Townhome holiday rentals in Key West

A shared pool area is depicted, featuring clear blue water and a thatched roof gazebo. Surrounding palm trees and lush greenery create a serene atmosphere. Lounge chairs are placed along the pool deck, complemented by the light-colored brick pathway paving the area.

4.92 out of 5 average rating, 312 reviews

Comfortable, clean, beautiful home in Key West

Introducing a brand new property hosted by AirBnb Superhost Roy Svenningsen. This home was fully renovated in January 2019. It features all new furnishings, stainless steel appliances, new flooring, marble countertops, and top quality mattresses. I look forward to hosting you in this beautiful family oriented gated community situated across from the Key West Golf Course and only 3 miles from Duval St. The home comes with parking for 2 cars. I am always available to answer any questions. Roy

The modern kitchen features stainless steel appliances, including a refrigerator and oven. White cabinetry and a light countertop provide a bright atmosphere. A dining area is visible nearby, with seating for multiple guests. Large windows allow for natural light and views of the outdoor scenery.

4.81 out of 5 average rating, 177 reviews

Villa 5020 on Duck Key BOAT SLIP available

Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

A shaded outdoor dining area features a wooden table surrounded by chairs, with a view of the private canal lined with palm trees. Nearby boats are docked along the lush green banks, creating a serene waterfront setting.

4.96 out of 5 average rating, 158 reviews

Boater’s Paradise 3br/2.5ba at Coral Lagoon

*PLEASE NOTE* Villa slips/canal are under construction until March 2026. Please inquire before booking. Spectacular PET FRIENDLY 3 bed/2.5 bath 1350sf villa in beautiful Coral Lagoon, complete with a 40 foot wet slip and all the amenities! Spread out and enjoy the spacious, clean interior with free high speed wifi. Step outside to your boat and enjoy all the Gulf and Atlantic have to offer - both easily accessible in minutes. Relax with a drink at the pool after a long day of fun in the sun.

A spacious patio is visible, featuring a round wooden table surrounded by four chairs. The view includes calm waters framed by palm trees and lush greenery, under a sky dotted with fluffy white clouds.

4.82 out of 5 average rating, 163 reviews

The Ocean Beckons! 2/2 Village at Hawks Cay 5047

The Village at Hawks Cay Villa 5047 on Sunset Village Drive is located on Duck Key. Let this astonishing villa be your home away from home for your Next Florida Keys vacation. Captivating decor with the Florida Key in mind will keep you both comfortable and relaxed for your much needed vacation. Sip on your favorite cocktails from the patio overlooking the water or enjoy the water directly from your Villa or walk the waters edge with nature on Duck Key as your own back yard.

A tranquil outdoor pool is surrounded by palm trees, with lounge chairs and tables positioned for relaxation. Umbrellas provide shade near the water, while a charming cottage can be seen in the background under a clear blue sky.

4.86 out of 5 average rating, 226 reviews

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

A charming two-story villa exterior is shown, featuring a light blue and yellow color scheme. Steps lead to the entrance, framed by greenery and a white picket fence. A palm tree stands nearby, contributing to the tropical ambiance.

4.94 out of 5 average rating, 168 reviews

2B/2.5B Villa at Village at Hawks Cay with Spa

Our Villa is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high-end finishes, comfy beds and plenty to do in the surrounding areas, the Villa offers something for everyone. There is an in-ground splash pool located on the patio. It is not a hot tub but reaches a maximum temperature of 104 degrees for those desiring heat.

A private outdoor space is surrounded by lush greenery, featuring a small dipping pool with clear water. Comfortable lounge chairs are positioned beside the pool, and a dining table with chairs is set up on the wooden deck, ideal for enjoying meals in a serene environment.

4.96 out of 5 average rating, 113 reviews

Windsor Townhomes #3

Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has been created to meet your every need. The location is perfect; just three short blocks from Duval Street and tucked away on a quiet lane so you can choose your level of activity. The over 1700 square foot townhome is easily accessible to the action of Duval, and yet private and quiet for those wanting peace and tranquility.

A serene community pool is surrounded by lush tropical foliage and palm trees. Sun loungers are arranged along the edge, complemented by a shaded seating area nearby. The clear water reflects sunlight, creating a calming ambiance in the outdoor space.

4.96 out of 5 average rating, 45 reviews

Casa Coral

***Monthly Discount Promotion for August, September and October*** Bright and airy, Casa Coral offers an open living concept with all your vacation needs. This two bedroom, two and a half bath townhouse offers 3 outdoor balconies with seating and plenty of covered space to park your cars. Bikes and beach gear (no snorkel gear) provided. Please note: Bar-B-Q Grill pictured is now located in the carport below.

A stilt home is shown alongside a crystal clear canal, featuring a sand-colored patio with a tiki hut. Coastal greenery is visible, along with a white railing lining the water's edge. The building showcases multiple balconies and provides a sunlit atmosphere.

