Villas and Holiday Homes in Florida Keys

Located in Summerland Key, this cottage offers a waterfront position in the Florida Keys, just 32 kilometres from Key West, providing excellent access to attractions and natural beauty.
This holiday home, accommodating up to four guests, boasts two queen bedrooms, a full kitchen, air conditioning, and direct access to a swimming pool, dock, and seawall, making it a superb choice for a family villa rental.

This exclusive oceanfront villa in Marathon boasts a prime location with direct sea views and a private 38-foot boat slip, situated just 6.4 kilometres from Florida Keys Aquarium Encounters and 3.9 kilometres from Seven Mile Bridge.
Offering a spacious 279 square metre floor area, this family-friendly holiday home accommodates up to 23 guests with five bedrooms, four bathrooms, a private fenced swimming pool, an on-site bar, and a sun terrace, providing a luxurious beach house experience.

Located in Summerland Key, this Flamingo Cottage is just 40 kilometres from Key West and a mere 2-minute walk to Tonio's Seafood Shack & Tiki Bar.
This 1-bedroom, 1-bathroom villa rental accommodates up to 4 guests and offers a welcoming communal outdoor pool, a covered patio with grilling facilities, and beach essentials, with one dog permitted upon prior approval for an additional cleaning fee.

KAWAMA L1 is a beachfront villa in Key Largo, offering direct access to a private beach and situated 7.2 kilometres from John Pennekamp State Park and 7.4 kilometres from Dolphin Cove.
This spacious holiday home boasts air conditioning, 3 bedrooms, 3 bathrooms, and a fully equipped kitchen, alongside on-site amenities like a swimming pool, tennis court, and free bikes, with opportunities for fishing and snorkelling nearby.

This family-friendly cabin in Marathon boasts an excellent location with on-site boat launch and trailer parking, perfect for water sports enthusiasts.
Boasting 2 bedrooms and 1 bathroom, this villa rental accommodates up to 4 adults and 2 children, offering a full kitchen, air conditioning, a deep swimming pool, a private pickleball court, and complimentary bikes, kayaks, and paddleboards, alongside tiki huts with grills.

This beachfront villa in Key Largo offers exclusive access to a private beach area and is situated approximately 7.2 kilometres from John Pennekamp State Park and 7.4 kilometres from Dolphin Cove.
Enjoy this spacious holiday home, featuring 3 bedrooms, 3 bathrooms, and a capacity for 15 guests, complete with a swimming pool, on-site tennis court, and barbecue facilities, ensuring a memorable stay.

Boasting an oceanside location in Marathon, this pet-friendly smart home is just an 8-minute walk from Florida Keys Aquarium Encounters and 18 minutes on foot from Captain Hook's Marina Dive Center, with Bahia Honda State Park located 25.75 kilometers away.
This 96 square meter villa rental offers 2 bedrooms and 2 bathrooms, featuring smart home technology, air conditioning, and a kitchen equipped with a fridge, freezer, and microwave, plus on-site parking and complimentary Wi-Fi, alongside paddle equipment for SUPs and kayaks to enjoy the surrounding waters.

Located in Cutler Bay, this spacious holiday home is situated 17.7 kilometres from Fruit Spice Park and 25.7 kilometres from Miami International Airport.
This welcoming villa offers 186 square metres of living space with 4 bedrooms and 2 bathrooms, accommodating up to 23 guests, and features a dedicated games room and extensive outdoor amenities including a garden, bar, and patio for enjoyable gatherings.

Directly on Florida Bay at Mile Marker 82.2, this Islamorada cottage offers panoramic bay views and is within 1 kilometre of John Pennekamp Coral Reef State Park and Robbie's Marina.
This family-friendly villa rental boasts a private ground-floor layout with a central living area, separate sleeping quarters, an enclosed sunroom that functions as a second bedroom, and exclusive access to a sunning area with hammocks and a tiki hut, perfect for a relaxing holiday home experience.

Directly on the waterfront in Marathon, this luxury villa rental is situated between 5.1 and 5.6 kilometres from the Florida Keys Aquarium Encounters, Seven Mile Bridge, and Captain Hook's Marina Dive Centre, offering direct sea views from its terrace and 35-foot dock for boaters.
This spacious 3-bedroom, 3-bathroom holiday home accommodates up to 15 guests and features a year-round outdoor pool, children's playground, hot tub, on-site concierge, and private parking, all within easy reach of local attractions.

