Villa vacation rentals in Grassy Key

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Top-rated villa rentals in Grassy Key

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Guest favorite

Villa in Duck Key

4.98 out of 5 average rating, 59 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.

Aug 29 – Sep 5

$311 per night

Guest favorite

Villa in Marathon

4.95 out of 5 average rating, 119 reviews

4/3 Private Pool w Heater/Dock/Kayaks & more incl.

Our home is close to grocery stores, restaurants and dining, the beach, family-friendly activities, and public transport. You’ll love my place because of the high ceilings, the views, the location, the people, and the ambiance. Our place is good for couples, business travelers, and families (with kids). Included in the rental you'll have access to 4 bicycles for adults and 2 tandem kayaks and 2 paddle boards during your stay. We have a cooler, 2 beach umbrellas and 4 beach chairs for your use.

Feb 15 – 22

$768 per night

Guest favorite

Villa in Duck Key

4.86 out of 5 average rating, 21 reviews

Family Friendly Sunset Oasis!

Welcome to Driftwood Villa.This newly renovated 2 bed 1.5 bath luxury villa is located in the popular area duck key alongside of Hawks Cay Resort.Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including small kitchen appliances , silverware ,plates , cups , and pots. Linens and towels are also provided THIS PROPERTY DOES NOT HAVE ACCESS TO HAWKS CAY AMENITIES

Aug 17 – 24

$315 per night

Guest favorite

Villa in Key Largo

4.96 out of 5 average rating, 52 reviews

Marina-Ocean view, New Kitchen, Lagoon 3/3 2100sf

Licensed! You have just discovered one of the most unique properties in the heart of Key Largo. This Ocean Front Villa is located in a safe gated community. Your family will love the panoramic view from this spacious and luxurious Villa. This two-story, 3 bedroom, 3 bath Villa and 2 Family Rooms with a Brand New Kitchen overlooks the Marina and the Atlantic Ocean! Inside you’ll find tasteful furnishings with TV in each room, free Wi-Fi and the COLDEST A/C to cool down after a hot Florida day

Mar 18 – 25

$555 per night

Superhost

Villa in Marathon

4.78 out of 5 average rating, 67 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.

Oct 24 – 31

$245 per night

Guest favorite

Villa in Key Colony Beach

5.0 out of 5 average rating, 13 reviews

Keys Hideaway Completely Remodeled w/ Cabana Club

Completely remodeled, clean 2/2 villa with 40ft dock - bring your boat up to 50ft. Great view of both the canal and causeway from your back yard. Directly across the street are the following amenities: 9-Hole Golf Course Pickleball Tennis Basketball Children’s Playground Horseshoe Bocce Ball Walk to the beach, pool and Tiki bar at the Cabana Club (membership included with the rental). You can either relax and grill on the back patio and/or walk to a local restaurant/bar on the waterfront.

Oct 13 – 20

$235 per night

Guest favorite

Villa in Marathon

5.0 out of 5 average rating, 9 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.

Jan 30 – Feb 6

$579 per night

Guest favorite

Villa in Key Largo

4.92 out of 5 average rating, 100 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.

Nov 10 – 17

$437 per night

Superhost

Villa in Islamorada

4.89 out of 5 average rating, 9 reviews

Beachfront Paradise | by The Glam Homes

This is a truly unique and spectacular Villa thanks to its breathtaking view of the sea and its warm sandy beach. On the stunning beach you will find paddle boards and kayaks (both for rent) and comfortable sun loungers while you sunbathe and enjoy the dreamy sunsets. Get ready for a private saltwater pool with lush tropical landscaping plus a cozy cabana with a dining table, a cinema (projector) and a lovely fire pit! The interior has 4 bedrooms, 4 bathrooms and much more!

Oct 18 – 25

$830 per night

Superhost

Villa in Marathon

4.89 out of 5 average rating, 148 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!

Apr 10 – 17

$384 per night

Guest favorite

Villa in Marathon

5.0 out of 5 average rating, 19 reviews

Sombrero Beach house with dock and tropical pool

Casa MarBella @ Sombrero Beach offers plenty of indoor and outdoor space. Enjoy our beautiful pool with flowing waterfall which can be heated for an additional fee. Please inquire before booking. Dock on deep water canal with shore power and commercial ice maker in the garage. Weber gas grill, convenient outdoor counter with built-in ice chest and sink. Large yeti cooler with wheels, paddle board, 12ft fishing kayak, beach tricycle, pedal boat and 4 bikes.

Dec 6 – 13

$825 per night

Guest favorite

Villa in Duck Key

5.0 out of 5 average rating, 49 reviews

Duck Key *Bliss* Private Pool & Patio

Enjoy a great family vacation in this comfortable cozy home located in The Sanctuary, an exclusive gated area of Hawks Cay Resort. This home offers a private swimming pool and patio in a lush tropical setting, large Smart 4K TV's, high speed internet - 1,000 mbps, and fully equipped kitchen. Close to great restaurants and fun tropical activities. Relax, unwind, bond, and make new memories at the Florida Keys.

Sep 22 – 29

$534 per night