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House vacation rentals in Big Pine Key

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Popular amenities for Big Pine Key house rentals

House rentals with a pool

Guest favorite
A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.
Home in Cudjoe Key
4.98 out of 5 average rating, 47 reviews

Waterfront 35’ Dock,80’ pool,20 min Key West

KimberlyRating, 5 stars5 days ago
We had a great stay! House was neat and tidy and in a great location.
Top guest favorite
An aerial view captures a coastal community surrounded by vibrant blue waters and lush greenery. Boating channels meander throughout the area, leading to nearby homes. A mixture of residential properties and docks is visible, indicative of a relaxed tropical lifestyle.
Home in Marathon
5 out of 5 average rating, 41 reviews

Discount Available! 100' Dock, Lots of Amenities!

DanaRating, 5 stars1 week ago
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.
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 stars4 weeks ago
Great property, exactly like the photos and descriptions. Ben was extremely proactive and responsive. I would highly recommend this property.
Superhost
A spacious living area includes a comfortable sofa adorned with decorative pillows, a coffee table, and dining space. Natural light filters through large windows, illuminating contemporary artwork on the walls. The open layout leads to a well-equipped kitchen visible in the background.
Home in Cudjoe Key
4.88 out of 5 average rating, 59 reviews

Cozy 2 br/2 bath home in Cudjoe

MariannRating, 5 stars1 month ago
Marcela's place was exactly as described and very clean. One master bedroom with master bath, and another bedroom with a twin/trundle bed, and sofa in living room. Kitchen had good amenities with cutlery and glasses, etc. We didn't use the washer but the dryer was very handy for drying bath towels and pool towels. We sat outside in the back yard the first night and heard a mysterious animal call, we thought it was a bird but then using google we found out it was a tokay gecko! So cool. We used the large saltwater pool which was very very nice. It's just a short drive to several great restaurants in neighboring keys, and we made a day trip to Key West which was awesome! I recommend Tonio's Seafood Shack & Tiki Bar, great key lime pie. Forks & Stix is a great little sushi place with great lemonade, Island Fish Company in Marathon had a great outdoor vibe right on the water. Best beach is Bahia Honda State Park. Note there is a $125 community fee upon check-in to the resort.
Guest favorite
An outdoor area features a private pool with an adjoining spa, surrounded by lounge chairs. Lush palm trees provide shade, while a spiral staircase leads to the upper level of the house. The setting offers a relaxing space for guests to enjoy.
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars2 weeks ago
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.
Guest favorite
A private pool is surrounded by a lush tropical garden, featuring tall palm trees and vibrant foliage. The clear water of the pool reflects the sunlight, while stone pathways and colorful blooming plants enhance the natural ambiance.
Home in Marathon
4.95 out of 5 average rating, 60 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars2 weeks ago
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!!!
Superhost
Aerial view of the Venture Out community showcases a large swimming pool adjacent to the sandy beach. Palm trees surround the area, with calm turquoise waters extending into the distance. Amenities include a tiki structure and a spacious lounging area, ideal for relaxation and outdoor activities.
Home in Cudjoe Key
4.9 out of 5 average rating, 30 reviews

Waterfront FL Keys Cottage @ Venture Out

MariaRating, 5 stars1 week ago
What a beautiful cottage. Loved how it was decorated. We had everything that we needed. Loved the outside back patio. Peaceful and quiet. The bed was super comfortable. Very clean and a plus, it had a washer and dryer. Thomas and Lindsay were so nice, communicative and very responsive. Gave us some great recommendations on restaurants and things to do in the area. A little piece of paradise. Island Life. We will DEFINITELY be back. Highly recommend.
Top guest favorite
An open living space is featured, highlighted by a round dining table surrounded by comfortable seating. A large television is mounted on the wall, while light-colored walls enhance the bright atmosphere. A serene coastal artwork depicting a pier adds a calming touch to the decor.
Home in Key Colony Beach
5 out of 5 average rating, 18 reviews

Bohemian Beach Bungalow

AnnaRating, 5 stars4 days ago
I can’t say enough great things about this beach bungalow! From the moment we arrived, we were welcomed with warm hospitality and thoughtful touches that made our stay truly special. The bungalow itself is cozy, clean, and beautifully decorated with a laid-back coastal vibe—exactly what you want for a beach getaway. Whether you’re looking for a romantic escape, a solo retreat, or a peaceful base for beach adventures, this place is a gem. We left feeling refreshed and recharged, and we’re already dreaming of coming back!

