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, 101 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

Top guest favorite

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, 169 reviews

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

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.

The living room features a light-colored couch and love seat, complemented by decorative pillows. A coffee table sits in the center, and a Smart TV is mounted on the wall. Natural light is provided by the sliding glass doors, leading to an outdoor space.

4.96 out of 5 average rating, 114 reviews

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.

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.

4.89 out of 5 average rating, 170 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!

4.96 out of 5 average rating, 141 reviews

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

A tranquil pool is set against a backdrop of palm trees and a vibrant sunset. The water reflects the hues of the sky, creating a calming scene. Loungers are positioned along the poolside, offering a inviting space to relax.

4.78 out of 5 average rating, 23 reviews

2Bd/1Ba Waterfront Retreat w/35’ Dock

Discover the FL Keys in this bright & beachy 2-queen bed, 1-bath waterfront modular home in Venture Out on Cudjoe Key. Enjoy your fresh catch in the full kitchen, laundry in-house, nice wide canal with 35’ dock for your boat just steps from your door. Indulge in unparalleled amenities & scenic beauty: oceanfront pool, hot tub, marina w/marine fuel, wash station, store; tennis, bball, pickle ball, & playground. $125 add’l resort fee paid direct to Venture Out at gate. Incl Bikes & kayaks for use.

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, 77 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

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, 177 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 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, 180 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!

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.

4.91 out of 5 average rating, 161 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.

A balcony overlooking the calm bay features a colorful mosaic table and black chairs. Palm trees provide shade, and boats can be seen tied to the dock. The serene water reflects the surrounding greenery, creating a peaceful outdoor space.

4.97 out of 5 average rating, 31 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.

4.5 out of 5 average rating, 4 reviews

Enjoy Tropical Experience in Beachfront Casita

Escape to laid-back island living at La Siesta Resort & Villas in Islamorada. Set on a private beachfront with tropical cottages, enjoy poolside cocktails at Sidecar, kayak and paddleboard rentals, and shared access to sister resorts via water taxi or shuttle. Ideal for families, couples, or groups seeking a serene Keys getaway.

Popular amenities for Key West cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a pool

4.63 out of 5 average rating, 16 reviews

Colony Calypso - A quaint 1 Bedroom Cottage

The living room features high vaulted ceilings and large windows allowing natural light to fill the space. A comfortable sofa and chairs are arranged around a glass coffee table. Artwork adorns the walls, and a small dining area is visible in the background.

4.8 out of 5 average rating, 10 reviews

Ann Street Cottage

4.82 out of 5 average rating, 22 reviews

Colony Poolside: A charming bungalow near Duval

A spiral staircase ascends to a loft area in a well-lit living room, featuring high ceilings and a skylight. Two sofas are arranged around a coffee table on a neutral rug, with a lamp providing soft illumination. Colorful artwork is displayed on the walls.

4.8 out of 5 average rating, 5 reviews

Pete's Cottages: Twin Cypress cottages steps from

A kidney-shaped pool glistens under a partly cloudy sky, surrounded by lush tropical greenery. The pool features built-in seating areas and is framed by a clean white border. Nearby, wooden decking provides space for lounging and enjoying the serene outdoor environment.

4.95 out of 5 average rating, 42 reviews

Pete's West Cottage steps from Duval

A kidney-shaped pool with a waterfall is surrounded by lush tropical plants and palm trees. The water features a bright blue hue, inviting relaxation, while a deck with lounge chairs and a wooden fence creates a private atmosphere.

4.86 out of 5 average rating, 28 reviews

Pete's East Cottage: Cypress east cottage steps

A cozy studio features a queen-size bed adorned with patterned bedding. Comfortable seating is provided by two armchairs near a window overlooking tropical foliage. Warm light is emitted by ceiling fixtures, and shelves display decorative items, contributing to the inviting decor.

4.81 out of 5 average rating, 37 reviews

Bali Hideaway: A studio cottage that's perfect

Cottage rentals with free parking

The room features two spacious beds with light linens neatly arranged. A bedside lamp and a decorative vase provide subtle accents. The ceiling showcases exposed wooden beams. A doorway leads to a connected area, while a small refrigerator is visible in the corner.

Private room in Marathon

4.39 out of 5 average rating, 180 reviews

Tropical Cottages - Room # 14

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, 13 reviews

Keys Waterfront Oasis • Tiki • Private Pool • Dock

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.

4.65 out of 5 average rating, 17 reviews

Waterfront 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.

4.73 out of 5 average rating, 11 reviews

Waterfront Keys Cottage w/ Sleeping Loft Sleeps 8

4.68 out of 5 average rating, 47 reviews

1 Bdrm Keys Cottage with Sleeping Loft Sleeps 7

A charming cottage exterior features light blue siding and is accented by vibrant pink Adirondack chairs. Lush greenery surrounds the entrance, and flowering plants add color to the setting. A clear blue sky and tropical palm trees complete the welcoming atmosphere.

4.59 out of 5 average rating, 150 reviews

Tropical Cottages - Cottage # 10

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.

4.8 out of 5 average rating, 88 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

The spacious cottage interior showcases two queen size beds with light bedding, set against soft blue walls. A ceiling fan adds to the airiness, while a small dining table with black chairs sits nearby. A kitchenette area is visible in the background.

4.45 out of 5 average rating, 234 reviews

Tropical Cottages - Cottage # 03

Cottage rentals with a hot tub

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, 110 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.

4.64 out of 5 average rating, 125 reviews

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

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.

4.89 out of 5 average rating, 46 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.

4 out of 5 average rating, 7 reviews

Cozy, Perfect Conch Cottage! - VO315

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.

4.8 out of 5 average rating, 70 reviews

NAUTILUS...ocean front cottage retreat ~

An aerial view captures the vibrant community of Venture Out Residential Condominium, showcasing homes along the canal. Boats are docked nearby, and palm trees surround the outdoor seating areas. The clear water reflects the buildings, creating a serene waterfront atmosphere.