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Villa vacation rentals in Grassy Key

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Top-rated villa rentals in Grassy Key

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A bright and spacious living area features a large dining table with wooden chairs and a central coffee table. Soft seating is arranged around a sliding glass door that opens to the outdoor patio. Decorative curtains frame the windows, enhancing natural light.

Villa in Duck Key

4.96 out of 5 average rating, 91 reviews

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.

Top guest favorite

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

Villa in Marathon

4.95 out of 5 average rating, 145 reviews

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!

A private pool is surrounded by a spacious patio featuring lounge chairs and an umbrella. Lush palm trees provide shade, while a barbecue area and bicycles can be seen in the background, enhancing the outdoor living space.

Villa in Marathon

5 out of 5 average rating, 15 reviews

Waterfront Home w/Dock, Pool, Bikes & SO MUCH MORE

Looking for the perfect home for your next Florida Keys vacation? Our Waterfront home with over 30 feet of dock space is Just a short boat ride out to open water for a day of fishing, snorkeling, or cruising around. Our home features your own private dock & private pool... complete with chaise lounges, outdoor dining, gas grill, Adirondack chairs, fish cleaning station, bait freezer & so much more! Lastly, everyone is sure to enjoy water views & sunsets from our balcony that never disappoint.

A shaded outdoor deck features a circular wooden table surrounded by six chairs. A ceiling fan hangs above, and views of the water and surrounding trees are visible through the railing. The tranquil scene is highlighted by the soft blue sky.

Villa in Marathon

4.79 out of 5 average rating, 99 reviews

Villa 7075 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, NO pets.

A serene beachfront area is presented with several white lounge chairs facing the tranquil blue waters. Rocky shoreline and greenery outline the space, creating a peaceful environment for relaxation.

Villa in Key Largo

4.92 out of 5 average rating, 115 reviews

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.

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

Villa in Duck Key

4.95 out of 5 average rating, 148 reviews

Beach House - Kayaks & 2/2.5 Villa

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.

A newly built house in a bright mint color is set amidst tropical greenery. The structure features a spacious covered porch with white railings. A gravel driveway provides ample parking space, with a truck parked nearby, under a partly cloudy sky.

Villa in Marathon

5 out of 5 average rating, 11 reviews

Villa Marlin - Perfect Vacation in Florida Keys

Spacious house, newly built with a private outdoor pool in the beautiful Florida Keys. This is the perfect location for boating enthusiasts. There is space for both parking and boat trailers. An exclusive ramp is a block away (30-second drive or 1-minute walk), leads to Gulf of Mexico, and 10 minutes to the Atlantic Ocean. A pool heater is provided for free for renters during the Winter. Outdoor pool shower included. Barbecue gas always provided. Games include corn hole, domino, billard.

Aerial view of the Indigo Reef gated community, showcasing rows of villas surrounded by lush greenery. Crystal-clear waters are visible, with docks leading to the ocean. The vibrant blue sky extends over the scene, reflecting the peaceful coastal environment.

Villa in Marathon

5 out of 5 average rating, 12 reviews

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. 31' 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

A private hot tub sits on the rooftop terrace, surrounded by a white railing. Lush greenery fills the foreground, while a view of the Gulf coast extends towards the horizon under a clear blue sky.

Villa in Marathon

4.93 out of 5 average rating, 15 reviews

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! TWO private hot tubs ensure you can star gaze on the rooftop or come home from a run or bike ride and go straight for a hot 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 beach area and two private parking spots.

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

Villa in Marathon

4.9 out of 5 average rating, 340 reviews

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!

A two-story house is set against a clear blue sky, featuring balconies and a light blue exterior. A wooden dock extends into tranquil water, with paddleboards and kayaks visible. A heated pool is surrounded by palms, offering a relaxing outdoor space.

Villa in Marathon

5 out of 5 average rating, 3 reviews

Marathon Villa w/ Priv Pool/Dock

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!

An expansive pool area features a large, curvy swimming pool surrounded by palm trees. Comfortable lounge chairs are arranged around the pool, and a smaller hot tub is situated nearby. The carefully landscaped grounds incorporate pathways and shaded cabanas for relaxation.

