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

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, 99 reviews

OCEANIA... water front cottage retreat ~

DeniseRating, 5 stars1 month ago
Place was great. We loved the kayaks and Bikes that were there. Very clean and spacious. Beautiful view being on the canal. my negative I would say, which has nothing to do with the host, We were aware of the $125 resort fee, And our fee was increased to $145 cause my son’s large pickup. Curious as to what that fee actually pays for. We would definitely stay again.
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, 154 reviews

ATLANTIS...Ocean Front Cottage Retreat!

WendyRating, 5 stars1 month ago
We had an amazing 6-night stay at this waterfront Airbnb! The location is perfect—right on the water with gorgeous sunrise views. We used the provided kayaks every day, and my husband loved fishing off the deck while I relaxed in the sun. The house is super cute, clean, and beachy. The bed was very comfortable, and the kitchen was well-stocked with basics like spices and oil, making it easy to cook most of our meals. We also appreciated the strong, hot shower and provided toiletries. Extras like beach towels, umbrellas, fishing gear, and a washer/dryer made our stay even better. The area is peaceful, clean, and friendly—plus, Key West is just a short drive away. We’d definitely stay here again!
Superhost
An outdoor seating area features a round table surrounded by iron chairs, overlooking tranquil waters. Lounge chairs are positioned along the railing. The covered porch provides shade, with lush greenery visible across the waterway, enhancing the serene setting.
Cottage in Cudjoe Key
4.86 out of 5 average rating, 37 reviews

Tidewater Views at Venture Out

KatieRating, 5 stars1 month ago
Great location, and a very practical and cute little house. The neighbor who resides on the ocean side was wonderful and inviting, which made the stay so much better. Well stocked kitchen. Lots of clean towels and name brand starter essentials. The down side, there was a bag of (assumed??) dirty bedding left by the door, which I contacted our concierge about when we arrived, and it went ignored until I brought it up at check out again. It worked out fine though, my kids brought their own blankets and used them instead. Everything else was great though!
The exterior of the Conch Cottage features a light green facade with large windows allowing natural light. Palm trees frame the entrance, and a clear driveway leads to the door marked with the number 315. A window air conditioning unit is also visible.
Cottage in Cudjoe Key

Cozy, Perfect Conch Cottage! - VO315

StephanieRating, 5 stars2 months ago
Loved our stay! Clean place, great location and the community at VO is so nice. Great place to stay. Clean and cozy spot. Had everything we needed. Would definitely stay here again!
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
4.85 out of 5 average rating, 61 reviews

NAUTILUS...ocean front cottage retreat ~

AngelaRating, 5 stars1 month ago
Manuel was so kind and responsive! This place was sooo cute and perfect to stay in! The community felt super safe with the constant security, and he had so many amenities for us such as kayaks, fishing poles, bikes, kitchen supplies, hair dryer, etc. We had a slight issue with the wifi and he accommodated us to an extra day! It was soo sweet of him to do that and it made our stay extra fun:) Overall, I recommend 100% for anyone to stay here! It’s awesome. The pool and hot tub are so nice as well!
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
4.55 out of 5 average rating, 11 reviews

2BR dog-friendly water view stay, resort amenities

StephanieRating, 5 stars6 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 exterior view features a charming cottage framed by lush greenery and tropical plants. French doors open onto a wooden deck, inviting guests into the living space. A stone pathway leads to the entrance, while seating is offered nearby under the natural shade of palm trees.
Cottage in Key West
4.8 out of 5 average rating, 20 reviews

Colony Sunset- Bright and airy cottage

PollyRating, 5 stars3 weeks ago
The location was great. We parked our car and walked to everything. The condo was very nice and we loved the pool!
Superhost
A charming outdoor space is shown with a small circular table and two chairs set on a stone patio. Lush greenery surrounds the area, and wooden steps lead to the entrance of the cottage. A tree provides shade, enhancing the serene ambiance.
Cottage in Key West
4.83 out of 5 average rating, 84 reviews

Hidden Oasis @ the Colony ~ Great location

EricRating, 5 stars1 week ago
Great place for 2 people for a week. Very peaceful and quiet. Parking was easy and there was a park within walking distance for pets which was great. The cottage was very clean and the grounds were well maintained. Would stay again.
Guest favorite
A cozy living area features a gray sofa adorned with pirate-themed cushions, complemented by a decorative throw. Two large windows framed by red curtains allow natural light to brighten the space. A round rug with a compass design anchors the room, accompanied by a side table and lamp.
Cottage in Islamorada
4.84 out of 5 average rating, 32 reviews

Floating 2 BD, 1 BATH Private Villa Pirates Lair

SondraRating, 5 stars1 month ago
We are definitely planning on coming back to stay. We only spent 2 nights here and I’m disappointed we booked another spot in the lower keys for the rest of our trip. The guys at the front desk were very friendly and helpful! We grabbed some local shrimp and bbq’d on the grill. Totally a comfortable, peaceful, and relaxing place to stay, but very close to everything
An open living area features warm wooden beams on the ceiling and large windows allowing ample natural light. A rustic coffee table is centered on a patterned rug, with a comfortable sofa positioned nearby. Barstools line a counter, creating a casual dining space.
Cottage in Islamorada
4.75 out of 5 average rating, 175 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

JaceyRating, 5 stars4 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!
An outdoor seating area is highlighted by a round wooden table surrounded by Adirondack chairs. A ceiling fan adds comfort, and the scene features expansive views of the water, with a dock visible in the background under a clear blue sky.
Cottage in Marathon
4.67 out of 5 average rating, 6 reviews

Waterfront 1B/1B Tiny Home

MatthewRating, 5 stars2 months 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.
Cottage in Marathon
4.62 out of 5 average rating, 13 reviews

