Villas and Vaction Homes in Florida Keys, FL

Located in Marathon, this luxury waterfront villa boasts a 31' dock with sea views and is an 8-minute walk from Florida Keys Aquarium Encounters and one mile from Captain Hook S Marina Dive Center.
This 1600 sq ft holiday home features 3 bedrooms, 2 bathrooms, and accommodates up to 15 guests, offering a swimming pool, spa center, fitness center, and on-site parking.

This welcoming villa in Marathon is a short walk from Coco Plum Beach and 1.2 miles from A Deep Blue Dove Center.
Offering 2050 square feet of living space, this holiday home accommodates up to 19 guests with 4 bedrooms and 4 bathrooms, featuring a private pool, spa, and year-round outdoor swimming pool.

Directly on the oceanfront in Islamorada's Matecumbe neighborhood, this cottage offers breathtaking views and is just a short distance from the History of Diving Museum and Keys History & Discovery Center.
This welcoming holiday home, perfect for four guests, features a private boat dock, complimentary kayaks and bicycles, and on-site BBQ areas, making it an ideal base for exploring this island paradise.

Directly on Florida Bay in Matecumbe, Islamorada, this cottage offers protected dockage and is less than 1 mile from John Pennekamp Coral Reef State Park and Robbie's Marina, providing a private, gated one-acre tropical setting.
This welcoming villa comfortably accommodates 4 guests with 1 bedroom and 2 bathrooms, featuring a unique ground-floor layout, air conditioning, a full kitchen, a terrace with panoramic bay views, and access to extensive outdoor relaxation areas including a sunning peninsula and tiki hut.

Located in a peaceful district of Marathon, this tranquil retreat offers a serene escape with convenient access to local attractions.
This welcoming 3200 sq ft villa accommodates up to 10 guests with 4 bedrooms and 4 bathrooms, featuring a kitchen with essential appliances, air conditioning, a swimming pool, terrace, garden, and parking.

Directly on Cudjoe Bay with ocean access via a private launch and dock, this cottage is located in Cudjoe Key, approximately 20-23 miles from Key West, offering incredible sunset views and proximity to Looe Key Reef and Bahia Honda State Park.
This 1090 square foot holiday home features 2 bedrooms and 2 bathrooms accommodating up to 4 guests, with a well-equipped kitchen, air conditioning, and a private boat ramp suitable for boats up to 24-30 feet, perfect for exploring the surrounding waters.

This waterfront spa villa in Hawks Cay, Florida Keys, is conveniently situated between Marathon and Islamorada, offering canal views and easy access to resort dining and activities like Calm Waters Spa and Dolphin Connections.
Enjoy a private plunge pool/spa on the patio, an open-concept living space, and accommodations for up to 6 guests across two bedrooms and three bathrooms, including a master with a canal view and a second bedroom with a private balcony, making this an ideal holiday home.

Located in Summerland Key, this cottage offers convenient access to Cudjoe Key and is approximately 30 miles from Key West and Bahia Honda State Park, with Sombrero Beach also nearby.
This welcoming 600 sq ft holiday home accommodates up to 4 guests and features a private covered backyard porch with patio furniture and a gas grill, plus access to community amenities including a saltwater swimming pool and tennis courts, making it an ideal villa for exploring the Florida Keys.

Located in Islamorada's exclusive oceanfront gated community of Angler's Reef at Mile Marker 84, this villa offers direct Atlantic Ocean access and is just steps from two private beaches, one with provided kayak and paddleboard equipment.
This welcoming beach house boasts 1380 square feet of living space with 2 bedrooms accommodating up to 6 guests, featuring a heated community pool overlooking the ocean, stainless steel appliances, granite countertops, and is conveniently close to renowned restaurants and watersports.

The Sea Shell Cottage UNIT #2 is located on Summerland Key, 25 miles from Key West's dining and nightlife, and a 2-minute walk to Tonio's Seafood Shack & Tiki Bar, offering convenient access to boat ramps and nearby marinas.
This welcoming 1-bedroom, 1-bathroom cottage accommodates 2 guests and features an efficiency kitchen, air conditioning, WiFi, and complimentary use of resort amenities including a communal outdoor pool and gas grill, making it an ideal holiday home for exploring Bahia Honda State Park, just a 15-minute drive away.

