Cottage vacation rentals in Key West

A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.

4.97 out of 5 average rating, 91 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

An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

4.9 out of 5 average rating, 159 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!

The exterior of the cottage features a vibrant mural adorned with large floral designs, complemented by a light blue roof and shutters. Surrounded by lush greenery, the property sits on a textured gravel area under a clear blue sky.

4.96 out of 5 average rating, 49 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.

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

4.94 out of 5 average rating, 139 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.

5 out of 5 average rating, 5 reviews

Key West Cottage Du Soleil w/ Pool!

This two-bedroom Key West Writer's Cottage is a serene haven for creative minds and vacationers. It features a cozy living area with charming decor that inspires relaxation. Enjoy the relaxing deck for morning coffee or unwinding with a book, and take a refreshing dip in the inviting pool. Each comfortably furnished bedroom ensures a restful night’s sleep, and the fully equipped kitchen is perfect for cooking. Plus, you can easily bike to the nearby boardwalk and beach for fun in the sun!

A cozy living area features a brown leather sofa and a low wooden coffee table, set against a backdrop of wooden paneling. Large glass doors reveal a scenic view outside. A television is mounted on the wall, and decorative items are arranged on a nearby shelf.

4.77 out of 5 average rating, 159 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

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. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Cottage in Little Torch Key

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.

4.88 out of 5 average rating, 171 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

The private saltwater pool is framed by tropical plants and bright blue sky. Lounge chairs are positioned nearby, alongside decorative elements and pots. The serene atmosphere offers a refreshing retreat, inviting relaxation and enjoyment in the beautiful surroundings.

5 out of 5 average rating, 12 reviews

Luxurious Oasis on: 2BR w/Private Pool, Tiki, Dock

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, 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 serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.

4.97 out of 5 average rating, 122 reviews

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 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.

4.92 out of 5 average rating, 142 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.

The two-story cottage is framed by lush tropical vegetation, with prominent palm leaves. Illuminated doorways reveal a welcoming interior, while a balcony overlooks the entrance, suggesting a space for relaxation. The exterior features light-colored walls that harmonize with the natural surroundings.

4.75 out of 5 average rating, 36 reviews

Darling of Duval at Old Town

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. ** DARLING OF DUVAL and Last Key Realty's Five-Star In-Home Guest Services are the perfect combination to create the five star hospitality typically associated with luxury hotels - all in the Old Town location of your dreams.

A sailboat is moored near a wooden dock, surrounded by palm trees. The orange glow of sunset is visible in the background, reflecting on the calm water. The scene captures a tranquil moment along the bay.

4.96 out of 5 average rating, 26 reviews

Waterfront cottage w/ MotherInLaw suite&boat slip

The property is on the Bay, with a balcony in the palm trees and a large back porch on the water. Includes a ComPac sailboat, use of kayaks, bicycles and BBQ grill. Boat slip included! Located at Mile Marker 63, on Conch Key, the location is convenient to all Keys attractions: Key West, MM zero, State Parks, Museums, shopping, snorkeling and diving, and some of the best fishing in the world.

Popular amenities for Key West cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.

4.87 out of 5 average rating, 70 reviews

Turtle Cove Views at Venture Out

An outdoor seating area features a round table surrounded by iron chairs, overlooking tranquil waters. Lounge chairs are positioned along the railing. The covered porch provides shade, with lush greenery visible across the waterway, enhancing the serene setting.

4.88 out of 5 average rating, 40 reviews

Tidewater Views at Venture Out

The exterior of the Conch Cottage features a light green facade with large windows allowing natural light. Palm trees frame the entrance, and a clear driveway leads to the door marked with the number 315. A window air conditioning unit is also visible.

Cozy, Perfect Conch Cottage! - VO315

A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.

4.81 out of 5 average rating, 102 reviews

OCEANIA... water front cottage retreat ~

The exterior of a mid-rise home is shown, featuring a light-colored facade and a set of stairs leading to an elevated porch. The porch area is equipped with a table and umbrella, surrounded by tropical landscaping and a gravel driveway.

4.63 out of 5 average rating, 120 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.

4.72 out of 5 average rating, 159 reviews

Calypso Cottage

An aerial view presents a light blue cottage alongside a canal, with white lounge chairs positioned on the deck. A kayak rests in the water, surrounded by lush palm trees and calm, clear waters reflecting a bright blue sky.

