Cottage vacation rentals in Sunset Key

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Top-rated cottage rentals in Sunset Key

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Superhost

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.

Cottage in Cudjoe Key

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!

A dining area is presented with a large white table surrounded by matching chairs. A shell chandelier hangs above, and light turquoise walls complement the ocean views visible through large windows. Turtle decorations add a coastal touch, enhancing the serene environment.

Cottage in Cudjoe Key

4.9 out of 5 average rating, 152 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

Guest favorite

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.

Cottage in Cudjoe Key

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

Superhost

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

4.8 out of 5 average rating, 5 reviews

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

Superhost

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.

Cottage in Cudjoe Key

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,

Guest favorite

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.

Cottage in Cudjoe Key

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 !

Guest favorite

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.

Cottage in Little Torch Key

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!

Cottage in Key Colony Beach

5 out of 5 average rating, 10 reviews

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

Lilo's in The Keys, a tropical paradise! This cherished waterfront gem has been a beloved destination for years. The perfect getaway to unwind and indulge in the island lifestyle. Nestled among tropical landscaping, Lilo’s boasts a private saltwater pool, a tiki patio for outdoor lounging and a dock for your boat. Your stay includes kayaks and bicycles, so you can explore the beauty of Key Colony Beach at your own pace. The home is fully equipped with all the comforts of home.

Superhost

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.

Cottage in Cudjoe Key

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.

Superhost

A charming yellow cottage is framed by a white picket fence, with blue awnings above the windows and door. The entrance is marked by a simple white door. Lush greenery surrounds the property, enhancing the inviting appearance of the home.

Cottage in Key West

4.91 out of 5 average rating, 124 reviews

The Dancing Rooster - 1 Block to Duval!

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.