Villa vacation rentals in Key West

Waterfront Island Escape with Private Plunge Pool

Come and relax in your own private plunge pool that overlooks a turquoise canal on the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay locally to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.

Family · Value · Solo travel

Villa 5034 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

Location · Value · Walkability

Aqua Verde ~ Waterfront Lux Gem ~ Dock ~ Game Room

Welcome to this stunning brand-new 3BR 3BA waterfront retreat in Marathon, Florida Keys. This vibrant two-story canal-front home offers the perfect blend of modern luxury and island living with its contemporary design, heated pool, game room, and private 50-foot dock with direct ocean access. ✔ 3 Spacious BRs ✔ Open Concept Living ✔ Full Gourmet Kitchen ✔ Heated Swimming Pool ✔ Game Room (Foosball, Arcade, Dominoes Table) ✔ Waterfront Yard (BBQ, Outdoor Dining) ✔ 50ft Private Dock (Fishing Stat

Family · Location · Layout

Lux Sunset Villa 15: 3BR w/ Boat Slip, Boat Ramp A

Sunset Villa is a Lux 3 BD, 2.5 BA marina home and a 31 ft dedicated boat slip located in the most exclusive townhome village on the island of Marathon in the Florida Keys. Newly remodeled to a casual coastal elegance by a professional designer, this private home shines. Sunset Villa has everything for a perfect island vacation: resort pool, 31 ft boat slip, gym, on site parking, lush grounds, and a designer villa. We also provide access to a private boat ramp and parking at a location closeby.

Location · Value · Comfort

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Location · Value · Layout

Florida Keys Wellness Gem Tranquility & Activity

Enjoy yourself in the Florida Keys in this spacious, 3 BR, 3 baths condo in Marathon, right on the Gulf coast! One private hot tub and one private plunge pool ensure you can star gaze on the rooftop or come home from a run or bike ride and go straight for a soak! The view from the rooftop is amazing, rooms are spacious and clean. Add the fully equipped kitchen, washer & dryer as well as fresh sheet service and so much more. This home also has a shared pool and two private parking spots.

Location · Family · Indoor spaces

Top guest favorite

Guest favorite

Beach House | Waterfront Villa | Free Kayaks

Wake up to beautiful water views and the laid-back charm of Duck Key. This beautifully renovated waterfront villa offers a relaxed coastal setting, comfortable living spaces, and inviting outdoor areas made for morning coffee, sunset views, and evening cocktails. Ideally located in the heart of the Florida Keys, it’s a perfect home base for boating, fishing, snorkeling, beach days, and waterfront dining, with Marathon, Key West, Islamorada, and other Keys favorites within easy reach.

Family · Location · Walkability

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Value · Family · Quiet

Top guest favorite

Guest favorite

Marathon Villa w/ Priv Pool/Dock Sombrero Beach

Marathon, Florida is in the middle of all the beauty and action of what the Florida Keys have to offer. Sombrero Beach is at a bike ride or walking distance. It offers complimentary parking, outdoor grilling, beach volleyball, children play area, and public restrooms. 40 foot dock offers guests the option to bring their boats or rent one. Our heated pool is a perfect way to soak up the tropical vibes. Kitchen is fully equipped. We are at walking distance to grocery store!

Location · Family · Nearby

Top guest favorite

Guest favorite

Duck Key Waterfront Villa w/Kayaks, near 2 Marinas

Welcome to Crystal Waters Cay, an immaculate 2BR/2.5BA villa steps from the water inside the Hawks Cay Resort area and marina! Our unique hotel designation means 1-night stays are welcome—perfect for a quick Keys escape. Enjoy two private upstairs suites, free tandem kayaks, and plenty of unassigned first-come parking. Walk to public resort highlights like the 5-star dining at Salt + Ash, waterside eats at Angler & Ale, the marina, gym, and spa. Fixed cleaning fee applies.

Family · Location · Access

Villa in Paradise. Plunge pool. Middle of the Keys

Baja Breeze 🏝, a freshly updated, family-friendly, resort-style villa in the ♥ of the Keys. ♥ Please save Baja Breeze by clicking on the heart in the top right hand corner, this will help you find it again and share with others! 🛶 Waterfront canal view 🌴 Gated Resort Area 👙 Private spa pool 📍 Halfway between Key Largo and Key West ☀️ Outdoor dining/lounge area 🍳 Fully stocked Kitchen 📶 300Mbps+ Wifi

Location · Value · Sleep quality

Coral Villa by AvantStay| Close 2 DT Key West!

Welcome to Coral Villa by AvantStay. Soft earth tones, sunlit interiors, and a quiet gated-community setting make this Key West townhome feel like a true island retreat — with Duval Street, Smathers Beach, and the airport all just minutes away. 🚗 Gated community w/ off-street parking for 2 🏌️ Across from Key West Golf Course 🏊 Shared community pool & clubhouse 🍹 Minutes from restaurants, bars & marinas

Location · Kitchen · Sleep quality