Guest favourite
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 favourite
Apartment in Key West
5 out of 5 average rating, 7 reviews

Casa Caribe 2bed2bath sleeps 6 beautiful decorated

Robert JoeyRating, 5 stars6 days ago
The condo was great! Clean and decorated tastefully. It was priced fairly and only 5 miles from downtown. Grocery stores and shopping was nearby. The only negative was a few blocks east of the condo were some trashy trailer court neighborhoods that I would avoid on the way to the Hogfish Grill (good food). Otherwise we felt safe.
Guest favourite
Dome in Marathon
5 out of 5 average rating, 7 reviews

Your vacation Dome is here!

JrRating, 5 stars1 month ago
sylvia's property has been a dream come true loved every single part of it beautiful arquitecture, one of a kind sylvia is the kindest human being ever, very polite and helpful all items in house where described as onsite this is the perfect vacation home to book to sumarize in just one word... outstanding thank you very much
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Villa Casa Cayo

AmyRating, 5 stars3 months ago
This home was just what my family needed for our vacation! We all loved relaxing in the outdoor living room surrounded by greenery. We also enjoyed swimming in the pool and kayaking through the canals and Boot Key. We made most of our meals due to dietary restrictions, and the kitchen here was adequate. The location in Marathon is excellent! It was just a 5-minute walk to Sombrero Beach, so we never had to worry about parking. We could easily drive to all the activities we wanted to do in the area, too.
Guest favourite
Villa in Marathon
4.95 out of 5 average rating, 136 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

StefanieRating, 5 stars2 weeks ago
My family and I stayed for a week and the house had everything we needed and more! The space was clean, comfortable and had lots of extras for the outside like pool floats, bikes, paddle boards, kayaks and more. The added touches inside like dish soap, hand soap, cleaning supplies, shampoo and conditioner was unexpected and a huge help. I was slightly surprised that this was an attached home, but there was still plenty of privacy and the location was extremely convenient. The hosts were very friendly and responsive and we would definitely recommend to others.
Superhost
Home in Marathon
4.6 out of 5 average rating, 5 reviews

Coastal Paradise: 5-Bed Retreat

TrishRating, 5 stars3 weeks ago
We loved our latest stay in Marathon. We traveled with two families (2 teens, 2 older children). The house layout was perfect for our group. It was nice to have the kitchenette downstairs by the patio slider for pool snacks (small microwave) and clean-up from beach days/pool days. The beds were all newer, stylist beach decor, & ample space. There is lots of indoor and outdoor (covered and uncovered) table/conversation seating. The pool and hot tub were great. We spent many nights in the hot tub looking at the stars and relaxing. Although, you on a canal with other houses, it’s very quiet. The canal had fish, sharks, and even a cute manatee that visited in the morning. Our kids loved fishing daily. As for location, it’s perfect. You’re only a few miles from Sombero Beach, Sunset Beach, and 7 mile bridge. Publix, bait shops, restaurants all within a short drive. You cannot walk to beaches, but we didn’t mind this. There is a bike trail on Aviation Rd. Near the house.
Superhost
Home in Marathon
4.75 out of 5 average rating, 4 reviews

SeaEsta! Bring your boat & 1 block to the beach!

KellyRating, 5 stars1 month ago
Our stay at John's place was amazing. The location was perfect as we went up and down the Keys spending time in Islamorada and a day in Key West. We walked the neighborhood and to Sombrero Beach. The set up for our boat was fabulous. We were able to leave it in the water to use everyday. The best part of John's house was the outdoor area in back. We stayed out there more than anywhere, of course the weather was perfect. Thank you for sharing your place with us John. We hope to be back!
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 10 reviews

Sleeps 8, 3 bedroom, 4 full bath, pool, 37.5' dock

JeffreyRating, 5 stars7 months ago
Excellent location in a quiet upscale neighborhood. The house was like new, everything was clean and fresh. Very well equipped kitchen and baths. Lots of space indoors and out, with a beautiful small pool! Would definitely recommend this property for a peaceful getaway in the heart of the Florida Keys!!!

Quick stats about holiday rentals in Big Pine Key

  • Total rentals

    260 properties

  • Nightly prices starting at

    $78 AUD before taxes and fees

  • Total number of reviews

    4.9K reviews

  • Family-friendly rentals

    190 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    130 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Big Pine Key