4.79 out of 5 average rating, 66 reviews

NAUTILUS...ocean front cottage retreat ~

A bright living area features a comfortable gray sofa and an upholstered ottoman. Large sliding doors open to a water view, letting in natural light. A small dining table with patterned chairs is positioned near the window, complemented by a ceiling fan and modern decor.

Cottage in Key Colony Beach

4.55 out of 5 average rating, 11 reviews

2BR dog-friendly water view stay, resort amenities

Pet-friendly cottage rentals

A charming outdoor space is shown with a small circular table and two chairs set on a stone patio. Lush greenery surrounds the area, and wooden steps lead to the entrance of the cottage. A tree provides shade, enhancing the serene ambiance.

4.84 out of 5 average rating, 88 reviews

Hidden Oasis @ the Colony ~ Great location

A cozy living area features a gray sofa adorned with pirate-themed cushions, complemented by a decorative throw. Two large windows framed by red curtains allow natural light to brighten the space. A round rug with a compass design anchors the room, accompanied by a side table and lamp.

4.74 out of 5 average rating, 35 reviews

Floating 2 BD, 1 BATH Private Villa Pirates Lair

An open living area features warm wooden beams on the ceiling and large windows allowing ample natural light. A rustic coffee table is centered on a patterned rug, with a comfortable sofa positioned nearby. Barstools line a counter, creating a casual dining space.

4.76 out of 5 average rating, 176 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

An open studio layout features high ceilings and light blue walls. A queen bed is positioned near the window, with a comfortable couch and a coffee table in the seating area. French doors lead to an outdoor deck, enhancing natural light in the room.

4.67 out of 5 average rating, 33 reviews

Osprey @ Colony

A covered outdoor seating area features a round glass table and two chairs overlooking the blue ocean, framed by vibrant green palm trees. The tranquil beachfront path can be seen in the distance, promoting an inviting atmosphere for relaxation.

4.62 out of 5 average rating, 13 reviews

Waterview Keys Cottage w/ Sleeping Loft| Sleeps 7

An outdoor seating area is highlighted by a round wooden table surrounded by Adirondack chairs. A ceiling fan adds comfort, and the scene features expansive views of the water, with a dock visible in the background under a clear blue sky.

4.71 out of 5 average rating, 7 reviews

Waterfront Keys Cottage w/ Sleeping Loft| Sleeps 8

A charming exterior of a light blue house is shown against a clear sky. The house features large front windows, a decorative round window, and a small front porch with steps leading up. Outdoor seating in turquoise is visible nearby, set on a gravel driveway.

4.7 out of 5 average rating, 43 reviews

1 Bdrm Keys Cottage with Sleeping Loft| Sleeps 7

A charming outdoor patio area features a circular table with two chairs set on stone pavers surrounded by lush tropical plants. A canopy of palm trees provides shade, while the bright yellow exterior of the cottage is visible in the background.

4.94 out of 5 average rating, 16 reviews

NEW! - The Jolly Rooster Cottage - Walk to Duval

Private cottage rentals

Cottage in Little Torch Key

4.88 out of 5 average rating, 171 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

4.96 out of 5 average rating, 49 reviews

Waterfront Cottage Walk to World Famous Lorelei

A charming entrance features double French doors framed by lush greenery. The brick pathway leads to the entrance, with soft lighting from wall sconces accentuating the space. Latticework indicates nearby outdoor areas, while bike racks complete the inviting entry.

4.76 out of 5 average rating, 17 reviews

Colony Poolside: A charming bungalow near Duval

4.94 out of 5 average rating, 139 reviews

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

4.94 out of 5 average rating, 16 reviews

NEW! - The Jolly Rooster Cottage - Walk to Duval

5 out of 5 average rating, 5 reviews

Key West Cottage Du Soleil w/ Pool!

A living room features soothing blue and green tones, complemented by a vibrant green accent chair and decorative pillows. French doors open to the lush courtyard, allowing natural light to enhance the space, while a decorative rug and a glass coffee table provide a cozy gathering area.

4.87 out of 5 average rating, 52 reviews

Namaste: A blissful one bedroom cottage

A living area features a comfortable blue sofa paired with a matching armchair. A coffee table sits atop a decorative area rug. A modern television is positioned on a white entertainment unit. Natural light enters through a window with light-colored coverings, enhancing the spacious feel.