Grassy Key vacation rentals

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Top-rated vacation rentals in Grassy Key

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Camper/RV in Key Largo

4.96 out of 5 average rating, 113 reviews

Paradise Casa Bayfront sunsets,pool,King bed ,dock

Welcome to Paradise Casa! Just five feet from the waterfront, you will think your on a cruise ship when you look out the windows. Breathtaking Unobstructed views of the sunset every night. This Glamping at its finest with an amazing pool. 2 bedrooms plus loft, with the main bedroom having a king size bed. Fireplace, fully stocked kitchen, massage chairs, 2 AC units for your comfort. 2 miles from John Pennekamp that has kayak rentals, glass bottom boats, create memories scuba diving/snorkeling

Superhost

A view of the oceanfront community features modern two-story buildings with white exteriors and metal roofs. Palm trees provide greenery amongst the paved pathways. The blue sky is filled with fluffy clouds, creating a bright and welcoming atmosphere.

Apartment in Marathon

5 out of 5 average rating, 4 reviews

Ocean Side Paradise Awaits!

This gated oceanfront property spans over 7 acres and boasts an Olympic size pool overlooking the mesmerizing Atlantic Ocean. Take advantage of the many tiki huts, fishing dock, air-conditioned clubhouse, and grilling station to cook up your fresh catch. Our turnkey townhouse is perfect for a short vacation or a longer-term stay. Everything in the complex, from the facilities to the furnishings, is brand new. Don't miss the opportunity to experience paradise at its finest. Book your stay now!

Guest favorite

A serene aquatic scene showcases crystal-clear turquoise waters stretching to the horizon. Small boats are seen floating on the surface, with a few partially submerged. Fluffy white clouds drift across a deep blue sky, enhancing the tranquil environment.

Vacation home in Key Largo

4.94 out of 5 average rating, 116 reviews

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

Superhost

A modern living area features a spacious white sectional sofa adorned with blue and green decorative pillows. A wooden dining table with white chairs is positioned nearby. Above, a stylish fan circulates air while artwork in calming hues decorates the walls, complementing the light wood flooring.

Home in Key Largo

4.91 out of 5 average rating, 100 reviews

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach

No hidden fees! Casa Azul blends luxury and laid-back island vibes in the heart of Key Largo. With Superhost status and hundreds of 5-star reviews, a perfect escape. Voted the #1 Vacation Rental in Key Largo, it’s ideal for families, couples, and groups alike. Enjoy a free golf cart, fast Wi-Fi, 2 pools, private beach, saltwater lagoon, kayaks, tennis and pickleball courts with gear, marina access, boat ramp, trailer parking, and optional slip rentals. Salt Life meets luxury - this is the one.

Superhost

A serene waterfront scene is depicted, featuring a calm body of water reflecting the soft hues of dusk. A thatched-roof structure and a boat are aligned along the shore, surrounded by lush greenery and rocky formations.

Camper/RV in Key Largo

4.92 out of 5 average rating, 26 reviews

146 RV Vacation Rental n Key Largo Kampground, FL

RV has Kitchen with new stove/oven, kitchen utensils, Keurig coffee maker, rice cooker, toaster, etc. Sleeps 4 adults or 2 adults and 3 kids comfortably. Bed sheets and bath/pool towels provided. Just bring personal necessities. One bathroom/One bedroom with closet dresser and bunkbeds. Futon in living area and dining table. 2 TV's with cable. Large deck outside furnished with BBQ grill and mini refrigerator for your comfort. There's an adult heated pool/kiddie pool and a kids playground.

Guest favorite

A serene waterway is framed by lush greenery, with the calm surface reflecting the surrounding trees and structures. Boats are docked at a well-maintained pier, with the gentle morning light casting a warm glow on the scene.

Apartment in Key Largo

4.93 out of 5 average rating, 154 reviews

2/1 Oceanfront Apartment with Dockage

The Seaside Vista is a luxurious ocean front retreat located in Key Largo. Only 1 hour from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From great dining, to water sports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled , enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer. MC Permit #: 21302180

Guest favorite

Condo in Tavernier

4.99 out of 5 average rating, 106 reviews

Modern and Coastal Ocean Pointe 2307

Are you looking for a Caribbean Vacation in a tropical resort without leaving the USA? Look no further than our Ocean view 2 bedroom and 2 bath condo at Ocean Pointe Suites! Our property offers: 24 hour front gate security, Heated Junior Olympic Pool with 15 person hot tub, tropical Beach, Marina, Tennis/Pickle ball courts. Enjoy our newly re opened ISLAND GRILL pool bar! We are located 60 miles from Miami International Airport and 90 miles from Fort Lauderdale International Airport.

