Townhome holiday rentals in Key West

5 out of 5 average rating, 17 reviews

Discount - Jan 31! 3 Bed/3 BA Cabana Club Access!

Sun Kissed Tails in Hawks Cay on Duck Key is a 3 bedroom 3 bath townhome with a fully stocked kitchen in the Hawks Cay resort on Duck Key, MM61. This property does not have a boat slip, but you can possibly rent one based on availability. Enjoy the local beaches a short drive away (Coco Plum Beach and Sombrero Beach) and ENJOY THE POOL AND BEACH AT THE OCEAN FRONT CABANA CLUB, just a 15 drive to Key Colony Beach. The Cabana Club has an olympic size pool, Tiki Bar and restaurant, ocean front sand

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, 159 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 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.

Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and two queen beds. The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer installed. The salt water pool is perfect for lazing away your days. There is on street parking for two cars. The center of town is ten minutes away. An entire home for the price of one hotel room.

The charming cottage displays a pastel-colored exterior with a triangular roof and white trim. A small front porch is set above the entrance, flanked by two sets of French doors. Lush greenery and a white picket fence enhance the welcoming entryway.

4.96 out of 5 average rating, 186 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage 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 Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

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, 230 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 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, 114 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, 157 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.

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

Townhouse in KEY COL BCH

Blue Marlin:Waterfront 2b/2b,Cabana Club, Ocean Sd

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 view unfolds from a porch, showcasing a lush green lawn leading to a canal with boat slips. Palm trees sway gently in the breeze under a partly cloudy sky, while sunlight reflects on the water, enhancing the tranquil setting.

4.72 out of 5 average rating, 18 reviews

Fish & Fun - 3BR Indigo Reef #9 with 31' Boat Slip

5 out of 5 average rating, 5 reviews

Oceanfront Boho Chic Townhouse

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

5 out of 5 average rating, 7 reviews

Forever Views

Townhouse in Layton

4.88 out of 5 average rating, 16 reviews

Florida Keys Getaway w/ Stunning Ocean Views

A tranquil view showcases calm turquoise waters framed by lush greenery. The image captures the gentle contours of manicured bushes and trees, creating a serene atmosphere. The distant trees line the water's edge, contributing to the natural beauty of the scenic landscape.

4.7 out of 5 average rating, 316 reviews

Sunset Views!

A bright and airy living area features a comfortable sofa and armchair, with large glass doors offering access to a private patio. A ceiling fan hangs above, and a TV sits on a light-colored entertainment unit, enhancing the space's open feel.

4.81 out of 5 average rating, 68 reviews

Beachy Townhome Perfect For A Relaxing Getaway!

Townhouse accommodation with a washing machine and dryer

Top guest favourite

A canal-front home is showcased with a scenic view, featuring a grassy area leading to the water. The exterior includes a spacious deck and large windows, inviting natural light. Surrounding palm trees and the evening sky enhance the tranquil coastal setting.

4.93 out of 5 average rating, 30 reviews

Bayside Paradise - B

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

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, 314 reviews

Comfortable, clean, beautiful home in Key West

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

4.93 out of 5 average rating, 262 reviews

Spotlessly clean 3 bedroom/3-bathroom family home

A private pool is situated adjacent to the ocean, surrounded by lounge chairs and palm trees. The clear turquoise waters of the ocean are visible in the background, with a boat dock and a blue sky dotted with fluffy clouds above.

4.4 out of 5 average rating, 20 reviews

PERFECTOCEAN FRONT/PRIVATE ELEVATOR/DOCK/HEAT POOL

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

Townhouse rentals with a patio

Top guest favourite

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

The exterior of a spacious duplex is shown, featuring a light-colored façade and a wraparound porch with white railings. Lush greenery surrounds the property, and a small pool is visible in the foreground. Bright blue skies and scattered clouds complement the tropical setting.

4.86 out of 5 average rating, 7 reviews

Bayside Paradise

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, 123 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

Top guest favourite

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

A bright and inviting exterior view captures the charming two-story townhome nestled among tropical foliage. A white picket fence surrounds the property, and the entrance features double doors flanked by decorative plants. Sunlight bathes the scene, enhancing the serene outdoor environment.

4.85 out of 5 average rating, 102 reviews

Location Location Beach Paradise in the Keys Duval

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.