Cottage vacation rentals in Sunset Key

4.9 out of 5 average rating, 154 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!

4.93 out of 5 average rating, 129 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.

4.87 out of 5 average rating, 67 reviews

Turtle Cove 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. ** TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of

4.97 out of 5 average rating, 35 reviews

An outdoor kitchen area features a sleek stone countertop with stainless steel cabinetry, providing ample storage. A vibrant blue plate and paper towel roll are positioned nearby. The background includes palm trees and a glimpse of the neighborhood, suggesting a relaxed, coastal setting.

Cottage in Marathon

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

A serene swimming pool area is seen under a clear blue sky, framed by swaying palm trees. Lounge chairs are positioned around the pool, inviting relaxation. The distance features a larger pool area, providing a peaceful backdrop for leisure activities.

4.71 out of 5 average rating, 152 reviews

Calypso Cottage

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

4.9 out of 5 average rating, 29 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 nearby !

Cottage in Little Torch Key

A long wooden dock extends into clear blue water, flanked by palm trees and lush greenery. Two turquoise chairs are positioned at the dock’s end, providing an ideal spot for relaxation and enjoying scenic water views under a bright sky dotted with clouds.

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, 11 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.

A gathering area is set among palm trees with several wooden picnic tables arranged on a sandy surface. The serene water is visible in the background, creating a relaxing outdoor space for guests.

4.63 out of 5 average rating, 112 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.

A clean countertop is showcased with a coffee maker and a single-serve coffee machine. Below, black storage baskets are neatly arranged, adding organization to the space. Natural light filters in through nearby windows, brightening the inviting kitchen area.

Cozy, Perfect Conch Cottage! - VO315

Cozy, Perfect Conch Cottage! VO315 Welcome to our Conch Cottage, located in the beautiful Florida Keys! Everything you need for your perfect vacation you will find in the cozy walls of our charming keys cottage. This cozy 2/1 has a Queen bed in the master off the bathroom and a murphy bed in the guest is also a queen. Large window ac units provide comfort throughout the cottage and the unit also has a washer and dryer. See additional house rules.