This luxurious waterfront villa in Key Colony Beach boasts a private 35-foot dock and direct beach access, just a 5-minute walk from Sunset Park Beach and 2.2 kilometres from Florida Keys Aquarium Encounters.
Offering 234 square metres of living space, this spacious holiday home accommodates up to 15 guests across 4 bedrooms and 4 bathrooms, featuring a year-round outdoor pool, air conditioning, and a fully equipped kitchen.

Prime waterfront villa in Marathon, this luxury holiday home boasts a 30-foot dock and is conveniently situated just a 10-minute walk from Coco Plum Beach and 1.6 kilometers from A Deep Blue Dive Center.
This exclusive accommodation offers 187 square meters of living space, featuring 3 bedrooms and 3 bathrooms to accommodate up to 15 guests, complete with a private swimming pool, hot tub, spa, and complimentary kayaks and bikes for exploring the local area.

Located in Marathon, this luxury villa offers exclusive access to a private outdoor swimming pool and spa centre, situated 2.6 miles from Seven Mile Bridge and 3.9 miles from Florida Keys Aquarium Encounters.
This spacious holiday home, spanning 222 square meters, accommodates up to 12 guests with 5 air-conditioned bedrooms, a well-equipped kitchen, and a terrace with sea views, complemented by a children's playground and complimentary on-site parking.

Located in Miami, this country walk villa is situated 16 kilometres from Fruit Spice Park and 24 kilometres from the University of Miami.
This spacious 130 square meter holiday home offers 5 bedrooms, 3 bathrooms, a private heated swimming pool, a garden, and a tennis court, perfect for a family getaway with complimentary WiFi and parking.

This luxury waterfront villa in Marathon boasts a 45-foot dock and is conveniently situated 5.6 kilometres from Florida Keys Aquarium Encounters and the iconic Seven Mile Bridge.
Offering 185 square metres of living space with four bedrooms and four bathrooms, this holiday home comfortably accommodates up to 19 guests and features a private outdoor swimming pool, a fully equipped kitchen, complimentary Wi-Fi, and on-site parking.

Centrally located in Key Colony Beach, this villa is 84 kilometres from Key West International Airport, 3 kilometres from Florida Keys Aquarium Encounters, and 29 kilometres from Bahia Honda State Park.
This welcoming three-bedroom villa rental offers 121 square metres of living space for up to 11 guests, boasting a private beach area, swimming pool, hot tub, fitness centre, and bar facilities for an exceptional holiday experience.

Offering direct kayak access for exploring local waterways, this welcoming villa in Marathon is conveniently located 3.6 kilometres from Florida Keys Aquarium Encounters, 3.9 kilometres from Captain Hook's Marina Dove Center, and 6.9 kilometres from the iconic Seven Mile Bridge.
This spacious 102 square metre holiday home, accommodating up to 15 guests, features three bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a year-round outdoor swimming pool with a tiki hut, and free WiFi.

Offering expansive open water views and a 17' seawall overlooking a 60' wide canal, this waterfront cottage in Summerland Key is located approximately 32 kilometres from Key West within a secure, 24-hour gated community.
This family-friendly villa rental, accommodating up to six guests, boasts a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, terrace, garden, and tennis court, with convenient access to water activities like jet skiing and kayaking, and proximity to Florida Keys Beaches and Coupon Bight Aquatic Preserve.

Directly on a 4-acre saltwater lagoon in Key Largo, this waterfront villa offers direct ocean access via a 1,000-foot jetty, perfect for fishing and enjoying sunsets, and is situated close to tennis courts and a playground.
This exceptional holiday home provides 150 square meters of living space for up to 8 guests, featuring 3 bedrooms, 3 bathrooms, free WiFi, air conditioning, a private dock, a boat ramp, and complimentary use of kayaks, paddle boards, fishing gear, snorkelling equipment, and bikes, alongside access to two swimming pools and three private beaches.

This canal-front villa in Cudjoe Key offers a 35-foot private dock and is within easy walking distance of Venture Out's extensive amenities, including a swimming pool, hot tub, marina, and tennis courts.
This 79-square-meter holiday home, accommodating up to six guests across two bedrooms and two bathrooms, features air conditioning, a well-equipped kitchen with a dishwasher, and two porches with water views, placing it conveniently close to Summerland Key beaches and aquatic preserves.