Cottage vacation rentals in Big Pine Key

4.96 out of 5 average rating, 79 reviews

An aerial view of the property showcases a spacious swimming pool surrounded by lounge chairs. Lush greenery frames the area, enhancing the private setting. A nearby cottage is visible, along with a shaded patio area for outdoor relaxation.

Cottage in Islamorada

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

An aerial view showcases a resort-style pool area surrounded by palm trees, with sun loungers arranged around the pool's edge. The clear blue water contrasts with the sandy shore and the green of the adjacent canal, creating a relaxed atmosphere.

4.7 out of 5 average rating, 145 reviews

Calypso Cottage

This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your door, you will be able to enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, pickle ball, board games, wifi & roku) and of the community (Pools, spa, boat launch, sports courts, even a library and a general store!). You can use this magical location to launch all your Florida keys adventures! Canal patio for drinks? Lush screen porch for coffee? It's on!

Top guest favorite

Two bright blue Adirondack chairs and a small table are positioned on a wooden dock overlooking calm water. Lush greenery frames the scene, while a clear blue sky enhances the tranquil atmosphere. The dock offers direct access to the water, inviting relaxation.

Cottage in Islamorada

4.95 out of 5 average rating, 39 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage with Dockage. Short walk to world famous Lorelei for sunset celebrations. Great location for kayaking & paddleboarding. Custom length of stays can be arranged if booking a sandbar/fishing charter with our family. The fishing cottage built in the 1940s is not fancy, as photos show, but in the heart of Islamorada! Dockage available for additional $25 per night fee not included in nightly rate. Free trailer storage on site. Pet friendly :) 1 pet under 20 lb $150 fee.

A sunlit living space features large windows with scenic water views. A comfortable chair is positioned nearby a wooden media console with a TV. Tile flooring adds a clean, spacious feel to the room, complemented by light-colored walls and decorative starfish accents.

4.93 out of 5 average rating, 121 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Top guest favorite

An outdoor deck is visible along the canal, featuring a picnic table and two sun loungers. A kayak in bright orange and white rests on the surface. The sky is clear, with a few clouds, and a calm waterway is seen in the background.

Cottage in Marathon

4.97 out of 5 average rating, 32 reviews

Catch n' Relax Canalfront Cottage in Marathon

Enjoy our cottage right on a deep canal with 50' dock. Step right into your boat to fish the Atlantic Ocean & Gulf or just relax & enjoy the view! Enjoy an outdoor kitchen space for fish fry & Happy Hour drinks. Tan on our loungers or enjoy dinner under the stars. Kayaks/Bikes for you too. A Perfect location Minutes from Airport, 7Mile Bridge, Sombrero Beach & other Attractions. Close to shops & restaurants. Easily launch your boat from a free public marina nearby. Rental License #VACA-22-85

4.8 out of 5 average rating, 5 reviews

A welcoming entrance features natural cypress siding and wood accents. A small porch is visible, with a bench situated to one side. Light filters through the slatted shutters, creating a serene atmosphere. Nearby, tropical greenery adds a touch of nature to the setting.

Cottage in Key West

Pete's Cottages: Twin Cypress cottages steps from

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room has a spiral staircase to the loft second bedroom with unique glass railing. Large windows in the kitchen bi-fold away to allow serving directly to the pool

A waterfront patio features several blue lounge chairs adorned with red cushions, positioned along a concrete deck. Lush greenery and calm waters are visible in the background, providing a serene setting. Dock posts and a fish cleaning table are included along the edge.

4.86 out of 5 average rating, 36 reviews

Tidewater Views at Venture Out

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** TIDEWATER VIEWS is a cozy 800 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out Resort: a heated 80-foot pool with large Jacuzzi and Kiddie Pool,

An aerial view captures the vibrant community of Venture Out Residential Condominium, showcasing homes along the canal. Boats are docked nearby, and palm trees surround the outdoor seating areas. The clear water reflects the buildings, creating a serene waterfront atmosphere.

4.89 out of 5 average rating, 28 reviews

Conch Cabana in Paradise 23 miles outside Key West

Sparkling clean and bright 2Bd/2Ba vacation home in Venture Out Resort! Is located on a 60' wide canal, our Dock is 35’. With fish clean table, cleats, bumpers, shower and patio table with 4 chairs. 1 porch front yard and 1 Deck over looking the water. Just a few steps from the pool, hot tub , please be aware that they can close the pool and hot tub for emergency/ regular maintenance without any notice. VO Resort has a marina w/fuel, store, rec hall, tennis court. Great Restaurant near !

Cottage in Little Torch Key

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

4.96 out of 5 average rating, 110 reviews

A serene pool area is surrounded by lush tropical plants and swaying palm trees under a clear blue sky. A large blue umbrella provides shade over a lounging area, enhancing the inviting atmosphere of the outdoor space.

Cottage in Islamorada

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

A serene waterfront scene features calm turquoise waters with gentle waves. A thatched-roof gazebo extends over the water's edge, providing a shaded area. In the background, a row of palm trees sways slightly under the bright blue sky, adding to the tranquil atmosphere.

4.64 out of 5 average rating, 111 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

This mid-rise home is fully furnished with high ceilings throughout! The living room offers a flat screen television with sleeper sofa. Master bedroom features a queen bed with full bathroom and flat screen television. Guest bedroom features a full size bed and half bath. Additional amenities include large open porch with table and chairs, gas grill and central air conditioning and heat. Free WiFi offered in unit and in Community Recreation Center.