Villa in Key Largo

5 out of 5 average rating, 17 reviews

4BR Villa in Key Largo w/ Marriott Amenities

Discover a serene vacation rental where luxury meets tranquility. Ocean Residences offers modern design, a secluded retreat vibe, and access to the exclusive amenities of Playa Largo Resort & Spa, including pools, dining, and beachside relaxation (wristband required). Pet-friendly with a stunning clubhouse and Atlantic views, this destination ensures unforgettable memories. Complimentary shuttle service makes exploring effortless. Book your ultimate getaway today!

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Popular amenities for Grassy Key villa rentals

Free parking on premises

Air conditioning

Private villa rentals

A serene waterfront scene is depicted, featuring paddle boards laid along a grassy area beside a concrete pathway. Palm trees and a sunset over the water contribute to the natural beauty, while boats are visible in a nearby dock.

Villa in Islamorada

5 out of 5 average rating, 4 reviews

The Nest Villa & Marina in the heart of Islamorada

The view from the patio showcases a vibrant sunset reflecting on the tranquil water. Lush palm trees frame the scene, with the illuminated pool area visible below. A distant pier extends into the water, enhancing the serene ambiance of the location.

Villa in Marathon

4.75 out of 5 average rating, 157 reviews

Sunset Villa in Duck Key

A spacious living area features a modern design with light-toned wood flooring. Comfortable seating arrangements face a wall-mounted TV, while a dining table accommodates several guests. Large windows allow natural light to fill the room, offering views of the outdoor space and greenery.

Villa in Key Largo

4.75 out of 5 average rating, 8 reviews

Oceanfront 4BR Villa w/ Pool & Resort Access

An aerial view captures a large pool surrounded by vibrant palm trees and comfortable lounge chairs. The pool features a curvy shape, with a section for swimming and areas for relaxation, showcasing a blend of greenery and water in a tranquil setting.

Villa in Key Largo

4.68 out of 5 average rating, 19 reviews

Spacious 4BR Villa: Pool, Clubhouse & Gym

Top guest favorite

A private swimming pool reflects the clear sky, surrounded by lush tropical landscaping. Lounge chairs are positioned on a wooden deck, providing a relaxing area near the pool. The home's exterior features multiple balconies, framed by palm trees and vibrant foliage.

Villa in Duck Key

4.99 out of 5 average rating, 76 reviews

Duck Key *Bliss* Private Pool & Patio

An aerial view reveals a spacious swimming pool surrounded by lounge chairs and palm trees. The pool features a curved shape and is situated amidst manicured landscaping, creating a relaxing oasis. A nearby area showcases additional seating and pathways, enhancing the tranquil ambiance.

Villa in Key Largo

4.63 out of 5 average rating, 8 reviews

Key Largo Villa | Gym, Pool & Beach Access

A tranquil canal scene is displayed, featuring wooden docks lined with boats. Lush greenery surrounds the waterway, contrasted by clear blue skies. The inviting area suggests accessibility for water activities such as snorkeling and scuba diving.

Villa in Key Largo

Spacious Villa w/ Boat Slip

A comfortable living area features a gray sofa and a wicker chair, complemented by an orange accent wall. Large sliding doors provide access to an outdoor space, allowing natural light to fill the room. Neutral-toned tile flooring enhances the inviting atmosphere.

Villa in Marathon

4.59 out of 5 average rating, 17 reviews

Key Lime Cottage - Lovely Duck Key Villa, Dip Pool

Luxury villa rentals

A two-story villa features a cheerful yellow exterior, showcasing a spacious front porch with white railings. Lush green landscaping surrounds the entrance, with vibrant plants adding color. The well-maintained structure stands alongside other similarly styled homes in a serene and inviting neighborhood.

Villa in Islamorada

5 out of 5 average rating, 36 reviews

Anglers Reef Islamorada

Top guest favorite

A serene outdoor seating area features two white Adirondack chairs set around a round table. A glass of white wine and a cocktail sit on the table, accompanied by a book. A vibrant pillow with an anchor design rests on one chair, with views of lush greenery and the water beyond.

Villa in Marathon

5 out of 5 average rating, 22 reviews

Indigo Reef water view Villa- #1 Guest Favorite

A sparkling pool is set against a backdrop of lush greenery and calm water. A hammock is suspended between palm trees, inviting relaxation. Surrounding the pool, well-maintained landscaping features vibrant plants and manicured grass, enhancing the serene outdoor space.

