Cottage vacation rentals in Big Pine Key

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Popular amenities for Big Pine Key cottage rentals

Cottage rentals with a hot tub

Superhost
An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.
Cottage in Cudjoe Key
4.87 out of 5 average rating, 67 reviews

Turtle Cove Views at Venture Out

CooganRating, 5 stars1 month ago
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.
A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.
Cottage in Cudjoe Key
4.81 out of 5 average rating, 95 reviews

OCEANIA... water front cottage retreat ~

RachelRating, 5 stars7 months ago
If we could rate this 6+ stars out of 5, we would! Manuel was super easy to reach, he provided simple and clear instructions, the guards at the gate were easy to work with and available for 24/7 entry and check in.. the location is unbeatable for a boat owner! You dock right at your back door, clean your fish at the back door OR at the marina, immediate access to the Atlantic.. perfection. The home itself is extremely clean & beautiful. The kitchen and bathrooms were all stocked with anything you’d need as well as even the laundry room! We truly felt at home but twice as relaxed! Thanks Manuel!!
An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.
Cottage in Cudjoe Key
4.9 out of 5 average rating, 152 reviews

ATLANTIS...Ocean Front Cottage Retreat!

JeanRating, 5 stars1 month ago
Manuel's home was clean, bright, quiet, and peaceful with a million dollar view. It sits directly on big open water which we enjoyed from the nice open porch. We ate meals on the porch while relaxing and savoring the amazing view of the blue water and the two islands beyond. We never tired of the view. The whole neighborhood is quiet and clean, and there is a small beach and a pool. The check in/check out process was simple and Manuel was responsive with all communications. We enjoyed exploring Key West (about a 30-35 minute drive) and walking the old train/then road Old Seven Mile Bridge from Marathon Key to Pigeon Key. The Bridge is a beautiful 4 mile round trip walk to small Pigeon Key where we swam and participated in a guided walking tour and shark feeding. If you're looking for a peaceful, relaxing, home with an amazing view to get away from it all, Manuel's home is the answer! It was perfect for my husband and me.
Superhost
The two-story cottage is framed by lush tropical vegetation, with prominent palm leaves. Illuminated doorways reveal a welcoming interior, while a balcony overlooks the entrance, suggesting a space for relaxation. The exterior features light-colored walls that harmonize with the natural surroundings.
Cottage in Key West
4.75 out of 5 average rating, 32 reviews

Darling of Duval at Old Town

JoeRating, 5 stars1 month ago
What a great place to stay for a Key West trip! Perfect location, lots to do, super short walk to Duval St. Very easy check in, and Last Key were easily available for questions.
An aerial view presents a light blue cottage alongside a canal, with white lounge chairs positioned on the deck. A kayak rests in the water, surrounded by lush palm trees and calm, clear waters reflecting a bright blue sky.
Cottage in Cudjoe Key
4.88 out of 5 average rating, 59 reviews

NAUTILUS...ocean front cottage retreat ~

JessicaRating, 5 stars4 weeks ago
Super responsive host! Place was great if you’re looking for a relaxed vibe. Close enough to key west but much less crowded relaxing vacation. My kids loved the pool and ocean being so close.
A bright living area features a comfortable gray sofa and an upholstered ottoman. Large sliding doors open to a water view, letting in natural light. A small dining table with patterned chairs is positioned near the window, complemented by a ceiling fan and modern decor.
Cottage in Key Colony Beach
4.6 out of 5 average rating, 10 reviews

2BR dog-friendly water view stay, resort amenities

StephanieRating, 5 stars5 months ago
Perfect location for boaters and fishermen. Clean and mostly quiet canal with minimal low wake zone. House had all basics and very comfortable for my husband and I. Loved having the park nearby to take our dog, would recommend!

