Villa vacation rentals in Grassy Key

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Popular amenities for Grassy Key villa rentals

Private villa rentals

Guest favorite
Villa in Islamorada
5 out of 5 average rating, 6 reviews

Isla Guava: Waterfront Htd Pool, Dock, Walkable

JenRating, 5 stars2 months ago
Amazing place, you can’t beat the location and property. The house was exceptionally clean and the host was very friendly and easy to communicate with. We will definitely return!!
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
4.67 out of 5 average rating, 49 reviews

Picturesque Villa Near History of Diving Museum

BethRating, 5 stars2 weeks ago
Beautiful accommodations and gorgeous grounds to relax by the ocean and pools. Highly recommend!
A modern clubhouse is framed by palm trees, featuring a spacious porch with white railings and several seating areas. A crystal-clear pool reflects the building, inviting relaxation. The setting is accented by lush greenery under a backdrop of soft clouds.
Villa in Key Largo
4.46 out of 5 average rating, 13 reviews

Guest Spring Break Stay: Resort Amenities & Views

LestrydRating, 5 stars1 month ago
Our stay at this house was absolutely perfect! The home itself was spacious, beautifully maintained, and had everything we needed for a comfortable and relaxing getaway. What made it even better was the access to the resort amenities like pools, restaurants, and activities, all just a short distance away. It truly felt like having the best of both worlds: the privacy of a home with the luxury of a resort.
A modern clubhouse is depicted with a spacious balcony and large windows, surrounded by palm trees. A refreshing pool sits in the foreground, while comfortable seating areas are visible on the deck, inviting relaxation in a serene atmosphere.
Villa in Key Largo
4.4 out of 5 average rating, 5 reviews

Spring Break Lux: 5-Star Villa w/ Marriott Access

MelissaRating, 5 stars1 month ago
We had a great stay and would definitely come back! The place was very spacious and modern and clean. Rodrigo, the host, was responsive and very helpful. Highly recommend!
A bright living room features a comfortable sofa and an armchair with decorative patterns. Light-colored walls are complemented by wood flooring. A coffee table sits in front of the sofa, and large sliding glass doors offer a view of the waterfront and patio area.
Villa in Duck Key
4.23 out of 5 average rating, 22 reviews

2BR oceanfront with amazing views, balcony & kayak

JanetRating, 5 stars2 months ago
It was quiet and comfortable. Very clean throughout. Beautiful location. Loved the decks upper and lower. I would rent again.

Luxury villa rentals

Guest favorite
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, 32 reviews

Anglers Reef Islamorada

NicoleRating, 5 stars1 month ago
Our family of 5 loved our time in Islamorada. The community was beautiful and quiet. It was definitely mostly retired couples but everyone was friendly with our young kids. The condo was bigger than the pictures made it seem- we had more than enough space. Everything was clean and we had everything we needed.
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
4.67 out of 5 average rating, 3 reviews

Villa Sombrero

NikkiRating, 5 stars28 months ago
We had a wonderful time. The neighborhood is beautiful, super quiet and nice to walk around. We used the provided paddle boards to go to nearby Sombrero Beach which was lovely. We also walked to Publix and Walgreens. The house itself is really two houses - one upstairs and one downstairs - each with their own kitchens, bedrooms and bathrooms. The house itself is simple and utilitarian, but backyard area is really spectacular. We spent the vast majority of our time outside lounging, playing tennis or swimming in the pool. The location also makes for an easy day trip to Key West. The property manager Jesús was extremely responsive and took care of everything we needed.
Top guest favorite
Villa in Marathon
5 out of 5 average rating, 21 reviews

Indigo Reef water view Villa- #1 Guest Favorite

CaitlinRating, 5 stars2 weeks ago
We absolutely loved our stay and can’t wait to return! The unit was pristine and we loved watching the sunsets from the porches. The pool was pristine and never crowded. The hosts were amazingly responsive and helpful.
Guest favorite
A modern clubhouse features a broad porch with multiple seating areas surrounded by lush greenery. A sparkling pool reflects the sky, enhancing the serene atmosphere. Palm trees frame the structure, creating a tropical vibe with clear views of the architectural details.
Villa in Key Largo
4.89 out of 5 average rating, 19 reviews

