Townhome holiday rentals in Key West

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.

4.83 out of 5 average rating, 190 reviews

Villa 5020 on Duck Key BOAT SLIP available

Boat slip available for an additional $100 per night. Ask about availability. This villa boasts breathtaking sunsets and is just minutes from watersports, charter fishing, waterfront restaurants, and local attractions, all while being surrounded by one of Duck Key’s most exclusive island neighborhoods with lush tropical landscaping. Duck Key is perfect for families or a serene couples retreat. Dine while watching spectacular sunsets from the rear deck, or explore the Middle Keys. No Smoking/Pet

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, 195 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.

Townhouse in Key Colony Beach

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.

5.0 out of 5 average rating, 14 reviews

Castillo Del Mar- Ocean access from your backyard

Welcome to PARADISE! — perfect for salty families, fishing lovers and beach goers • Prime Location – In Key Colony Beach with access to Cabana Club pool & private beach • Walk to Dining – Steps from Sparky’s Landing & Island Company • Boater’s Paradise – Backyard dockage for boats up to 30 ft • Spacious Kitchen – Family-style layout with 4-person bar top • Boho Dining Room – Perfect for cozy dinners and entertaining • Amenities include washer + dryer, fully stocked kitchen, Cozy Tv Room

A shared pool area is surrounded by lush tropical landscaping, featuring palm trees and greenery. Sun loungers and umbrellas are arranged around the pool, offering ample space for relaxation. The water reflects the clear blue sky, creating a serene and inviting scene.

4.84 out of 5 average rating, 174 reviews

Charming Key West Vacation Rental 3bedrm/3bath

Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler. Portable Crib, high chair & more. Items available upon request

Townhouse in Key Colony Beach

4.9 out of 5 average rating, 105 reviews

The Palm House in Key Colony Beach, Florida Keys

3/2 Duplex 37.5' dockage on canal in Key Colony Beach. The property's private (fenced in) back patio has a BBQ, couches and dining table/umbrella facing Eastward with morning sunshine and afternoon shade. Property includes usage of the Cabana Club, a large heated/cooled pool, hot tub, Atlantic Ocean beach and drinks/hot food just a 5 minute walk away. The concrete/wood dock has a fish cleaning station, bait freezer, water hose and gated access for the your boat. Welcome back to paradise !

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.

4.81 out of 5 average rating, 231 reviews

Vibrant Beachfront Villa

Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****

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.

4.87 out of 5 average rating, 257 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 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.

4.95 out of 5 average rating, 171 reviews

Boater’s Paradise 3br/2.5ba Villa with Slip!

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.

4.93 out of 5 average rating, 290 reviews

Spotlessly clean 3 bedroom/3-bathroom family home

Great family home in the gated community of Coral Hammock, located just 10 minutes from the center of Key West. It boasts a saltwater pool just steps away from the property. Perfect for families or groups of mature adults. All renters must be 25 or over or with a parent/guardian.

An outdoor patio area features a dining table and chairs alongside a plunge pool. Lush greenery surrounds the space, creating a private environment. A white fence provides a barrier while palm trees and a clear blue sky enhance the ambiance.

4.98 out of 5 average rating, 133 reviews

Casa Wahoo - Waterfront Retreat

Welcome to Casa Wahoo – Your Waterfront Retreat in the Heart of the Florida Keys! 🌴 A bright and breezy 2-bedroom, 2.5-bath townhouse located on beautiful Duck Key within the exclusive Hawk’s Cay Resort community. This stylish getaway comfortably sleeps up to 6 guests.

A vibrant outdoor space is surrounded by lush tropical plants and trees. A pathway leads to a light green door, with seating visible underneath a bright red umbrella. The area offers a welcoming atmosphere perfect for relaxation.

4.77 out of 5 average rating, 186 reviews

Nassau Suite just steps to Duval Tropical oasis q

Nassau Suite is a one bedroom Townhouse with a very spacious bedroom upstairs a king bed, TV. Downstairs queen sleeper in the living area and full kitchen. Parking is on street. Pool for the compound. 921 Center Street #12. Key West FL 33040. 3 NIGHT MIN

4.82 out of 5 average rating, 17 reviews

Parrotville! Townhome for weekly rental

Parrotville is part of the Windward Park gated community just off Simonton Street. This 2 bedroom, 2 bathroom townhome is surrounded by lush tropical landscaping and views of a sparkling swimming pool.