Villa in Marathon

4.75 out of 5 average rating, 4 reviews

Villa Sombrero

A spacious dining area features a long wooden table paired with matching benches. Bright artwork adorns the white walls, while a chandelier hangs above. Large glass doors open to a view of the outdoor space, allowing natural light to fill the room.

Villa in Marathon

5 out of 5 average rating, 11 reviews

Harbor hideaway 50’dock 3Br/2Ba All amenities

A private outdoor terrace is shown with wooden flooring and a large ceiling fan. Two white chairs face a stunning sunset over lush greenery, with soft light illuminating the scene. The balcony railings feature a classic design, enhancing the serene waterfront view.

Villa in Islamorada

5 out of 5 average rating, 3 reviews

Bayberry Key: FREE Boat Dockage Sep-Oct Only!

A two-story structure with a light-colored exterior is framed by well-maintained greenery. The front porch features a railing and is flanked by palm trees, creating a welcoming entrance. Large windows allow natural light to enter the home.

Villa in Islamorada

4.9 out of 5 average rating, 20 reviews

Islamorada house with best location. Lic # 24-0055

The two-story villa presents a light green exterior with multiple large windows, allowing natural light to enter. Elevated on stilts, ample space underneath offers shade, while the stairway leads to the main entrance. Architectural details emphasize a welcoming coastal style.

Villa in Marathon

4.88 out of 5 average rating, 59 reviews

New Paradise On Sombrero Beach

A covered porch features four white Adirondack chairs positioned on a wooden deck. Lush green palm trees and landscaping provide a tropical backdrop, while a sparkling pool is visible in the distance, completing the serene outdoor setting.

Villa in Marathon

5 out of 5 average rating, 10 reviews

Waterfront Villa (38) w/ sunset views & boat slip

Villa rentals with a pool

The living area features a comfortable gray sofa and a patterned armchair surrounding a wooden coffee table. Sliding glass doors provide access to the pool area, allowing natural light to fill the room and offering views of the lush greenery outside.

Villa in Duck Key

4.38 out of 5 average rating, 21 reviews

2BR water view with private pool, balcony & kayak

A spacious outdoor area features a private pool surrounded by a wooden deck. Loungers invite relaxation under the shade of palm trees. The home, with two stories, showcases a covered patio equipped with dining furniture, complemented by lush greenery for added privacy.

Villa in Duck Key

5 out of 5 average rating, 7 reviews

Florida Keys Sanctuary

Two comfortable white Adirondack chairs are positioned on a wooden deck, overlooking a lush green lawn and palm trees. A canal with a boat can be seen in the background, completing the serene waterfront view.

Villa in Marathon

Luxury Waterfront Villa, Marathon, Florida Keys

Villa in Key Largo

4.86 out of 5 average rating, 51 reviews

2bd/2ba Ocean Retreat in Kawama Yacht Club

A spacious bedroom features a wooden bed frame with a plush white comforter. Decorative pillows add a touch of color against a soft green accent wall. A bedside lamp and a wooden side table complement the cozy atmosphere.

Villa in Islamorada

4.68 out of 5 average rating, 59 reviews

Picturesque Villa Near History of Diving Museum

An aerial view captures a marina community surrounded by lush greenery and clear blue waters. The scene includes multiple townhomes lined along the waterfront, with boat slips visible along the shoreline. A resort-style pool can also be seen in the center of the community.

Villa in Marathon

Refreshed & Elevated Indigo Reef Luxury Villa 15,

A private pool is surrounded by a paved patio, featuring comfortable lounge chairs and large umbrellas for shade. Nearby, a hammock is suspended between two posts, and tropical greenery provides a natural backdrop. The area is well-lit by natural sunlight.

Villa in Marathon

"Keepin’ It Reel" Waterfront, 4BD/3BA FL Keys Home

An aerial view of the villa displays a private pool surrounded by lush greenery and paved patio. The building features bright white exteriors and multiple balconies, with seating areas visible on the patio. A tranquil canal runs alongside the property, enhancing the outdoor living space.

Villa in Marathon

4.74 out of 5 average rating, 35 reviews

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