Villa holiday rentals in Grassy Key

Isla Luna ~ Waterfront Oasis ~ Pool ~ Dock ~ Kayaks

Indulge in this luxurious 4BR 4BA estate nestled on a gorgeous waterfront property in Marathon, FL. The 3-story Isla Luna offers the perfect retreat from bustling crowds with its modern design, high-end comforts, and scenic outdoors with heated pool, private dock, deck, Kayaks, Bikes, and Pac-Man arcade. ✔ 4 Comfortable BRs ✔ Open Design Living ✔ Chef's Kitchen ✔ Heated Pool ✔ Yard (BBQ, Games, Bikes, Kayaks) ✔ 42ft Dock (Fishing Station, Water) ✔ 3 Decks ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Parking

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!

Kawama Yacht Club and Molasses Reef Marine

Vacation in paradise. Beautiful sunsets. Swim at the salt water lagoon or at the beach plus two pools. Our villa is fully equipped, 3 bedrooms wish tv and 3 full baths First floor: garage, 1 bedroom, full bathroom, game room, pool table, bar, family room with TV, and terrace with barbecue and swing. Second floor 2 bedrooms and 2 full bathrooms, fully equipped kitchen and living a big TV, outside balcony with outdoor furniture . Tennis courts available. Optional 24' ft boat slip available.

Beach House Getaway - Free Kayaks 2/2.5

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

Crystal Waters - Free Kayaks 2/2.5 Coastal Villa

Escape to tranquility in this beautifully appointed villa located in the heart of Duck Key — one of the Florida Keys' most serene and scenic islands. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

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.

Marlin House (52): Luxury 3/3 Villa w/ Dock, Pool

Welcome to the Marlin House. This 3 bed 3 bath luxury villa is located in the gated community of Indigo Reef. Immediate boat access to the Gulf and Ocean. 35' dockage incl. You'll appreciate the professionally decorated open floor plan that expands through the gourmet kitchen, family room and onto the outdoor lanai. Three private bedrooms, each with decks. Enjoy happy hour and grill your catch as you watch the sunset! Free WiFi, Parking & Dockage Contact owners 24/7 for any assistance

Angler’s Reef home • Pool • Kayaks • Paddle boards

Relax with the whole family at this peaceful Angler's Reef boutique complex. Oceanfront community located at Mile Marker 85 has a beautiful community pool overlooking the Atlantic ocean. The community also offer kayaks, which can be launch from the private beach. This home has 2 bedrooms located on the 2nd floor with their private bathroom. The kitchen is fully equipped with stainless appliances, granite counters, 3 TVs & WiFi. The property has parking for 2 vehicles. License 26-5143

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!

Oceanfront Resort W/Indoor Pickleball - Speakeasy!

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. This 3/3.5 villa is located in Key Largo's most upscale oceanfront resort. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simply desire the very best in luxury accommodations. Unique amenities include a Speakeasy Themed Rec. Area.

Villa 5023 on Duck Key BOAT SLIP available

Boat slip available for additional $100 a night. 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.

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