Grassy Key Vacation Rentals & Ski-in/Ski-out Homes
Condo
10.0Exceptional
(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
10.0Exceptional
(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
House
1 Bedroom
1 Bath
- Parking
Pool- Ocean View
- Balcony/Terrace
US $2,231/Night
7 Nights - US $15,619
House
10.0Exceptional
(61 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $385/Night
7 Nights - US $2,698
Villa
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
904.17 ft²
- Parking
Spa- Balcony/Terrace
View
US $387/Night
7 Nights - US $2,710
House
10.0Exceptional
(41 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $379/Night
7 Nights - US $2,650
House
10.0Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $373/Night
7 Nights - US $2,609
Villa
10.0Exceptional
(25 Reviews)
2 Bedrooms
2 Baths
6 Guests
980 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $433/Night
7 Nights - US $3,029
House
10.0Exceptional
(21 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $348/Night
7 Nights - US $2,433
Luxury Places to Stay in Grassy Key
Over 560+ Luxury Places to Stay in or Near Grassy Key
Apartment
4 Bedrooms
1 Bath
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
Unlock the Best Price
Apartment
2 Bedrooms
1 Bath
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
Unlock the Best Price
House
9.8Exceptional
(29 Reviews)
4 Bedrooms
3 Baths
8 Guests
1900 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $6,298/Night
7 Nights - US $44,083
Apartment
2 Bedrooms
1 Bath
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $3,973/Night
7 Nights - US $27,812
House
10.0Exceptional
(8 Reviews)
9 Bedrooms
8 Baths
24 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,560/Night
7 Nights - US $17,921
Villa
9.8Exceptional
(105 Reviews)
8 Bedrooms
5 Baths
20 Guests
6000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,995/Night
7 Nights - US $13,963
House
10.0Exceptional
(24 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,783/Night
7 Nights - US $12,480
House
10.0Exceptional
(8 Reviews)
5 Bedrooms
4 Baths
12 Guests
6000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,763/Night
7 Nights - US $12,339
House
5 Bedrooms
4 Baths
12 Guests
3100 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,642/Night
7 Nights - US $11,494
Top-Rated Vacation Rentals with a Pool in Grassy Key
Over 362+ Top-Rated Vacation Rentals with a Pool in or Near Grassy Key
House
10.0Exceptional
(277 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $534/Night
7 Nights - US $3,737
House
10.0Exceptional
(166 Reviews)
4 Bedrooms
3 Baths
10 Guests
1320 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,129/Night
7 Nights - US $7,902
House
10.0Exceptional
(48 Reviews)
4 Bedrooms
4 Baths
8 Guests
2260 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $856/Night
7 Nights - US $5,993
House
10.0Exceptional
(44 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $820/Night
7 Nights - US $5,742
House
10.0Exceptional
(43 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $529/Night
7 Nights - US $3,706
House
10.0Exceptional
(38 Reviews)
4 Bedrooms
3 Baths
8 Guests
1867 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $769/Night
7 Nights - US $5,381
House
10.0Exceptional
(16 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $333/Night
7 Nights - US $2,332
House
10.0Exceptional
(13 Reviews)
4 Bedrooms
4 Baths
8 Guests
3400 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $623/Night
7 Nights - US $4,362
House
10.0Exceptional
(10 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $529/Night
7 Nights - US $3,701
Pet-Friendly Vacation Rentals in Grassy Key
Over 104+ Pet-Friendly Vacation Rentals in or Near Grassy Key
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
Kitchen
Air Conditioner
Internet
US $647/Night
7 Nights - US $4,532
House
10.0Exceptional
(1 Review)
2 Bedrooms
3 Baths
6 Guests
904.17 ft²
- Parking
- Balcony/Terrace
- View
- Internet
US $636/Night
7 Nights - US $4,450
Hotel
9.4Exceptional
(501 Reviews)
1 Bath
- Hot Tub
Breakfast- Parking
- Pool
US $267/Night
7 Nights - US $1,868
Cottage
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
3 Guests
600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $378/Night
7 Nights - US $2,645
House
9.6Exceptional
(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
Villa
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
904 ft²
- Oceanfront
- Parking
- Spa
- Ocean View
US $426/Night
7 Nights - US $2,979
House
9.8Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $446/Night
7 Nights - US $3,125
Villa
9.6Exceptional
(85 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $452/Night
7 Nights - US $3,165
House
9.6Exceptional
(70 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $286/Night
7 Nights - US $2,005
Large Vacation Homes & Villas in Grassy Key
Over 136+ Large Vacation Homes & Villas in or Near Grassy Key
Villa
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $480/Night
7 Nights - US $3,357
Villa
10.0Exceptional
(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
5 Bedrooms
3 Baths
12 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $714/Night
7 Nights - US $4,995
Villa
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $473/Night
7 Nights - US $3,311
Villa
9.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Pool
- Spa
- Balcony/Terrace
- Air Conditioner
US $338/Night
7 Nights - US $2,366
Villa
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $524/Night
7 Nights - US $3,667
Villa
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $649/Night
7 Nights - US $4,543
Villa
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $563/Night
7 Nights - US $3,941
Villa
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $563/Night
7 Nights - US $3,941
Wheelchair Accessible Vacation Homes in Grassy Key
Over 196+ Wheelchair Accessible Vacation Homes in or Near Grassy Key
Villa
7.0Very Good
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $499/Night
