Cottage holiday rentals in Sunset Key

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

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

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!

Osprey @ Colony

Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Perfectly located at the Colony on Olivia Street, just two blocks from famous Duval Street, this ground-floor studio suite is equipped to make your stay in the islands comfortable and convenient. Osprey is both removed from and integrated into Old Town Key West. It is tucked away in a quiet neighborhood, but close enough to walk to any bar, restaurant, shop, or gallery. This is a non-smoking unit designed to accommodate two

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!

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,

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 !

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!

NEW! - The Jolly Rooster Cottage - Walk to Duval

We’re thrilled to welcome you to our newly renovated, standalone cottage. Nestled just one block from vibrant Duval Street, you’ll be steps from Key West’s best dining, shopping, and nightlife Thoughtfully designed for relaxation and comfort, the Jolly Rooster comfortably hosts up to six guests and blends island charm with modern convenience. Our cottage comes fully equipped for a memorable stay. Come unwind, explore, and experience the best of island living at the Jolly Rooster!

Bali Hideaway: A studio cottage that's perfect

Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath as well as a plethora of delicious restaurants. Venture just a short distance further to Mallory Square or the famous Historic Seaport.

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.

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.