Popular amenities for townhouse rentals in Key West

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly townhouse rentals

4.97 out of 5 average rating, 30 reviews

Beautiful View! 3BR 3 BA, Cabana Club Membership!

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.

5.0 out of 5 average rating, 17 reviews

Exceptional Water View With Boat Dock!

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.

4.93 out of 5 average rating, 14 reviews

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

A wooden bridge leads through a lush garden, framed by greenery and festive decorations. A stone wall is visible at the end of the path, flanked by potted plants. Light filters softly through the nearby trees, creating a serene and inviting entryway.

4.74 out of 5 average rating, 27 reviews

Hemingway First Floor Townhouse @ Suite Dreams Inn

5.0 out of 5 average rating, 5 reviews

Sea Esta Suite | Located On Iconic Duval w/ Pool

A light-filled living area features a comfortable sofa and a wooden coffee table. Large glass doors open to a deck with outdoor seating, showcasing views of the surrounding greenery and water. Neutral tones and decorative accents enhance the inviting atmosphere.

4.82 out of 5 average rating, 90 reviews

Coral Lagoon Villa 5 With Pool and On-Site Marina

5.0 out of 5 average rating, 3 reviews

Ocean Isles #98~ Fishing Village, Community Pool!

4.78 out of 5 average rating, 51 reviews

Dockside Daydreams at Coconut Mallory

Townhouse accommodation with a washing machine and dryer

4.89 out of 5 average rating, 63 reviews

Coral Lagoon 3bd/2.5ba townhome, boat slip & pool

Townhouse in Layton

4.81 out of 5 average rating, 21 reviews

Florida Keys Getaway w/ Stunning Ocean Views

An aerial view captures the resort's well-maintained properties with silver roofs and lush greenery. The adjacent waterfront features palm trees lining a tranquil waterway, with a glimpse of a pool area in the distance, framed by the serene Gulf waters under a clear blue sky.

4.88 out of 5 average rating, 26 reviews

SUNSATIONAL 3 BR Indigo Reef with 30' Dockage

4.94 out of 5 average rating, 90 reviews

Life in Paradise in #1 Resort -Coral Lagoon w/Slip

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.

4.68 out of 5 average rating, 348 reviews

Sunset Views!

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.

4.78 out of 5 average rating, 40 reviews

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

Townhouse in Key Colony Beach

A bright living area features a comfortable sofa and armchair, complemented by a coffee table. Large sliding glass doors open to a patio area, enhancing indoor-outdoor flow. Pendant lighting fixtures hang over a kitchen bar, illuminating the countertop. Light blue walls provide a serene backdrop.

4.95 out of 5 average rating, 55 reviews

KCB Angler Retreat w/ Cabana Club access

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.

4.69 out of 5 average rating, 13 reviews

Tropical Villa with Boat Slip

Townhouse rentals with a patio

The exterior of a spacious canal-front home is presented, showcasing a light-colored structure with a screened-in porch. Lush greenery surrounds the property, and two jet skis are parked nearby. The backdrop features a clear blue sky scattered with a few clouds.

4.95 out of 5 average rating, 37 reviews

Bayside Fishing Haven, Canal Dock, Pool, Bay View

A spacious dining area features a long table surrounded by several chairs, with woven placemats arranged neatly. Decorative coastal elements, including starfish and light fixtures, complement the muted blue walls, while natural light streams in through large windows leading to an outdoor space.

4.83 out of 5 average rating, 59 reviews

The Coral Paradise

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.

4.83 out of 5 average rating, 77 reviews

Beachy Townhome Perfect For A Relaxing Getaway!

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.

5.0 out of 5 average rating, 91 reviews

Duck Key *Delight* private plunge pool

A serene view of the marina is captured, featuring clear turquoise waters and several boats docked along the pier. Lush green grass frames the scene, while a backdrop of fluffy white clouds enhances the coastal ambiance.

4.9 out of 5 average rating, 60 reviews

Majestic Marina View – 2BR/2.5BA at Hawks Cay

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.

4.89 out of 5 average rating, 18 reviews

7-Mile Bungalow

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.

5.0 out of 5 average rating, 4 reviews

Bonefish Yacht Club

A crystal clear freshwater pool is visible, framed by tropical palm trees. A thatched tiki hut provides shade nearby, under a bright blue sky adorned with scattered clouds. Surrounding fencing maintains a defined area, contributing to a serene atmosphere for relaxation.