Lux Villa for Spring Break: Pool, Kayak & Marriott

KarenRating, 5 stars1 month ago
I had an amazing time around, Josie was amazing and the overall attention was great, if you want to relax and have a great time around, this is your place!
A bright bedroom features a spacious bed with a floral throw across the bottom. Light-colored walls complement the wooden ceiling. A small armchair sits in the corner, and large glass doors lead to a balcony, allowing natural light to fill the room.
Villa in Key Largo
5 out of 5 average rating, 3 reviews

Dolphin 1-Bedroom Villa

KellyRating, 5 stars37 months ago
A beautiful quiet place to stay. Kayaking in the morning and swimming in the pool at night. We loved exploring other Florida Keys and coming back to sleep. Easy check in and out.
An aerial view of a beautiful villa surrounded by lush greenery and palm trees. The property includes a private heated pool, lounge chairs, and a tiki hut, all set against the tranquil waterfront, with a boat dock visible along the edge of the water.
Villa in Islamorada
4.86 out of 5 average rating, 7 reviews

3 EnSuite Bedrooms! Waterfront Resort, Pool, Dock!

MeghanRating, 5 stars3 weeks ago
This house was perfect for our family of 5 for Spring Break. The canal at the back was perfect for fishing, kayaking and SUP. The pool was lovely and warm. The house and grounds were so beautiful and comfortable! We had a wonderful time and would stay here again in a heartbeat!
A serene marina scene is captured with boats moored on calm waters surrounded by lush palm trees. The sky displays dramatic clouds illuminated by the golden hues of sunrise, creating a peaceful coastal atmosphere.
Villa in Key Largo
4.79 out of 5 average rating, 68 reviews

Oceanfront Villa overlooking the Atlantic

ShannonRating, 5 stars25 months ago
My family really enjoyed our stay at Vivian’s place! The photos do not do it justice! Very roomy, amazing water views, and beautiful decor/upgrades. Vivian had everything we needed for our stay - we traveled with a toddler and baby and everything we needed was there. Vivian was responsive and helpful. We would definitely stay again! Thanks Vivian!
Guest favorite
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

KatrinRating, 5 stars1 month ago
Great location on the property. Beautiful view of the water and the pool. Nice big porch to relax on with plenty of chairs. Provided plenty of towels and the kitchen had everything you needed. Could have used more TB, PT and some dishwasher soap but all good. This place is a favorite of ours to just relax and go boating! Highly recommend!!

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
4.35 out of 5 average rating, 20 reviews

2BR water view with private pool, balcony & kayak

JennaRating, 5 stars2 months ago
very comfortable villa. Absolutely loved the little swimming pool. Clean and comfortable villa.
Villa in Islamorada
5 out of 5 average rating, 3 reviews

Isla Mamey: Waterfront Htd Pool, Dock, Walkable

TanyaRating, 5 stars8 months ago
Our family of 4 stayed for 11 nights to celebrate our twins 10th birthday. We live in Miami and brought most of our kitchen but totally wasn’t needed! Villa #5 has anything and everything kitchen wise! Everything was so clean and comfortable - need to upgrade our home pillows to match! Shared pool was always clean and warm, met so many nice people. Evening dock was awesome for catching small fish with the kids. Location is perfect for all the dining Islamorada has to offer. We can’t wait to go back! Thanks again!
Guest favorite
Villa in Islamorada
4.88 out of 5 average rating, 17 reviews

Islamorada house with best location. Lic # 24-0055

LucaRating, 5 stars3 weeks ago
Very clean and spacious. Great hosts. We did not need them during the stay but all requests were responded to promptly leading up to the stay.
Villa in Key Largo
4.85 out of 5 average rating, 46 reviews

2bd/2ba Ocean Retreat in Kawama Yacht Club

JanetRating, 5 stars1 month ago
A beautiful unit, nice beds and everything as pictured! Paul was good on communication. However, the small community at Kawama is becoming over- crowded. Many times the pools are full and over capacity with screaming kids, and no chairs are available to just sit by the pool. Large parties are happening most every weekend, with a lot of drinking, smoking, and loud music. It’s not Paul’s fault, but the atmosphere here isn’t as quiet and kid friendly as it used to be!
Guest favorite
Villa in Islamorada
4.83 out of 5 average rating, 6 reviews

Isla Mirabelle: Waterfront Pool, Dock, Walkable

JeffryRating, 5 stars2 months ago
The property was better than described. A great quiet getaway. At the same time a lot to do for all. For kids, a playground, park and library adjacent to the property. This is beyond what is available throughout the Keys. Looking forward to our next stay.

Destinations to explore

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