Directly on Sombrero Beach, this four-bedroom villa offers exclusive access to a premier Marathon destination, just 500 feet from the sand and within 5 miles of Florida Keys Aquarium Encounters and Seven Mile Bridge.
This expansive 1680 sq ft holiday home comfortably accommodates 14 guests with a private swimming pool, private dock, fully equipped kitchen, air conditioning, and complimentary WiFi, ensuring a memorable stay.

Located in Cudjoe Gardens, this waterfront vacation home is situated just 17 miles from Key West, offering direct boating access to the Atlantic Ocean and Gulf.
This spacious 3,500 sq. ft. ground-level villa accommodates up to 10 guests and features a private suite with a second kitchen, an expansive covered waterfront porch with seating and a fire table, a waterfront deck with a fish-cleaning station and grill, and a private garden with a unique bamboo-enclosed outdoor shower.

Just 500 feet from Sombrero Beach, this waterfront duplex in Marathon offers a prime location with a shared dock accommodating up to a 30-foot boat, making it an ideal beach house for anglers and boaters.
This spacious 1770 sq ft villa comfortably sleeps 10 guests with 4 bedrooms and 3 bathrooms, featuring a private heated pool, complimentary bikes and kayaks, and two covered parking spots suitable for vehicles and boat trailers.

Oceanfront on Summerland Key, this cottage is a short 20-mile drive from Key West and offers direct access to a dock and seawall, providing an ideal beach house experience.
This welcoming villa boasts 390 square feet with a full kitchen, air conditioning, and a screened patio, accommodating up to 2 guests with on-site coin laundry and a swimming pool just steps away.

Oceanside, this 1-bedroom, 2-bathroom seaside getaway villa is located in Marathon, offering direct access to the coast and is a short 11-minute walk from Florida Keys Aquarium Encounters.
This holiday home provides an outdoor pool, a fully equipped kitchen with a dishwasher and oven, air conditioning, complimentary WiFi, on-site parking, and accommodates up to 6 guests with 800 square feet of floor area.

Directly on the water in Key Largo, the Diving Capital of the World, this oceanside townhouse is located at mile marker 100 within a secure, gated community offering 24-hour security and direct access to a private marina with a deep-water dock, ramp, and trailer storage, perfect for boaters.
This beautifully decorated, fully furnished 3-bedroom, 3-bathroom villa spans 1000 square feet over 3 floors, comfortably sleeping up to 10 guests with resort-style amenities including pools, tennis courts, a playground, BBQ areas, complimentary bicycles and kayaks, and a golf cart for stays of 7 nights or longer, all while providing a lushly landscaped saltwater lagoon with a sandy beach just steps away, making it an ideal beach house for your holiday home getaway.

Centrally located in Marathon, this villa is just a 15-minute drive to Sombrero Beach and less than a 5-minute drive to the Dolphin Research Center, with convenient access to local dining and bars.
This 1800 sq ft holiday home accommodates up to 6 guests with 3 bedrooms and 2 spa-like bathrooms, featuring a newly renovated backyard with a heated inground pool and hot tub, complimentary kayaks and bikes, a fully stocked kitchen with premium appliances, and a downstairs entertainment area for group fun.

Located in Venture Out on Kemp Channel, this cottage is situated in the Lower Keys, approximately 20 miles from Key West and close to Marathon, offering accessible boating to the backcountry and a quick ten-minute ride to the open Atlantic and Looe Key National Marine Sanctuary.
This welcoming villa, accommodating up to 4 guests, features a fully equipped kitchen, air conditioning, a swimming pool, and a spacious porch with a dining area, ideal for enjoying open water views and proximity to the resort's marina amenities.

Directly on a canal in Duck Key, this waterfront villa offers shimmering water views and is a convenient 2-minute walk to Duck Key Marina, Sole Watersports, and Calm Waters Spa.
This 930 sq ft holiday home features 2 bedrooms, 2 bathrooms, a private pool, and a queen sofa bed, accommodating up to 6 guests with complimentary WiFi and provided kayak and paddleboard for immediate water adventures.

Located in Marathon, this villa is an 11-minute walk from Florida Keys Aquarium Encounters and 1.1 miles from Captain Hook S Marina Dive Center.
This welcoming holiday home offers 800 square feet of living space with 1 bedroom, a living room, a fully equipped kitchen, and 2 bathrooms, plus an outdoor pool and complimentary on-site parking.