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Beachfront vacation rentals in Big Pine Key

Find and book unique beachfront homes on Airbnb

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Top guest favorite
A zero gravity electric recliner is positioned near a large glass door that opens to a balcony with an ocean view. Colorful artwork featuring tropical fish adorns the wall above, while natural light brightens the spacious room.
Condo in Tavernier
4.96 out of 5 average rating, 186 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

G DRating, 5 stars2 weeks ago
Lucimar was a perfect host. Very responsive with both advice on the area, as well as anything specific we might need or have questions about regarding the condo. The place was very clean and well-maintained. If you happen to self-charter a rental boat for multiple days, we recommend arranging a guest slip at the Ocean Pointe marina. It may coming and going quite easy on our water days. The channel to OP is small and shallow, but well marked with day beacons. Easy to find and see. Take the long way around Tavernier Key, or you may pay a price (shallow flats). On that note, get the prop and skeg insurance, it takes a load off the mind when boating around here. Good electronics are a must for a newbie in these waters (in our view).

Popular amenities for Big Pine Key beachfront rentals

Pet-friendly beachfront home rentals

Superhost
Home in Marathon
5 out of 5 average rating, 4 reviews

Happy Tingler With Pool Tiki and 100 ft of Dockage

LoriRating, 5 stars10 months ago
The location was amazing! We were able to get out to the ocean in minutes. Manatees & iguanas came to visit us often at the house. We really enjoyed this stay!
Guest favorite
The exterior of the beach house is showcased, featuring a bright white facade and a unique geometric design on the railings. A spacious outdoor area is visible, adorned with lounge chairs and a shaded patio table, surrounded by crushed white stone and greenery.
Home in Marathon
5 out of 5 average rating, 17 reviews

Seaside Sunrise. Newly remodeled waterfront

JonathynRating, 5 stars1 month ago
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.
Top guest favorite
Home in Marathon
4.89 out of 5 average rating, 37 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

LydiaRating, 5 stars8 months ago
We booked this home last minute and now have our go-to vacation spot in Marathon! Alida is a friendly host with great communication. The home is very clean. Beds are very comfortable. Kitchen is well stocked with pots, pans, etc. The kayaks and paddle board made our vacation even more special! The steet is very quiet and peaceful. The setting in the back yard is very private, as is the long dock. We had a 23' rental boat for our stay. The view is amazing and the sunsets are a special treat each evening. I very much appreciated the ample, comfortable seating everywhere - inside and outside of the home. Thank you Alida. We made great family memories here!
Superhost
A bright sleeping area features a spacious bed with a light-colored comforter. Two lamps provide soft lighting beside the bed. A desk with a wicker chair is positioned near a window, and an arched balcony door leads to a view outside, framed by light curtains.
Condo in Marathon
5 out of 5 average rating, 3 reviews

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants

MichaelneuroRating, 5 stars4 months ago
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.
Guest favorite
A sandy shoreline is bordered by swaying palm trees, providing a peaceful oceanfront view. A yellow kayak rests on the beach, while a hammock is visible nearby, adding to the tranquil setting. The distant jetty extends into the calm sea, enhancing the serene atmosphere.
Guesthouse in Marathon
4.95 out of 5 average rating, 21 reviews

The Pink Dolphin House.

PatrickRating, 5 stars4 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
The exterior of the vacation home is framed by vibrant palm trees, providing a tropical feel. A white staircase leads to the covered front porch, which features a round glass door. Decorative stone landscaping complements the structure, enhancing its inviting appearance.
Home in Cudjoe Key
4.94 out of 5 average rating, 47 reviews

Private Ocean Oasis by Key West, Florida

JeremyRating, 5 stars1 week ago
Awesome place , well described in a perfect location . The amenities in the resort were awesome, lots to do. Ronda was very responsive with my questions I had about the area and things to do thru out. Will definitely be rebooking with her in the near future. Thanks again Ronda!
Guest favorite
A spacious bedroom is highlighted by a comfortable wooden bed with patterned linens. A bedside lamp casts a warm glow. Floor-to-ceiling windows offer views of the beach, with outdoor seating visible on the patio. Tropical decor adds a subtle touch of elegance.
Home in Marathon
4.9 out of 5 average rating, 29 reviews

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club

SarahRating, 5 stars1 week ago
Our family of 8 stayed for a week and found the accommodations absolutely perfect. The beds were comfortable and clean. I loved the ceiling fans and feeling the ocean breeze through the sliding screen door at night. Plenty of closet space to unpack and the outdoor living area was a dream. We played shuffleboard and grilled out a lot. Excellent lounge chairs made stargazing a delight. Great shower pressure and plenty of towels provided. Washer and dryer worked well, as did all of the kitchen appliances. Only 3 out of the 4 bikes were useable; one of them needs a tune up; handlebars were loose and made riding unsafe. Be warned there are no bike helmets. We didn’t use the paddle boards or kayaks because it was a very windy week and the current was strong but they looked to be in good repair and there were multiple life jackets and water shoes and pool noodles available. Loved the pool and beach access at the clubhouse!
Superhost
Home in Key Colony Beach
4.74 out of 5 average rating, 138 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

