Townhouse holiday rentals in Key West

A bright living area features large glass doors that open to a scenic view of the Gulf of Mexico. Lush potted plants add life to the space, while natural light illuminates the wood flooring and cozy seating arrangement.

4.88 out of 5 average rating, 8 reviews

Waterfront Luxury Villa (62) with sunset views and boat slip

This premier unit and spacious 3-bedroom, 3.5-bath Villa offers Gulf sunset views from the porch and balcony. It is one of the most renovated units at Indigo. Each bedroom has its own TV, plus a large flat-screen in the living room. Private boat dock accommodates vessels up to 35’ in length, draft not exceeding 3’. Boaters insurance required. Multiple vessels or personal watercraft are not allowed in a single dock space. Accommodates up to 6 guests (Note: Minimum weekly rental. Stairs required.)

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.

4.91 out of 5 average rating, 296 reviews

Comfortable, clean, beautiful home Nov. Specials

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.

4.82 out of 5 average rating, 173 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, 148 reviews

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

*PLEASE NOTE* Villa slips/canal are under construction until Dec 2025. 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.

4.83 out of 5 average rating, 150 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.

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.

4.86 out of 5 average rating, 116 reviews

Waterfront Duck Key Villa - Sleeps 8 (7058)

BEST VIEW IN DUCK KEY!!!! Waterfront Villa at the heart of the Florida Keys - Duck Key Florida. Beautiful location with easy access to both the Atlantic Ocean and the Gulf of Mexico. Come check us out and see for yourself what the exclusive Duck Key area has to offer. DOCK INCLUDED-35 Foot. Conveniently behind the village! The Village at Hawks Cay Villas by KeysCaribbean are not affiliated with the Hawks Cay Resort; our guests do not have access to hotel amenities.

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, 207 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, 164 reviews

2B/2.5B Villa and 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.

The living area features an open layout with large windows and double French doors, allowing for ample natural light. Comfortable seating options include a plush sofa and an armchair. A large flat-screen TV is positioned on a white media console, complimented by tropical decor elements.

5 out of 5 average rating, 5 reviews

Caribbean Charm at The Foundry - Villa Near Duval

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. ** The sound of steel drums, the warm breeze off the water, the palm trees rustling in the sky… the essence of the Caribbean awaits in Key West for your next private vacation. This classic island townhome is located within Truman Annex, Key West's most exclusive gated community.

Top Guest favourite

A scenic view of the waterway is visible from the balcony, showcasing lush greenery and palm trees lining the shore. Clouds drift lazily in the blue sky, and a sailboat is anchored nearby, contributing to the tranquil waterfront setting.

4.97 out of 5 average rating, 181 reviews

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

***A quick update regarding the property. The community has scheduled construction to begin on the seawall in our backyard. At this time, work has not yet started, but a temporary fence has been placed at the back of the property for safety. The view from the home is still beautiful, and we do not currently know the exact start date for construction or if/when there may be any noise. We will keep you informed of any changes as soon as we learn more.

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, 144 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, 12 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.

Popular amenities for Key West townhouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly townhouses

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

A crystal-clear pool is surrounded by lush tropical palm trees, lounge chairs, and umbrellas. The calm water reflects a clear blue sky, creating a serene atmosphere. This outdoor space offers ample seating for relaxation, with the ocean visible in the background.

4.78 out of 5 average rating, 32 reviews

Manatee Quay-2 Canal waterfront,access BEACH club

A spacious living area features a light grey sofa and a round coffee table with a wire design. A large wall-mounted TV is positioned above a white cabinet. Natural light floods the room through windows adorned with white blinds, enhancing the open feel of the space.

4.75 out of 5 average rating, 4 reviews

Tropical 2BR | Pool | Deck | W/D

4.91 out of 5 average rating, 11 reviews

A serene waterfront view captures the modern multi-story building surrounded by lush greenery. The calm water reflects the clear blue sky, while a private wooden dock extends into the water, providing an inviting entrance to the property.

Townhouse in Islamorada

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

Top Guest favourite

An expansive oceanfront balcony showcases unobstructed views of the tranquil waters and gentle waves. The horizon is adorned with soft pastel colors from the sky, reflecting the serenity of the surroundings. A white railing frames the scene, enhancing the feeling of openness.

Townhouse in Islamorada

5 out of 5 average rating, 13 reviews

Panoramic Oceanside Luxury, Dockage & Gameroom

Aerial view of a tropical resort surrounded by turquoise waters. Cozy beach areas with sun loungers and palm trees can be seen, along with a large swimming pool. The resort's buildings are nestled amid lush greenery, creating a harmonious blend with the landscape.

4.67 out of 5 average rating, 9 reviews

Tropical Villa with Boat Slip

A wooden dock extends into clear waters, surrounded by soft sandy shores. The sky is bright with fluffy white clouds, reflecting a peaceful coastal atmosphere. The gentle waves lap against the dock, inviting relaxation and exploration.

Townhouse in Layton

4.83 out of 5 average rating, 12 reviews

Florida Keys Getaway w/ Stunning Ocean Views

Townhouse rentals 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, 67 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.

4.86 out of 5 average rating, 80 reviews

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

Aerial view of the townhouses in Harbor Village, showcasing their proximity to the canal. Lush greenery and colorful landscaping surround the buildings. Several boats are docked nearby, and parking spaces are visible in the foreground.

4.74 out of 5 average rating, 107 reviews

Waterfront Duck Key Villa - Sleeps 6 (7026)

An open living area is depicted, featuring a light-colored sectional sofa paired with earthy green accents. The kitchen area, equipped with wooden cabinetry and bar seating, is visible in the background. Natural light fills the space through large windows, enhancing the warm, inviting atmosphere.

4.78 out of 5 average rating, 23 reviews

TortugasHarbor Light Suite

A spacious saltwater pool is surrounded by tropical palm trees and a lush landscape. Sun loungers with blue umbrellas are positioned along the pool's edge, providing shaded seating for relaxation. Light dances on the water's surface under clear blue skies.

4.93 out of 5 average rating, 243 reviews

Spotlessly clean 3 bedroom/3 bathroom family home

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, 6 reviews

Forever Views

4.4 out of 5 average rating, 15 reviews

It’s all Here

A light and airy living space features a comfortable sofa with striped upholstery, positioned beside a wooden coffee table. A large artwork of ocean waves adorns the wall, while French doors open to a deck with expansive views of the Gulf waters.

4.71 out of 5 average rating, 31 reviews

PURE LUXURY - Indigo Reef 66 Gulf View & Dockage

Townhouses with a patio

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

New place to stay

2 BR - Water View Hawks Cay 5099 - Tranquil Escape

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, 82 reviews

Duck Key *Delight* private plunge pool

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.

4.95 out of 5 average rating, 20 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, 3 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.

4.83 out of 5 average rating, 89 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.