Guest favorite

A heated pool is framed by two thatched umbrellas, offering shade and relaxation. Surrounding the pool are several wooden lounge chairs, inviting comfort in the sun. Lush greenery is visible in the background, enhancing the serene ambiance of the outdoor space.

Home in Marathon

5 out of 5 average rating, 33 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Superhost

Townhouse in Key Largo

4.84 out of 5 average rating, 69 reviews

VOTED TRIPADVISOR'S #1 DESTINATION, POOL, TENNIS

4 PROFESSIONALLY DECORATED MODELS TO CHOOSE. CLICK ON MY PROFILE TO SEE ALL MY LISTINGS. BOAT SLIP AVAILABLE AT ADDITIONAL COST, FAST WIFI. KID'S KAYAKS WITH LIFE JACKETS, TENNIS, LAGOON DIRECTLY OUTSIDE THE BALCONY AND 2 POOLS. This is a High living 2/2 LICENSED VACATION RENTAL PROPERTY is a luxury townhouse you would not expect to find in the Florida Keys. With it's Malibu feel, this Nautical Chic two Bedroom unit is located at The Kawama Yacht Club on MM 99

Superhost

A relaxing outdoor seating area is surrounded by vibrant blue chairs facing a calm waterway. A central table features a fire pit, and string lights hang above. Lush greenery can be seen along the shoreline, creating a tranquil atmosphere.

Camper/RV in Key Largo

4.78 out of 5 average rating, 18 reviews

A motorhome in paradise

This place is truly unique. Beautiful cozy has everything you need to have a good vacation pool Marine park Rest area By the sea beautiful views of the sunfall Area to wash up near supermarkets and restaurants definitely a beautiful place It is a TRAILER FIELD surrounded by nature it is not a 5-star hotel or anything like it If you really like adventure and feeling nature air sea beautiful views this is a perfect place No pet

Superhost

Home in Marathon

5 out of 5 average rating, 5 reviews

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort featuring 13 luxury vacation homes, 74 private marina slips and a centrally located pool deck and clubhouse. We provide unparalleled service in an intimate setting allowing you to relax and unwind. We are located in Marathon in The Middle Keys, so you can easily explore all that The Keys have to offer.

Superhost

Townhouse in Key Largo

4.82 out of 5 average rating, 110 reviews

Oceanfront Resort W/Indoor Pickleball - Spacious!

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.

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What guests are saying

Catch n' Relax Canalfront Cottage in Marathon

4.97 out of 5 average rating, 32 reviews1 month ago

We stayed for 11 nights at Wendy's beautiful home. We had everything we needed for our entire stay. The area is very quiet and peaceful. It was so lovely walking up on the water and enjoying breakfast outside. Extra touches like having bikes and kayaks to use were also sooo nice! Wendy was very helpful with local spots to check out as well. We will definitely be back!

Cottage in Marathon

What guests are saying

Waterfront Oasis3/2 Direct Ocean

5 out of 5 average rating, 3 reviews9 months ago

Beautiful views and great spaces! We’ve stayed in Marathon several times in different canal houses with our family of 7, and this property is now our new favorite. We couldn’t get enough of all the beautiful views from sunrise to sunset whether it was on the porch, in the pool, or out by the Tiki Hut. Every bedroom has water views as well. Boat access was an easy out to snorkeling, diving, fishing, or whatever you like to do. There are two kayaks for use, which made for some nice outings to explore the immediate area. The kitchen had everything needed for cooking, and even had an extra under-the-counter ice machine. We had a great time here, and would stay again. Thank you to the owners for sharing your property.

Home in Marathon

What guests are saying

Amazing Bayfront New House with Dock and Pool!

5 out of 5 average rating, 34 reviews1 month ago

We had a great stay. The highlights were the view of the bay and the heated pool. The beds were comfortable and the open space was great to gather as a family. Unfortunately we didn’t catch too many fish but had a great time trying. The paddle boards were perfect for our teenage kids. Would definitely love to return.

Home in Marathon

What guests are saying

Boaters delight! 1 min to open water, Dock & Beach

4.89 out of 5 average rating, 18 reviews2 months ago

Wonderful home on canal that opens up to gulf. The home had everything that was described and was comfortable with AC. Cannot think of anything we needed that was not there. Terrific views from balcony. Saw lots of wildlife including manatees and the iguanas were fun to watch. There was a double and a single kayak to use as well as bikes to get around as the traffic was busy. There are close neighbors next door but they were quiet. If you want a place to relax, this fits the bill.

Home in Marathon

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