Weekly house rentals

Guest favorite
A bright living area is showcased with a sectional sofa and a round coffee table. Natural light fills the space, highlighted by decorative lamps and greenery visible through the windows. A woven rug adds texture to the wooden floor, contributing to a relaxed atmosphere.
Home in Marathon
4.96 out of 5 average rating, 23 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

HaleeRating, 5 stars4 days ago
Thank you so much for such an amazing stay! We loved the gorgeous property and all the lovely decor inside! Property was extremely clean and Sandy was so kind and helpful! We spent almost every evening in the hot tub! The home had everything we neded for an awesome week and was in a great central location, close to everything we wanted to do! We loved TJs Tiki Bar for dinner and a beautiful sunset! Thank you again Sandy! :)
Superhost
A vibrant sunset casts warm hues over the water, creating a mirror-like reflection. A wooden dock extends into the foreground, leading to the horizon, surrounded by silhouettes of trees along the shoreline. Outdoor seating is visible near the water's edge.
Home in Summerland Key
4.58 out of 5 average rating, 84 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

SarahiRating, 5 stars1 month ago
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.
Top guest favorite
A private pool is situated beside a spacious deck, surrounded by tropical plants and palm trees. Comfortable lounge chairs are placed near the pool, and stairs lead to the upper level of the stilted structure. The area offers direct access to the canal.
Home in Marathon
5 out of 5 average rating, 14 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

BradleyRating, 5 stars2 weeks ago
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!
Top guest favorite
A boat is docked beside a light blue cottage, featuring large windows that reflect on the water's surface. Lush palm trees surround the property, enhancing the tropical atmosphere and offering a serene view of the canal.
Home in Marathon
4.98 out of 5 average rating, 47 reviews

Flamingo Palms-Spring discounts-NOW available

LaurenceRating, 5 stars1 month ago
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
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 scenic view of a calm waterway, featuring a thatched-roof hut on a dock and several palm trees. A second dock with covered areas can be seen in the distance under clear blue skies, creating a relaxing waterfront setting.
Home in Cudjoe Key
4.86 out of 5 average rating, 43 reviews

Relaxing and Inviting home with 35' dock

MichelleRating, 5 stars1 month ago
The place was small and cozy fit our family of five, just 30 minutes from Key West and about 30 minutes from Marathon. Venture Out has a heated pool, heated kids pool, and hot tub as well as a Lagoon to swim in. . Lots of amenities in the rec room as well as tennis courts, pickle ball, and a small playground . There are nearby restaurants. Location was great!
Guest favorite
A sandy beachfront is framed by palm trees, with the glistening Atlantic ocean in the background. A volleyball net is set up on the sand, along with multiple seating areas for relaxation, inviting guests to enjoy the tranquil environment and scenic views.
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars1 week ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.
Guest favorite
A private deck overlooks lush greenery leading to the ocean. A circular table with six chairs sits under a large umbrella, providing a shaded spot. The scene features bright blue skies and a calm sea, creating a serene atmosphere.
Home in Marathon
5 out of 5 average rating, 53 reviews

Oceanview Escape

JoshuaRating, 5 stars2 months ago
Rachel has put a lot of care and thought into hosting! Her place was great, and Rachel was always very responsive! The location is wonderful — quiet, near Sombrero beach, and centrally located in Marathon. Grocery stores and restaurants nearby. Good guide book recommendations! Amenities were great! We would definitely stay again.

