Cottage vacation rentals in Key West

4.96 out of 5 average rating, 84 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

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, 41 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 $50 per night fee not included in nightly rate. Free trailer storage on site. Pet friendly :) 1 pet under 20 lb $150 fee.

A clear view of the waterfront features a well-maintained seawall alongside tranquil blue waters. Palm trees line the shore, offering a tropical feel. The space is enhanced by direct access for boating activities, emphasizing the serene and inviting coastal environment.

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

Top guest favorite

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

4.97 out of 5 average rating, 34 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

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!

Cottage in Little Torch Key

A wooden dock extends over tranquil waters, featuring two blue chairs positioned for scenic views. Sunlight reflects off the water's surface, while a clear blue sky and scattered clouds create a serene backdrop. The dock provides access to fishing and relaxation.

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, 113 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 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.

4.9 out of 5 average rating, 348 reviews

A vibrant waterfront scene features a thatched-roof structure with several palm trees surrounding it. Jet skis are docked alongside a wooden pathway. Colorful umbrellas offer shade to seating areas, creating a welcoming atmosphere for visitors enjoying the sunny Florida weather.

Cottage in Key Largo

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. Be sure to meet 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

4.91 out of 5 average rating, 130 reviews

Palm trees frame a sandy path leading to the beach. Gentle waves can be seen lapping at the shore under a partly cloudy sky. Lush grass grows on either side, adding a serene touch to the coastal scene.

Cottage in Key West

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.