Pet-friendly cottage rentals

Superhost
The living area features a gray sofa complemented by a colorful area rug. A flat-screen television is mounted on the wall. A small bar with seating connects to the kitchen area, adorned with bamboo window treatments, enhancing the bright and airy ambiance.
Cottage in Key West
4.79 out of 5 average rating, 19 reviews

Colony Sunset- Bright and airy cottage

MaureenRating, 5 stars12 months ago
What a great find! Everything we needed was there! Quick walk to everywhere: beach, Duval street fun, restaurants and grocery store. So glad we went with this air bnb and not the hotel we normally go to. Saved so much money. Loved the privacy!
Guest favorite
Cottage in Islamorada
4.96 out of 5 average rating, 28 reviews

Floating 2 BD, 1 BATH Private Villa Pirates Lair

PaulRating, 5 stars2 weeks ago
The place was awesome! So perfect! They helped with getting our jetskis in the water and let us tie them up to the doc. We'll definitely be back. Thank you Toni and Jay!
A bright living area features exposed wooden beams and large windows offering views of the marina. Comfortable seating includes a dark sofa and wooden coffee table, complemented by a decorative rug. A wall-mounted television and a small dining space are also present.
Cottage in Islamorada
4.75 out of 5 average rating, 175 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

JaceyRating, 5 stars3 months ago
We loved staying here for the two nights we were on the Keys. The patio outside was great for looking at the stars or sipping coffee and watching manatees. We would definitely return!
Superhost
An open studio layout features high ceilings and light blue walls. A queen bed is positioned near the window, with a comfortable couch and a coffee table in the seating area. French doors lead to an outdoor deck, enhancing natural light in the room.
Cottage in Key West
4.67 out of 5 average rating, 30 reviews

Osprey @ Colony

FrancesRating, 5 stars1 month ago
Perfect place for two. Awesome location, within walking distance of Duval but far enough away that it’s nice and quiet at night. Beautiful little pool. Will 100% stay here again next visit to Key West
The overhead loft area features a cozy sleeping space with soft pillows arranged on a spacious bed. Natural light enters through multiple windows, illuminating the area. A wooden safety railing provides a safe transition to the open space below, which contains additional sleeping arrangements.
Cottage in Marathon
4.67 out of 5 average rating, 33 reviews

Cute 1B/1B Lofted Cottage

AmyRating, 5 stars3 weeks ago
What a beautiful, peaceful spot to stay! Family friendly and exceeded expectations. Great location to explore all of the Keys but always a nice, private and quiet place to come back to. Would absolutely stay here again!
Cottage in Marathon
4.75 out of 5 average rating, 12 reviews

Waterview 1B/1B Tiny Home

RuthRating, 5 stars3 weeks ago
We absolutely loved it here and would've happily stayed for weeks! The tiny house was cute, clean and comfy with everything we needed. The location was perfect, would give it 110%. Beautiful sea view, amazing sunsets and the children enjoyed the games in the clubhouse and the pool. There are also lots of things to do nearby. Probably the best place we've ever stayed.
A relaxing outdoor area features tall palm trees swaying gently in the breeze. A colorful hammock is strung between two trees, inviting rest. The walkway leads to a building with a casual vibe, surrounded by lush greenery under a clear blue sky.
Cottage in Islamorada
4.82 out of 5 average rating, 155 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

T LRating, 5 stars2 months ago
Toni was very nice. She went out of her way to make sure we were satisfied with everything. The bed was comfortable and we got a great night's sleep there on the water. Watching the fish jump and pelicans dive as we sat on the front deck was very relaxing.
A charming cottage exterior features light blue siding and is accented by vibrant pink Adirondack chairs. Lush greenery surrounds the entrance, and flowering plants add color to the setting. A clear blue sky and tropical palm trees complete the welcoming atmosphere.
Cottage in Marathon
4.62 out of 5 average rating, 116 reviews

Tropical Cottages - Cottage # 10

LoriRating, 5 stars1 month ago
The Airbnb had a great location. My husband enjoyed the local fishing, which was a block away. The Airbnb was clean and very comfortable. We also enjoyed the taco truck and Tiki bar located on the premises. The most important thing was that we could bring our dog Chloe and felt comfortable and safe. We will come back again to the cottage.

