Resort
10.0(1 Review)
1 Bath
2 Guests
Parking
Pool
Kitchen
Air Conditioner
US $185/Night
7 Nights - US $1,292
Grassy Key Resorts
10.0
Villa
7.6(37 Reviews)
175 Bedrooms
22 Baths
116 Guests
1182.49 ft²
Private Beach
Oceanfront
Hot Tub
Breakfast
US $595/Night
7 Nights - US $4,167
US $679/Night
7 Nights - US $4,750
US $227/Night
7 Nights - US $1,590
Resort
7.1(684 Reviews)
16 Baths
47 Guests
525.28 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Parking
US $202/Night
7 Nights - US $1,416
Resort
7.1(261 Reviews)
40 Baths
161 Guests
818.44 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Breakfast
US $305/Night
7 Nights - US $2,134
Resort
6.9(74 Reviews)
4 Baths
19 Guests
301.38 ft²
- Parking
- Pool
Balcony/Terrace
View
US $187/Night
7 Nights - US $1,311
Hotel
8.8(622 Reviews)
9 Baths
655.06 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $235/Night
7 Nights - US $1,647
Hotel
8.0(376 Reviews)
10 Baths
88.26 ft²
- Oceanfront
- Parking
- Pool
Ocean View
US $231/Night
7 Nights - US $1,620
Condo
10.0(228 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
Private Pool- Oceanfront
- Hot Tub
- Parking
US $431/Night
7 Nights - US $3,020
Villa
10.0(3 Reviews)
2 Bedrooms
3 Baths
6 Guests
904.17 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $373/Night
7 Nights - US $2,614
US $2,231/Night
7 Nights - US $15,619
Why Choose Rent By Owner for your Grassy Key Resorts?
What makes our Resorts special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Grassy Key
How to Book Your Grassy Key Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Resorts Amenities
What amenities can you expect?
Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Grassy Key Resorts Frequently Asked Questions
1. What are the top Resorts in Grassy Key?
There are a lot of options in Grassy Key. If you plan on staying in the Grassy Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Grassy Key:
- Key Lime Kottage- Waterfront Home on Gulf of Mexico w/Private Pool, Dock & More
- Renovated 2BR Villa with Spa, Water Views & Private Patio with Private Dip Pool!
- Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
- ★Remodeled tropical delight townhome★private plunge pool close to fun activities
- Wide Horizon oceanfront. 4 bedroom, 4 ½ bath, kayaks, pool + observation deck.
- Charming 3-bedroom house featuring a heated private pool.
- Private Pool Oasis - Centrally Located in Florida Keys
- Beachy Townhome Perfect for a Warm Getaway!
- MILLION DOLLAR VIEW very private 4 bedroom resort with pool, pier, kayaks, spa
- Waterfront Retreat
2. How many Resorts are available in Grassy Key?
Currently, the total number of properties listed by RBO in 2026 is over 9 in the Grassy Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Grassy Key.
More Rentals You May Like Near Grassy Key
House
10.0(61 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $371/Night
7 Nights - US $2,594
Villa
10.0(1 Review)
2 Bedrooms
3 Baths
6 Guests
904.17 ft²
- Oceanfront
- Parking
Spa- Ocean View
US $387/Night
7 Nights - US $2,710
House
10.0(41 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $375/Night
7 Nights - US $2,624
Villa
10.0(1 Review)
2 Bedrooms
3 Baths
6 Guests
904.17 ft²
- Oceanfront
- Parking
- Spa
- Ocean View
US $378/Night
7 Nights - US $2,646
House
10.0(38 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $581/Night
7 Nights - US $4,064
House
10.0(1 Review)
2 Bedrooms
3 Baths
6 Guests
904.17 ft²
- Parking
- Balcony/Terrace
- View
Internet
US $636/Night
7 Nights - US $4,450
Villa
10.0(25 Reviews)
2 Bedrooms
2 Baths
6 Guests
980 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $458/Night
7 Nights - US $3,205
House
9.6(22 Reviews)
2 Bedrooms
3 Baths
6 Guests
904.17 ft²
- Oceanfront
- Parking
- Spa
- Ocean View
US $669/Night
7 Nights - US $4,684
House
10.0(21 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $376/Night
7 Nights - US $2,635
House
9.6(5 Reviews)
4 Bedrooms
3 Baths
8 Guests
1323.96 ft²
- Balcony/Terrace
- Air Conditioner
Pet Friendly
Child Friendly
US $512/Night
7 Nights - US $3,584
House
10.0(16 Reviews)
1 Bedroom
1 Bath
4 Guests
852 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $331/Night
7 Nights - US $2,314
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $480/Night
7 Nights - US $3,357
