Vacation rentals in Fleming Key

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Other great vacation rentals in Fleming Key

Guest favorite
A balcony area is visible, featuring a view of lush greenery and a pool in the background. A comfortable seating arrangement is positioned on the wooden deck, while light filters through the leaves, creating a serene atmosphere.
Apartment in Key West
5 out of 5 average rating, 6 reviews

Casa Caribe 2bed2bath sleeps 6 beautiful decorated

Norma (Jezrael)Rating, 5 stars1 month ago
Judy’s place was one of my favorite we’ve stayed at. She was extremely responsive and helpful. She went above and beyond to accommodate us and we couldn’t be more grateful. Thank you for making our trip so wonderful Judy!
Superhost
A community pool area is depicted, featuring a clear blue pool surrounded by a sun deck. Lounge chairs are positioned nearby, and colorful Adirondack chairs line the railing, providing a view over the water under a bright blue sky with scattered clouds.
Home in Cudjoe Key
4.91 out of 5 average rating, 110 reviews

Sunrise Beach Escape

KimberlyRating, 5 stars1 month ago
The place was really nice. One thing that I didn't like was that the beach really wasn't a beach and to get to the water there was just a little walkway and trying to get the kayak down to the water it was a little hard. The pool needs more lights, so it is easier to see. Also, we had a really hard time with the TV's getting them to work. The king size bed was really comfortable. There were lots to see and do and the place really wasn't too far from Key West so not a bad drive.
Guest favorite
A private pool is surrounded by a spacious deck featuring lounge chairs and a wooden table. Palm trees gently sway in the breeze, while the ocean sparkles in the background, creating a serene setting for relaxation and enjoyment.
Guesthouse in Marathon
4.95 out of 5 average rating, 21 reviews

The Pink Dolphin House.

PatrickRating, 5 stars2 weeks 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
A wooden dock extends into clear turquoise waters, providing access to the surrounding landscape. Lush greenery and palm trees frame the serene view, while a brightly colored patio umbrella adds a pop of color nearby. The peaceful atmosphere is enhanced by the open sky above.
Villa in Marathon
4.95 out of 5 average rating, 135 reviews

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

GregRating, 5 stars4 days ago
This was the perfect space for our family of seven. Cleanliness and all the creature comforts were fully up to our expectations. The interactions we had with Dennis were quick, attentive and friendly. Highly recommend!
Top 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, 176 reviews

Beachfront Villa - Florida Keys

ErinRating, 5 stars1 week ago
This is a fantastic property! Right across from Sombrero Beach but still peaceful and private. The house and yard is like an oasis. Host and management company are WONDERFUL! Highly recommend!
Superhost
Home in Marathon
4.6 out of 5 average rating, 5 reviews

Coastal Paradise: 5-Bed Retreat

TrishRating, 5 stars2 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 favorite
A private pool with lounge chairs is set against a backdrop of palm trees and a tranquil canal. The clear blue sky is scattered with clouds, reflecting the serene atmosphere of the outdoor space. The surrounding area features stone pathways and lush greenery.
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!!!

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Fleming Key