Waterview 1B/1B Tiny Home

RuthRating, 5 stars2 months 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 charming exterior of a light blue house is shown against a clear sky. The house features large front windows, a decorative round window, and a small front porch with steps leading up. Outdoor seating in turquoise is visible nearby, set on a gravel driveway.
Cottage in Marathon
4.66 out of 5 average rating, 38 reviews

Cute 1B/1B Lofted Cottage

JenniferRating, 5 stars1 week ago
Great distance to everything in the Keys. We stayed for several days and was able to hit all the spots- snorkeling, Key West, national parks. Close to restaurants, fishing and much more. Manager and maintenance were very responsive to questions, within minutes. Would stay here again!
A cozy living area features a brown leather sofa and a low wooden coffee table, set against a backdrop of wooden paneling. Large glass doors reveal a scenic view outside. A television is mounted on the wall, and decorative items are arranged on a nearby shelf.
Cottage in Islamorada
4.79 out of 5 average rating, 156 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

T LRating, 5 stars4 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.

Private cottage rentals

Guest favorite
Cottage in Key West
4.73 out of 5 average rating, 15 reviews

Colony Calypso - A quaint 1 Bedroom Cottage

DianeRating, 5 stars1 month ago
Nice little space for 2. Spacious rooms, great location. Privacy, quiet street Easy to walk or bike to many restaurants, museums, shops Nice little pool, there are beach towels available to use We would definitely recommend and stay again if in the area b
Superhost
The entrance to the cottage is framed by tropical plants and trees, creating a lush and inviting atmosphere. A comfortable seating area with a small cushion is positioned to the side of the door, which features a glass panel and is surrounded by neutral-colored siding.
Cottage in Key West
4.78 out of 5 average rating, 9 reviews

Ann Street Cottage

PaigeRating, 5 stars2 months ago
Comfortable cottage for 2 adults. Cooked dinner in a few nights, breakfast as well. Clean rooms, kitchen, bathrooms & bedding. Took a day to figure out where laundry was, but once we did more snooping, we found it across the small deck area. Only complaint/attention to maintenance: the decking off the living rm/bedroom is rotted. Extremely soft and about to break thru walking across it. Someone's likely to get hurt if the boards give way. Also the patio table on the deck should be replaced with something a little sturdier. It's shaky and legs are wobbling on the table. Our stay was very comfy and enjoyable. Easy walk to activities/bars/restaurants, yet tucked away enough that it was mostly quiet & definitely private our entire stay.
A welcoming outdoor space features adirondack chairs arranged on a wooden deck. A small round table is positioned nearby, surrounded by lush tropical foliage. Sunlight filters through the greenery, creating a serene atmosphere for relaxation.
Cottage in Islamorada
4.78 out of 5 average rating, 82 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

DonnaRating, 5 stars2 weeks ago
Great choice! Very close to everything, central. Pool was so nice & our own mostly. Cottage is modern clean & comfortable. Perfect for a girls trip!
A winding brick pathway leads through lush greenery toward an outdoor picnic area featuring a thatched-roof structure. Dining tables and chairs are arranged under the canopy, surrounded by tropical plants and trees, creating a serene environment for gatherings.
Cottage in Marathon
4.42 out of 5 average rating, 219 reviews

Tropical Cottages - Cottage # 03

AndrewRating, 5 stars2 months ago
The cottage was cute, comfortable and made a great central location for all our excursions. Loved having a tiki bar and taco truck waiting for us after a long day. We loved our stay.
Superhost
A balcony overlooking the calm bay features a colorful mosaic table and black chairs. Palm trees provide shade, and boats can be seen tied to the dock. The serene water reflects the surrounding greenery, creating a peaceful outdoor space.
Cottage in Marathon
4.96 out of 5 average rating, 26 reviews

Waterfront cottage w/ MotherInLaw suite&boat slip

RachelRating, 5 stars10 months ago
We absolutely loved this charming cottage and Conch Key. Barry made sure we had everything we needed, and offered advice and insight into the surrounding area. The views from the dock and the character of the cottage made our trip everything we wanted it to be. We will definitely be back!
Superhost
A wall-mounted dispenser holds two bottles labeled 'Wave Sensation,' featuring a citrus and sea foam body wash and conditioning shampoo. The bottles rest against a tiled surface with warm tones, emphasizing a modern and practical bathroom design.
Cottage in Key West
4.83 out of 5 average rating, 23 reviews

Pete's East Cottage: Cypress east cottage steps

AmberRating, 5 stars1 month ago
We had a great stay. The pool was perfect in the heat of the afternoons, and so many great restaurants and sites to see within walking distance.
A garden view is captured through open French doors, revealing a serene outdoor space. Two patterned chairs flank a small table, surrounded by lush greenery and shaded by trees, creating an inviting spot for relaxation. The tiled floor extends into the outdoor area.
Cottage in Key Largo
4.25 out of 5 average rating, 4 reviews

Seaside Cottage White Beach 5 min paddle! Sleeps 4

DominiqueRating, 5 stars52 months ago
Wish we could’ve stayed here longer! You get an amazing view by the water, very central location. Joyce was an amazing host very quick to respond and helpful. Definitely would recommend for a nice quiet stay in the keys.
Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviews

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

MatthewRating, 5 stars2 months ago
What a fantastic place to stay in Marathon! LeeAnn really makes sure you feel right at home. Forgot a toothbrush? Didn't pack or want to buy shampoo? No problem, it's there! The pool is amazing, house is spotless, and the Key Colony Beach community is the best. It is quiet and relaxing while also being in the heart of everything to do in the Florida Keys. LeeAnn is so nice and responsive, she got back to us quickly with any questions that we had. Overall, this was one of the nicest places that my family and I have ever stayed on a vacation. 10/10 would recommend to anyone!

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