Townhome holiday rentals in Key West

4.91 out of 5 average rating, 296 reviews

Comfortable, clean,beautiful home Summer Special

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

4.8 out of 5 average rating, 142 reviews

Townhouse in Duck Key

Villa 5103 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.

4.96 out of 5 average rating, 181 reviews

Townhouse in Duck Key

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.

4.96 out of 5 average rating, 148 reviews

Townhouse in Marathon

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.

4.83 out of 5 average rating, 149 reviews

Townhouse in Duck Key

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.

4.86 out of 5 average rating, 116 reviews

Townhouse in Marathon

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.

5 out of 5 average rating, 3 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.

4.77 out of 5 average rating, 109 reviews

Charming Key West Vacation Rental 2 Bedroom

Beautiful, gated home located in Coral Hammock just minutes away from Key West. It's a spacious 2 bedroom, 2 1/2 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. Beach Gear is also available. Beach towels, beach chairs, beach toys, floats and cooler. Please Request Baby / Toddler items available upon request. Portable Crib, high chair & more.

Top guest favourite

Townhouse in Marathon

4.97 out of 5 average rating, 180 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.

4.92 out of 5 average rating, 165 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat 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, kayaks, paddle boards and golf carts can be rented locally

Townhouse in Key Colony Beach

4.8 out of 5 average rating, 143 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.