4.81 out of 5 average rating, 156 reviews

KCB Waterfront Split Home Walkable to Cabana Club

3BR/ 2 BA stilt home on crystal clear canal with open water views on deep water with 30 foot boat slip on a cul de sac. Short walking distance to multiple restaurants/bars, shops, and the Cabana Club with beach, pool, and hot tub. Fenced in waterfront patio with tiki hut. Kid friendly, with toys and high chair. Covered parking. Guests required to sign Regulations for Key Colony Beach form.

A bright and airy living area is filled with natural light from large windows offering expansive water views. A comfortable light blue sofa and a matching armchair provide seating. A decorative coffee table sits in the center, and tropical plants are visible outside.

5 out of 5 average rating, 16 reviews

Exceptional Water View With Boat Dock!

This is the best kept secret. 10 miles from Duval St. for the night life, but a total private oasis if you are looking for a true get away. This is an end unit with a water view from every window in a gated community with a salt water pool. Wake up to an ocean view and have cocktails on the patio. This is a brand unit that has recently been completely renovated.

An aerial view showcases the resort's layout, featuring a sparkling pool surrounded by palm trees and lounge chairs. A canal runs parallel to the property, with well-maintained pathways visible alongside the greenery and buildings.

4.9 out of 5 average rating, 152 reviews

Coral Lagoon* Winter specialrates*read description

* Starting the month of Aug we are offering discounted rates due to seawall construction (weekdays 8am-5pm) * Please inquire for further details* BOAT SLIP INCLUDED IN DISCOUNTED RATE* Coral Lagoon Resort~Anglers Paradise, canal front with 5 min access to ocean and gulf ~slip available/ included upon request-Villa 7-Pet friendly

A charming entrance to the villa is visible, framed by well-maintained greenery. White picket fencing and vibrant pink plants line the approach to a welcoming front door, which features a glass panel and an oval window. Subtle landscaping enhances the tropical feel.

4.82 out of 5 average rating, 148 reviews

Plunge Pool Villa on Blue Water Lagoon

7/18 NEW CENTRAL AIR INSTALLED LAST MINUTE DATES AVAILABLE AUGUST! YOUR TROPICAL PARADISE AWAITS. TWO BEDROOM 2 1/2 BATH SPA VILLA OVERLOOKING BLUE WATER LAGOON. SLEEPS 6 COMFORTABLY. GREAT FOR COUPLES, FAMILIES, HONEYMOONERS, FISHERMAN, GIRLS WEEKEND! 7 NIGHT MINIMUM IN HIGH SEASON. 3 NIGHT MINIMUM IN OFF SEASON.

Popular amenities for townhouse rentals in Key West

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly townhouse rentals

An aerial view presents the Coral Lagoon Resort, featuring white-roofed town homes surrounded by lush greenery. The marina showcases several boats docked in clear blue waters, with a boat ramp and a building in the background, completing the vibrant coastal scene.

4.8 out of 5 average rating, 51 reviews

Beautiful Coral Lagoon #12 in #1 Resort - Marathon

A private balcony is adorned with colorful outdoor furniture, including chairs and a table. Lush green grass extends towards the waterfront, framed by swaying palm trees. Scenic views of the calm water and horizon create a serene outdoor space.

4.76 out of 5 average rating, 38 reviews

Sea Le Vie - Indigo Reef 56 - 3BR with 31' Dockage

4.5 out of 5 average rating, 4 reviews

Waterfront Keys Home - Spectacular View, 37' Dock

4.93 out of 5 average rating, 262 reviews

Spotlessly clean 3 bedroom/3-bathroom family home

5 out of 5 average rating, 5 reviews

Oceanfront Boho Chic Townhouse

5 out of 5 average rating, 7 reviews

An aerial view showcases a serene pool area surrounded by lush palm trees, leading towards the vibrant blue-green waters of the Atlantic Ocean. White condominium buildings complement the tropical landscape, while fluffy clouds drift across the sky, adding a sense of tranquility to the scene.

Townhouse in Islamorada

Forever Views

A covered outdoor balcony is visible, featuring wooden deck chairs arranged for relaxation. The railing offers unobstructed views of the water and lush greenery beyond, complemented by a clear blue sky. Ceiling fans are positioned above for added comfort.

4.84 out of 5 average rating, 31 reviews

Tipsy Turtle - Amazing, Updated Villa On Duck Key!

Townhouse in Layton

4.88 out of 5 average rating, 16 reviews

Florida Keys Getaway w/ Stunning Ocean Views

Townhouse accommodation with a washing machine and dryer

The exterior of a two-story townhome is shown, featuring light blue siding and white staircases leading to the second floor. Lush greenery and colorful flowers line the walkways, providing a vibrant landscape.