7 Nights - US $3,490
House
8.1Excellent
(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
785.77 ft²
- Spa
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $334/Night
7 Nights - US $2,341
Hotel
8.2Excellent
(1006 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $303/Night
7 Nights - US $2,120
Hotel
10.0Exceptional
(2 Reviews)
1 Bath
- Hot Tub
- Parking
- Pool
- Spa
US $408/Night
7 Nights - US $2,856
Villa
7.6Very Good
(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
Hotel
10.0Exceptional
(1 Review)
1 Bath
- Hot Tub
- Parking
- Pool
- Spa
US $361/Night
7 Nights - US $2,524
Hotel
8.0Excellent
(1 Review)
1 Bath
- Hot Tub
- Parking
- Pool
- Spa
US $535/Night
7 Nights - US $3,743
Hotel
8.0Excellent
(1 Review)
1 Bath
- Hot Tub
- Parking
- Pool
- Spa
US $436/Night
7 Nights - US $3,050
New
Hotel
6.0Good
(1 Review)
1 Bath
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $444/Night
7 Nights - US $3,106
Grassy Key Resorts and Airbnb Homes Under $200
Over 21+ Grassy Key Resorts and Airbnb Homes Under $200
Condo
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
510 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $150/Night
7 Nights - US $1,048
Resort
6.9Good
(74 Reviews)
4 Baths
19 Guests
301.38 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $187/Night
7 Nights - US $1,311
Hotel
8.4Excellent
(631 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- View
US $141/Night
7 Nights - US $985
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $195/Night
7 Nights - US $1,362
Apartment
1 Bedroom
1 Bath
4 Guests
505.9 ft²
- Parking
- Internet
- Child Friendly
Wheelchair Accessible
US $130/Night
7 Nights - US $910
House
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
6 Guests
1010 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $187/Night
7 Nights - US $1,306
Condo
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Child Friendly
Bedding/Linens
US $93/Night
7 Nights - US $649
House
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $178/Night
7 Nights - US $1,249
Condo
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
510 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $120/Night
7 Nights - US $840
Instantly Bookable Vacation Homes in Grassy Key
Over 381+ Instantly Bookable Vacation Homes in or Near Grassy Key
House
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
852 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $325/Night
7 Nights - US $2,272
House
1 Bedroom
1 Bath
2 Guests
- Child Friendly
Security/Safety
US $551/Night
7 Nights - US $3,856
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
780 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $443/Night
7 Nights - US $3,102
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $439/Night
7 Nights - US $3,070
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $433/Night
7 Nights - US $3,032
Villa
9.8Exceptional
(195 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $491/Night
7 Nights - US $3,437
Villa
9.8Exceptional
(185 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $491/Night
7 Nights - US $3,437
House
9.8Exceptional
(137 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $749/Night
7 Nights - US $5,244
Apartment
9.8Exceptional
(98 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $249/Night
7 Nights - US $1,742
Book a Last Minute Place to Stay in Grassy Key
About Grassy Key Vacation Rentals
Explore over 569 vacation rentals in Grassy Key with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Grassy Key for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Grassy Key. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Grassy Key tailored to your preferences. On average, these rentals offer 682.24 ft² of space, and are priced at an average of US $1,001 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Grassy Key at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Grassy Key
| Type | Count |
|---|---|
| Vacation Homes | 351 |
| Villas | 68 |
| Holiday Apartments | 44 |
| Cottages | 4 |
| Cabin Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Grassy Key
★ Pro Tip: Discover Your Ideal Vacation Rental in Grassy Key with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Grassy Key, FL
View the weather forecast for Grassy Key before booking your Grassy Key Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Grassy Key, FL
Sunski offers a large selection of top attractions around Grassy Key . Research things to do on your vacation before you visit Grassy Key.
Frequently Asked Questions About Grassy Key?
What are the top vacation rentals in Grassy Key?
When organizing your trip to Grassy Key, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Grassy Key. Peruse our collection of highly-rated properties and secure your reservation today.
- 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
How many vacation rentals have private pools in Grassy Key?
Uncover 123 vacation rentals boasting private pools near Grassy Key. Explore top-rated RBO homes offering access to a swimming pool:
- Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
- Seas the Keys Getaway with plunge pool/spa
- Isabella on Paradise Place 2 bed 2 bath with Exotic Magnificent pool and Open water views 200 ft of dockage
- Manatee Bay | Private Dip Pool, Water Views & Tropical Duck Key Escape
Which vacation homes or resorts in Grassy Key are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Grassy Key. Enjoy great views, locations and save money with SunSki Resorts.™
- Cozy 2-bedroom mobile home in enchanting Marathon with WiFi, AC.
- Beach House Getaway - Waterfront Villa in Duck Key
- Rainbow Bend Resort
How many SunSkiResorts vacation rentals or resorts are available in Grassy Key?
Discover the ideal vacation rental in Grassy Key with SunSki Resorts™. We provide an extensive selection of over 569 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Grassy Key.
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