Private house rentals

Guest favorite
An inviting open living area is featured with comfortable seating options, including a large blue sofa and patterned chairs. A flat screen TV is positioned on a wicker stand. A staircase leads to the second floor, and a dining area with a round table and rattan chairs is visible.
Home in Cudjoe Key
5 out of 5 average rating, 16 reviews

Keysie Does It at Cudjoe Key

MeganRating, 5 stars3 months ago
We absolutely loved our stay! Our checkin was smooth and flexible. The home was squeaky clean, linens and beds were unbelievably soft and comfortable, and there were more supplies/ amenities in the home than listed. We felt right at home and would love to come back! Absolutely 5 star place!
Top guest favorite
A serene outdoor area features a heated pool surrounded by lush greenery and palm trees. Two chaise loungers sit on a small patch of grass, offering a perfect spot for relaxation. The ocean is visible beyond the white fence, enhancing the tranquil setting.
Home in Marathon
5 out of 5 average rating, 38 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

JillRating, 5 stars1 month ago
If I could rate this stay a 20, I would. We came across the listing last June, after wanting to try something different on our annual trip to Marathon. It looked perfect for our family. What I didn’t expect when we arrived on April 16, 2025, was to be blown away. The pictures don’t do it justice. The house is STUNNING. I felt like we were walking in/staying at a brand new house as the very first guests. The colors, the furnishings, the level of coziness brought to this luxury beach house was unmatched. The towels (bath and beach) were plush and soft. Pool speakers. The bar! I mean everything. The kitchen was stocked with what you need - high end gadgets, utensils that actually work, and every pot and pan (organized). Immaculately cleaned. And then the views. Holy guacamole. My dad parked himself on the main floor deck and didn’t move for seven days. Airbnb was right- RARE FIND. Amanda - you are the hostiest host in the world. Your communication was 💯. And we pray to make it back to yo
Top guest favorite
A serene outdoor space features a private pool surrounded by stone decking. Two lounge chairs with blue cushions are positioned nearby, while a tiki hut adds a tropical touch. Lush palm trees and a canal lined with vegetation provide a tranquil backdrop.
Home in Marathon
4.98 out of 5 average rating, 60 reviews

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

NickRating, 5 stars1 month ago
The place was perfect for our needs. Pool, tiki hut, and canal were great. The beds were comfy as well. Daileny was quick to respond and accommodating.
Guest favorite
An aerial view captures the oceanfront estate featuring a spacious house with a light green roof. A private pool is surrounded by lounge chairs, while kayaks rest on the sandy area by the water. A long pier extends into the clear, shallow water, framed by palm trees.
Home in Marathon
4.96 out of 5 average rating, 26 reviews

Million Dollar View

JohnRating, 5 stars1 month ago
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.
Superhost
A serene waterway is shown, flanked by palm trees and waterfront homes. A boat is seen navigating the calm waters, with clear skies enhancing the tranquil scene. The reflection of the surroundings is visible on the surface, creating a peaceful atmosphere.
Home in Cudjoe Key
4.62 out of 5 average rating, 165 reviews

Ocean Front Home in Great Location

MichaelRating, 5 stars1 month ago
Fantastic place for a home base while the beautiful keys. Close enough to key west for an upbeat day, very quiet in the evening. If anything, I’d say I was expecting less from the description and was very surprised at how nice this place is. I would stay here again in a heartbeat!
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 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.
Top guest favorite
A private pool is framed by a well-maintained lawn and patio area. Umbrellas provide shade for seating, while a tranquil canal with boats is visible in the background, enhancing the serene outdoor environment.
Home in Key Colony Beach
5 out of 5 average rating, 84 reviews

“La casa azul” step 3’ to a private pool

RickRating, 5 stars1 week ago
We spent an amazing week in this home. Very comfortable and quiet. The pool was amazing. Will definitely be back.
Guest favorite
A private backyard features a hot tub and a shallow pool, surrounded by tropical greenery. Lounge chairs in teal are positioned nearby, and a grill is placed on the concrete patio. The canal is visible in the background, lined with palm trees.
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Waterfront w/pool and hot tub

TanyaRating, 5 stars1 month ago
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.

Quick stats about house rentals in Big Pine Key

  • Total rentals

    170 properties

  • Nightly prices starting at

    G$12,553 GYD before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    60 properties have a pool

Destinations to explore

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