DonnaRating, 5 stars1 day ago
The four of us arrived at Mary’s place and we immediately felt right at home. The place was neat and clean and the decor was tropical. The backyard overlooking the canal was a great place to relax and unwind. We loved walking down the block to the Cabana club each afternoon after coming back from local excursions. One of the great benefits was being able to use the Cabana club which had a fantastic pool, hot tub, beach access and a full service bar with great food and drinks with excellent service and a friendly staff!

Beachfront home rentals with a pool

Superhost
A light blue house is prominently featured, elevated above ground level with a staircase leading to the entrance. Palm trees surround the property, creating a tropical ambiance. Nearby homes display a mixture of colors, enhancing the neighborhood's coastal charm.
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Sombrero Beach Getaway

SteveRating, 5 stars1 month ago
We enjoyed our stay very much. He was always very responsive and took care of anything we needed. Might be coming back another time in the future.
Superhost
A private balcony is furnished with a glass-top table and woven chairs, offering a serene view of palm trees and a sandy beach area. The calm water reflects a clear sky, creating a peaceful atmosphere for relaxation.
Home in Marathon
4.69 out of 5 average rating, 16 reviews

#7 Waterfront 4Bed 3Bath Pool Home

CarolRating, 5 stars11 months ago
Location, location, location! Great views, nice pool area, dock space if needed. Walkable to several resorts and turtle sanctuary.
Superhost
A heated saltwater pool is set on a spacious deck, surrounded by lounge chairs. Adjacent to the pool, a serene canal view features lush greenery and residential homes lining the waterway.
Home in Marathon
4.91 out of 5 average rating, 23 reviews

4BR Sombrero Beach House on Canal with Dock & Pool

DianeRating, 5 stars2 weeks ago
We thoroughly enjoyed our week at Matt’s place! As a host, Matt was quick to answer our questions and provide what we needed. The location is excellent, with the canal views from the back yard and a few minutes walk to the beach.
Superhost
A serene outdoor space features a heated pool adjacent to a relaxing spa, framed by swaying palm trees. Sun loungers sit beside the water, while the distant dock and lush landscaping create a tranquil ambiance.
Home in Marathon
4.94 out of 5 average rating, 16 reviews

Pool & Spa, Walk to Beach, Dock, Tiki, Lux Home

Stefan And KarenRating, 5 stars2 weeks ago
The house was spacious and clean, and we got good use out of the pool and hot tub. Bert requires signing a separate contract after booking on AirBnB, but worked with us to tailor the language. Towels are provided but be prepared to bring most other amenities like shampoo, etc yourself. Also, be aware that Sunrise Drive is a private road and you cannot access the beach there - Sombrero Beach is about a 15 minute walk, but definitely worth the walk!
Superhost
A scenic pool area is visible, featuring a hot tub adjacent to the water's edge. Palm trees sway gently in the breeze, providing a tropical atmosphere. The blue sky reflects on the tranquil water, enhancing the serene setting.
Home in Marathon
4.75 out of 5 average rating, 24 reviews

Sunset Views, Pool and Dock

JamesRating, 5 stars2 weeks ago
We stayed at Frank’s place for two weeks and had an absolutely amazing time! The house was spotless, well-equipped, and super practical for our two energetic little ones. The pool and hot tub were perfect. We made the most of every sunset soaking in the hot tub, followed by peaceful late-night floats in the pool under clear, starry skies. We fished off the jetty most days and caught barracuda, mangrove snapper, plenty of sharks—and the neighbors even hooked a tarpon and landed a grouper! The kids loved snorkeling right off the dock, spotting rays, turtles, and loads of colorful fish. We missed the manatees when they came by one morning, but luckily caught up with them later while kayaking through the mangroves. Huge thanks to Frank for being such a fantastic host. One day we had a small issue with the pool, and his team showed up in under 10—absolutely amazing service. We truly didn’t want to leave and would come back in a heartbeat. Highly recommended!
Superhost
Home in Key West
4.6 out of 5 average rating, 5 reviews

