Cottage vacation rentals in Key West

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Key West

Guests agree: these cottages are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Islamorada

4.96 out of 5 average rating, 56 reviews

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

Guest favorite

Cottage in Islamorada

4.96 out of 5 average rating, 25 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.

Guest favorite

Cottage in Cudjoe Key

4.92 out of 5 average rating, 99 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.

Guest favorite

Cottage in Marathon

4.96 out of 5 average rating, 24 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

Guest favorite

Cottage in Key Largo

4.97 out of 5 average rating, 65 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

ACTUAL LOCATION: within KeyLargoKampground.com Gated Community Lot #66 with BOAT DOCK for 25' OUTSIDE: ~ Large deck/ dock, Grill, Swim Ladder, tiki hut with swing and dining and Pub table. Parking for 1 truck & 1 car. ~ steps from the cottage Dock out back in 30' deep 100' wide Deep water swim canal with tropical fish along the banks, occasional Manatee, tarpon and finger mullet in cooler months. Maybe a porpoise. Kayack, board or Fish off dock. Walk to moon lit beaches in the park.

Superhost

Cottage in Cudjoe Key

4.86 out of 5 average rating, 35 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

Cottage in Islamorada

4.86 out of 5 average rating, 148 reviews

FLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Guest favorite

Cottage in Little Torch Key

4.9 out of 5 average rating, 155 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!

Guest favorite

Cottage in Key Largo

4.89 out of 5 average rating, 56 reviews

Kampground Paradise w/ Kayaks,Heated Pool & Marina

Enjoy the ocean just steps away from Life in Paradise! This hidden gem is located in the community of Key Largo Kampground. This home has all the amenities for you to escape to the keys and soak in all that the sun and sea have to offer. The community offers a marina, heated pool, playground, two small private beaches, volleyball and basketball courts, and more! It offers ample room for boat parking, RV's, and all the toys! This is the perfect keys hideaway!

Guest favorite

Cottage in Islamorada

4.98 out of 5 average rating, 90 reviews

2br/1ba w pool, 5 mins to beach and 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!

Guest favorite

Cottage in Key Largo

4.94 out of 5 average rating, 49 reviews

Spacious cottage - the Calusa campground-keylargo

Comfortable and spacious cottage in the center of KEY LARGO, close to all activities, Publix, bars and restaurants. ENJOY THE BEST SUNSETS OF THE FLORIDA KEYS IN THE HAMMOCK AREA. The facility park has a heated pool, basketball court, tennis court, boat ramp, marina and a children’s playground. Calusa is conveniently located next to John Pennekamp Park, Fishing Charters, Snorkeling, Scuba Diving and some of the best Seafood restaurants in town.

Guest favorite

Cottage in Key Largo

4.89 out of 5 average rating, 300 reviews

Cottage By The Sea

Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Behind the Cottage is Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals