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

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Aug 3 – 10

R4,151 ZAR per night

Guest favorite

Home in Key Colony Beach

4.98 out of 5 average rating, 50 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Aug 24 – 31

R4,930 ZAR per night

Guest favorite

Townhouse in Duck Key

4.98 out of 5 average rating, 141 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

Oct 20 – 27

R8,800 ZAR per night

Guest favorite

Condo in Key Colony Beach

4.96 out of 5 average rating, 171 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Oct 24 – 31

R6,527 ZAR per night

Guest favorite

Boat in Islamorada

4.92 out of 5 average rating, 327 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Jan 28 – Feb 4

R3,571 ZAR per night

Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 82 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

May 25 – Jun 1

R3,685 ZAR per night

Superhost

Villa in Marathon

4.89 out of 5 average rating, 145 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!

Dec 17 – 24

R8,591 ZAR per night

Guest favorite

Home in Marathon

5.0 out of 5 average rating, 10 reviews

Million Dollar View

Take it easy at this unique and tranquil getaway. Enjoy endless open water views from anywhere on this acre-sized, OCEAN FRONT Gulf-side estate. Coconut palms, private hot tub & pool, boat ramp, and a 285 foot long private pier great for catching fish and spectacular sunsets. Like a private resort, you can play giant chess on the beach, win at ping pong, take out a kayak, or paddle board or stroll through fabulous gardens with no staff to tip. License VACA-23-190

Dec 7 – 14

R18,610 ZAR per night

Guest favorite

Home in Marathon

4.97 out of 5 average rating, 32 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

You don't come to the islands to stay in a town! Relax in our tropical paradise beach home away from the traffic and noise of US Hwy #1. The perfect location has now been turned into the perfect oasis. Special features include a gourmet kitchen, private pool surrounded by lush landscaping, private 300' pier/dock with a fish cleaning station. Our guests enjoy luxury bedding with quality linens, fluffy towels and bathrobes. Wireless internet service and cable tv.

Apr 19 – 26

R11,904 ZAR per night

Guest favorite

Home in Marathon

4.96 out of 5 average rating, 124 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Jul 27 – Aug 3

R8,348 ZAR per night

Superhost

Apartment in Marathon

4.86 out of 5 average rating, 94 reviews

Cozy Keys Efficiency 8a

Efficiency has a queen size bed, a 3-seat leather sofa and a small dining table with 2 chairs. Private bathroom. Mini split ductless cooling AC. Kitchen is fully equipped with 4 burner stove, microwave, medium size refrigerator with freezer. Enjoy the breezes on your patio, each unit has a gas BBQ grill and a picnic bench outside. Enjoy a swim in our shared pool. Pricing include 12.5 % tax Efficiency has a 2 person maximum occupancy - no exceptions.

Aug 7 – 14

R3,954 ZAR per night

Superhost

Home in Marathon

4.82 out of 5 average rating, 22 reviews

P58 - Gulf Front Luxury 4 bedroom 4 bath with priv

This beautiful Polynesian style home offers 4 bedrooms, 4 baths, beautifully landscaped grounds and a large, private, heat optional pool. Ideally located on the open water of the Gulf of Mexico. - Maximum Occupancy: 8 guest (includes adults and children of any age) (*children of any age, including infants, count toward occupancy) - Parking: 4 vehicle max - Dock: 50 ft. (*strict 1 boat max.) **Boat lift is NOT available for guest use.

Jan 11 – 18

R15,733 ZAR per night