4.79 out of 5 average rating, 73 reviews

KCB 2BR/2BA Townhome w/ Cabana Club's Beach & Pool

The duplex exterior features light blue siding and a raised structure supported by concrete pillars. Two sets of white stairs lead to the entrance, flanked by landscaped areas with shrubs and ground cover, creating a welcoming approach. The clear sky complements the inviting design.

4.88 out of 5 average rating, 88 reviews

KCB 2BR/2BA Duplex w/ Cabana Club's Beach & Pool

An outdoor patio area features a thatched-roof gazebo with bar stools arranged for comfortable seating. A private pool is visible beside lounge chairs, with lush greenery and palm trees providing a tropical backdrop. A grill is positioned nearby for outdoor cooking.

Steps away from Cabana Club, 4 bed 3 bath, kayaks

A private pool glistens under the bright sky, accompanied by lounge chairs and tropical landscaping. The canal is visible in the background, with a paddle board propped against the wall, enhancing the modern coastal ambiance of the outdoor space.

5 out of 5 average rating, 4 reviews

Cabana Club Privileges! Paddleboards, Bikes, Kayak

A spacious living area features a comfortable cream sofa and an accent chair, complemented by a light area rug. Natural light fills the room through large windows, and a dining area showcases a modern kitchen with wooden cabinetry and bar stools. Decorative artwork adds a calming touch.

4.97 out of 5 average rating, 39 reviews

Sombrero Reef Light Suite

A spacious living area is shown with hardwood flooring and a sectional couch. A round coffee table sits in front of the couch. The kitchen bar with stools is visible, and a bottle of champagne is placed on the countertop. Windows allow natural light to fill the room.

4.79 out of 5 average rating, 57 reviews

American Shoal Light Suite

A crystal-clear saltwater pool reflects the sunlight, surrounded by lush tropical landscaping. Several lounge chairs are positioned along the pool deck, while vibrant palm trees and greenery create a serene atmosphere in the backdrop.

4.87 out of 5 average rating, 201 reviews

*Sparkling new kitchen* 3 bedroom/3 bath home.

An open living area is showcased, featuring a spacious gray sofa and wooden accent chairs. A round coffee table sits in the center, with light streaming through the windows. The kitchen area features wooden cabinetry and modern appliances, complementing the overall neutral color palette.

4.87 out of 5 average rating, 71 reviews

Alligator Reef Light Suite

Townhouse rentals with a patio

A private patio area features a plunge pool surrounded by lush tropical landscaping. Two lounge chairs are positioned nearby, offering a relaxing space. A light blue sky with scattered clouds creates an inviting ambiance, while palm trees add a touch of the tropics.

5 out of 5 average rating, 88 reviews

Duck Key *Delight* private plunge pool

An aerial view showcases a waterfront villa surrounded by vibrant blue waters. Lush greenery lines the shoreline, while neighboring properties reflect a tropical aesthetic. A wooden dock extends into the canal, providing access to boats and scenic views of the surrounding area.

4.85 out of 5 average rating, 122 reviews

Waterfront Duck Key Villa - Sleeps 8 (7058)

The townhouse features a modern exterior with a metal blue roof and three levels of balconies. Each balcony is furnished with seating, overlooking the calm waters of the Yacht Harbor. Lush greenery surrounds the property, enhancing the coastal setting.

5 out of 5 average rating, 3 reviews

Bonefish Yacht Club

The spacious community pool is surrounded by tropical palm trees and features a thatched roof tiki area. Sun loungers are positioned along the pool deck, offering ample relaxation space. The clear blue water glistens under a bright sky, inviting guests for a refreshing swim.

4.96 out of 5 average rating, 24 reviews

Stunning Bonefish 3/3 Water Views & Pool

A serene outdoor space features two wooden lounge chairs positioned on a grassy area beside calm waters. A small table is placed nearby, and a private dock extends towards the water, flanked by lush greenery in the background under a bright blue sky.

5 out of 5 average rating, 8 reviews

Castillo Del Mar- Ocean access from your backyard

Aerial view reveals a row of charming villas and lush greenery along a waterfront. The serene water reflects the sky, with docks visible in the background. This peaceful setting showcases inviting coastal living in the Florida Keys.

4.83 out of 5 average rating, 71 reviews

2/2.5 Village at Hawks Cay - SPECTACULAR SUNSETS

An exterior view of a pet-friendly property surrounded by palm trees and greenery. The gravel area in front offers ample space for parking. Bright blue planters filled with foliage add a touch of color, while the clear sky provides a sunny backdrop.

4.88 out of 5 average rating, 17 reviews

7-Mile Bungalow

A shaded outdoor porch features four blue adirondack chairs arranged around a round table, overlooking tranquil water views. The surrounding area is adorned with lush greenery and distant views of a bridge, creating a serene space for relaxation.