Private cottage rentals

Superhost
Cottage in Key West
4.77 out of 5 average rating, 13 reviews

Colony Calypso - A quaint 1 Bedroom Cottage

SalarRating, 5 stars8 months ago
Our stay was fantastic, the host was amazing and incredibly responsive. No issues at all, however, the Vacasa utility workers have a habit of entering the back patio areas unannounced. I think just a simple initial knock at the door, and a subsequent announcement of their entry would be satisfactory. This takes nothing away from the property or the hosts themselves, I believe Vacasa is a vendor. The stay itself was absolutely amazing, think rainforest escape to a beautiful place. The vibe was immaculate and I loved the pool. Stay here if you can, it is so worth it.
A concrete dock extends into the water, lined with teal chairs for seating. Nearby, a cleaning station appears on the left, while various boats are visible at the marina. Lush palm trees and a blue building provide a scenic backdrop under a partly cloudy sky.
Cottage in Marathon
4.67 out of 5 average rating, 6 reviews

Waterfront 1B/1B Tiny Home

MatthewRating, 5 stars1 month ago
We had a great stay in their tiny house. The neighbor’s were all nice and friendly. The locals that live inside the campground are absolutely wonderful very nice and full of local information where to go and what to do.
A communal heated swimming pool is surrounded by lush greenery and palm trees. Comfortable lounge chairs are positioned along the poolside, complemented by two blue umbrellas providing shade. A serene atmosphere is created by the clear blue skies above and the vibrant landscaping surrounding the area.
Cottage in Islamorada
4.78 out of 5 average rating, 79 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

JustinRating, 5 stars3 weeks ago
The place and location were perfect. We were looking for a no frills type of place so my kids would have to spend time without devices and just be outside. This little place is exactly what we needed, it’s just big enough to sleep, eat a quick breakfast and head out for the day on the keys. The pool area is really nice and everything was great. It does not come with any extras..like beach bike, beach chairs or extra beach towels so you may want to bring your own. We left a few behind for the next family to enjoy. Over all this was a very clean and nice place to stay in a good neighborhood located to almost everything.
Superhost
A charming entrance features double French doors framed by lush greenery. The brick pathway leads to the entrance, with soft lighting from wall sconces accentuating the space. Latticework indicates nearby outdoor areas, while bike racks complete the inviting entry.
Cottage in Key West
4.71 out of 5 average rating, 14 reviews

Colony Poolside: A charming bungalow near Duval

EricaRating, 5 stars17 months ago
We loved our time at Colony Poolside! We spent a long weekend at Colony Poolside (it was our second stay in this location). The rental was exactly like the pictures, clean and comfortable. The kitchen was well stocked, and there were even beach towels, sunblock and a workout mat. The pool was clean and quiet. Short walk to Duval and lots of great restaurants. We would highly recommend!
Superhost
A spacious living room features polished wooden floors and a striking spiral staircase leading to a loft area. A modern black sofa is paired with a sleek coffee table, while natural light streams in from a nearby window, highlighting a colorful artwork hung on the wall.
Cottage in Key West
4.82 out of 5 average rating, 22 reviews

Pete's East Cottage: Cypress east cottage steps

SaraRating, 5 stars1 month ago
Great location! Pool was great! We enjoyed our stay!
A tiki patio is visible with a thatched roof, surrounded by tropical palm trees. The setting features a private pool, inviting outdoor seating, and a hammock. Bright sunlight highlights the serene atmosphere, with views toward the home through sliding glass doors.
Cottage in Key Colony Beach
5 out of 5 average rating, 10 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

DawnRating, 5 stars12 months ago
Leeann’s place exceeded our expectations! She was incredibly responsive to any concerns or inquiries we had throughout our stay. The added perk of access to Glunz Beach Resort with its beach, pool, and gym made our experience even more delightful. The house was equipped with everything we needed for a comfortable stay. Thank you, Leeann!

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