Coastal Comfort; Waterfront Luxury Home with priva

JayRating, 5 stars18 months ago
We all loved the house. Plenty of space, the outdoor patios were a daily hangout, the views were great, what's not to love. The maintenance of the house itself was excellent and it didn't feel like a "rental". Well decorated, not worn down, a bathroom for everyone, it was great. We rented a golf cart to get back and forth from town which was very easy and barely a ten minute drive. We did have a small issue with the pool while there, which apparently is very unusual. It is Key West so it took a few days to get the parts needed. However, Javier was always easy to reach and while he did eventually fix it it was his 'out of the box' thinking and communication on everything that was superbly professional. I understand he manages several properties and we would gladly stay at any of them. With an AirBNB, if something goes wrong and you're far from home all you have to rely on is the owner/manager and you are in excellent hands with Javier. A++ on customer service
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars3 months ago
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.
Guest favorite
A tranquil pool area features a clear blue pool surrounded by paved decking. Colorful lounge chairs are positioned nearby, with a thatched-roof cabana offering shaded seating. The expansive view of the Atlantic Ocean is visible beyond the pool area, complemented by a bright sky.
Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviews

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

JessicaRating, 5 stars1 month ago
If you are looking for a relaxing and peaceful location, this is the place! John was so helpful! The place was exactly as described. Our family felt right at home and enjoyed being away from the busyness of larger keys! Close to Key West and some amazing restaurants!

Private beachfront home rentals

Guest favorite
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.
Superhost
A spacious bedroom features a large bed with a textured white coverlet. Framed fish artworks hang above the bed, complemented by two bedside lamps. A white sectional sofa is positioned against the wall, and natural light filters through the window with wooden shutters.
Guest suite in Key Largo
4.9 out of 5 average rating, 154 reviews

Oceanside Bungalow in Key Largo

AnnalieseRating, 5 stars2 weeks ago
Our stay here was lovely. The place was clean and beautifully decorated. Situated on a canal with a hammock and outdoor table set, it’s the perfect environment for a weekend stay. It was clean and beautifully decorated and the bed and pull out beds were both comfortable. It was conveniently located at the south end of key largo, making it easy to get to islamorada. I’d highly recommend staying here and really enjoyed my visit.
Guest favorite
Home in Marathon
4.92 out of 5 average rating, 49 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

MaxsenaRating, 5 stars3 days ago
Super nice place to stay. Very comfortable.
Top guest favorite
A spacious waterfront deck features a thatched-roof structure providing shade. Comfortable seating arrangements are positioned around the area, with panoramic views of the calm Atlantic Ocean and distant islands visible in the background.
Home in Cudjoe Key
5 out of 5 average rating, 23 reviews

Tiki Time in Cudjoe Key 136

CourtneyRating, 5 stars2 weeks ago
Highly recommend anyone to stay here! The house is clean, well stocked, cozy, and quiet. The view is absolutely amazing! Sitting on the porch was our favorite way to start the day. Everyone was very friendly too.
Guest favorite
A patio area features bright blue chairs arranged along the railing, offering a view of the sandy beach and calm ocean. Palm trees sway gently in the background, with a wooden dock extending into the water, providing a serene coastal atmosphere.
Home in Marathon
4.95 out of 5 average rating, 59 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

ErinRating, 5 stars4 weeks ago
I can’t say how much we enjoyed this place. So private and clean. Beautiful view. Everything we needed was there. Sad to leave but back to real life. Thank you Thank you!
Guest favorite
An aerial view displays a charming home situated on a canal, surrounded by lush greenery. A wooden dock extends along the water, complemented by native plants. The building features a sloped roof and wrap-around porch, offering a serene and inviting water access area.
Home in Marathon
4.96 out of 5 average rating, 69 reviews

Private 174ft Dock, Boat Launch, Sombrero Beach

ChrisRating, 5 stars1 month ago
We had a great stay here, beds were comfortable and bathrooms were clean. Kids loved fishing off the dock - although the boat ramp was unavailable, we were able to use the ramp at the marina down the block ($30 each drop). Hosts were easy to communicate with and very helpful when we had a question. Wed definitely stay here again next time in Marathon.
Guest favorite
Home in Marathon
4.91 out of 5 average rating, 32 reviews

Viamarhe House-Private beach, Kayak, yard games

LisaRating, 5 stars2 weeks ago
We had a great stay. Enjoyed family time. The only feedback is that we didn’t realize there would be so much natural debris by the water which isn’t anyone’s fault. We just didn’t know so we were not prepared with water shoes.
Guest favorite
A modern kitchen features a large island with four yellow bar stools. Natural light fills the space through sliding glass doors that lead to a deck overlooking the canal. Light beige curtains frame the windows, enhancing the open and airy ambiance.
Home in Key Colony Beach
5 out of 5 average rating, 6 reviews

Key Colony Beach Waterfront 321

JeanneRating, 5 stars9 months ago
Great place right in the heart of Key Colony. House had all we needed and more to make our 8 day stay comfortable. Great boat dock with plenty of room for 2 31 ft boats.

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