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 stars1 week ago
We had a great stay! House was neat and tidy and in a great location.
Top guest favorite
An outdoor space features a sparkling in-ground pool surrounded by a sun deck with several lounge chairs. A shaded screened-in porch is visible in the background, along with a gas grill and a cornhole game set nearby. Lush palm trees provide a tropical atmosphere.
Home in Marathon
4.99 out of 5 average rating, 137 reviews

Cancellation Deal: 08/02 thru 08/09

KevinRating, 5 stars1 week ago
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie
Top guest favorite
An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars2 weeks ago
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.
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
4.88 out of 5 average rating, 32 reviews

Waterfront FL Keys Cottage @ Venture Out

ElizabethRating, 5 stars1 week ago
Great location, easy access to everything, lots of amenities on the community.
Top guest favorite
A serene outdoor pool is surrounded by lounge chairs and umbrellas, with palm trees swaying gently nearby. The expansive water reflects the clear blue sky, while the ocean can be seen in the background, enhancing the inviting atmosphere for relaxation.
Home in Key Colony Beach
4.98 out of 5 average rating, 106 reviews

Waterfront House with 37 ft Dock & Cabana Club

CaseyRating, 5 stars5 days ago
Enjoyed the stay! If you’re looking for a low key place to stay this is it. Great location for day adventures in the keys.
Guest favorite
A bright living area features a green sofa adorned with decorative cushions, flanked by two woven ottomans. Natural light filters through the white curtains, while a large television and colorful wall art enhance the space. Rattan accents and indoor plants bring a refreshing touch.
Home in Cudjoe Key
4.93 out of 5 average rating, 60 reviews

Betty's Place

EmilyRating, 5 stars2 weeks ago
Honestly I was super impressed with how quick Jacqueline responded and how smooth the check in went. Betty’s Place was such a beautiful home and very clean and spacious. We had an amazing time and can’t wait to plan another keys trip at Betty’s place!
Guest favorite
Home in Marathon
4.97 out of 5 average rating, 149 reviews

Marathon one-level home on the Marina - with slip!

BillieRating, 5 stars1 month ago
It was a very nice. The front porch sunrises were amazing. My family enjoyed the accommodations. The pool was fantastic and not crowded. The resort was quiet except for an occassional boat and landscapers.
Superhost
A large swimming pool is surrounded by palm trees and lounge chairs. A hot tub is positioned at the forefront of the image, with bubbling water. Clear blue skies and a sunny atmosphere suggest a relaxing outdoor environment.
Home in Key Colony Beach
4.91 out of 5 average rating, 140 reviews

Tiki Time 2

WarrenRating, 5 stars3 weeks ago
It was a great place inside and out. We had drinks under the tiki hut where it was cooled by the tropical breeze. Being on the ground floor, we seniors never had to climb stairs and the grounds were very even. The dock area was in fair shape but watch out for the small coconuts dropping from the palm trees. The laundry room was good and the machines were very clean and large capacity. The barbecue grill was ok, but the propane unit was rusty and the flames were very inconsistent. We enjoyed ourselves at the Cabana Club where the pool was great and the food there was the best for lunches and drinks

Weekly house rentals

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
Guest favorite
An outdoor seating area features a sectional sofa and high-top bar stools with a view of the water. A peaceful ambiance is created by the surrounding palm trees and the gentle waves of Vaca Cut. Laundry facilities are visible on the left side of the image.
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
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
4.59 out of 5 average rating, 85 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.
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.
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 stars3 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
An aerial view showcases a private dock with a boat alongside a heated pool. Lounge chairs are positioned near the pool, complemented by vibrant palm trees and neatly arranged outdoor furniture. The tranquil waters reflect the bright surroundings, enhancing the overall relaxing atmosphere.
Home in Key Colony Beach
4.94 out of 5 average rating, 16 reviews

Paradise Cove!30ft Dock Pool BBQ

BryceRating, 5 stars1 month ago
Had a great week at Yunis place! Her house was extremely clean and had everything we needed and more especially for cooking which was nice. She had probably the most comfortable bed, sheets and pillows I’ve ever used. I loved how it was clutter free and didn’t have any breakable decorations down low around since we had our two toddlers with us. The pool was the perfect size for us and it was great to relax outdoors. We even saw Manatees swim up to the dock. 10/10 would recommend this spot.
Guest favorite
A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

RobinRating, 5 stars2 weeks ago
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.❤️

Private house rentals

Top guest favorite
An aerial view captures the duplex home situated near a canal with multiple boats docked along the water. The vibrant homes are seen in a tangle of greens and blues, with sandy pathways and lush landscaping complementing the serene coastal environment.
Home in Marathon
5 out of 5 average rating, 18 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars2 weeks 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 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!
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, 24 reviews

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

HaleeRating, 5 stars1 week 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! :)
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 stars3 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!
Guest favorite
A private pool and spa are framed by tropical palm trees, with a serene canal visible beyond. The scene captures bright blue skies and lush greenery, emphasizing the outdoor oasis. Lounge chairs are positioned nearby for relaxation.
Home in Marathon
5 out of 5 average rating, 15 reviews

Waterfront 2-bedroom Home w/Pool and Spa

ChrisRating, 5 stars6 months ago
Great place! Exactly like the pictures. AMAZING heated pool! Very clean. Ruth was an excellent host! She had fresh flowers, toiletries and even snacks and breakfast items to get us started! Most Airbnb’s you have to provide your own TP, paper towels, trash bags and soap but not here! Ruth had the place very well stocked. We will definitely be returning! Thanks for a memorable Thanksgiving week Ruth!!
Superhost
A vibrant green house is presented with large windows adorned with yellow shutters. A spacious front porch is bordered by tropical plants, while a gravel pathway leads to the entrance. Nearby, a blue trash bin is visible, along with a parked vehicle.
Home in Cudjoe Key
4.79 out of 5 average rating, 19 reviews

Tropical Island Getaway

DebraRating, 5 stars2 months ago
Place was sweet, kitchen and bathroom well stocked. We didn’t get an opportunity to try the pool or hot tub. 20 minutes to Key West!! We would stay there again.
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 stars2 weeks ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.
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 stars2 weeks ago
We spent an amazing week in this home. Very comfortable and quiet. The pool was amazing. Will definitely be back.

Quick stats about house rentals in Big Pine Key

  • Total rentals

    170 properties

  • Nightly prices starting at

    R1,084 ZAR 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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