Outdoor Places - Vacation Rentals in Grassy Key

Marathon Waterfront Recreational Paradise From US $679
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
Grassy Flats Resort & Beach Club From US $231
         

9.4 (345 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Grassy Key

Over 491+ Luxury Places to Stay in or Near Grassy Key

Top-Rated Vacation Rentals with a Pool in Grassy Key

Over 323+ Top-Rated Vacation Rentals with a Pool in or Near Grassy Key

Pet-Friendly Vacation Rentals in Grassy Key

Over 91+ Pet-Friendly Vacation Rentals in or Near Grassy Key
Sea and Sky From US $348
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Gulf View Waterfront Resort From US $113
         

8.6 (522 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautiful Waterfront Gulf of America Great location. From US $721
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Paradise Found From US $483
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Grassy Key

Over 112+ Large Vacation Homes & Villas in or Near Grassy Key
Seas the Keys Getaway From US $279
         

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8.8 (6 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Waterfront Duck Key Villa From US $1,051
         

9.2 (61 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV
Hawks Cay Island Retreat - Duck Key - Pool & Patio From US $532
         

10.0 (6 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA From US $491
         

Florida Keys 3BR w/Perks – No Hidden Fees From US $1,123
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Florida Keys 3BR 1Lvl Villa w/No Hidden Fees From US $1,108
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Grassy Key

Over 171+ Wheelchair Accessible Vacation Homes in or Near Grassy Key
FL Keys 2BR 2Lvl | Nr Spa+KidsClb | No Hidden Fees From US $1,095
         

Harbor Hideaway Villa 7066 From US $512
         

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9.6 (5 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Hawks Cay Resort From US $431
         

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8.0 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Florida Keys 2BR Villa w/Balcony | No Hidden Fees From US $943
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Florida Keys 2BR Villa w/Porch | No Hidden Fees From US $933
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Florida Keys | 2BR Stay – No Hidden Fees From US $1,002
         

9.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Grassy Key Varoom and Airbnb Places to Stay Under $200

Over 17+ Grassy Key Varoom and Airbnb Places to Stay Under $200
Oceanfront and Sunrise Views! From US $150
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Harbor Villa From US $196
         

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9.5 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Rainbow Bend Resort From US $145
         

8.2 (769 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • TV
Viamarhe Cabin-Private beach, Kayak, yard games From US $165
         

8.8 (15 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Authentic And Charming Little Cottage 60 Ft From The Ocean From US $103
         

Duck Key Vacation Rental w/ Boat Launch Access From US $120
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Your Own Home Steps From The Ocean From US $129
         

9.2 (10 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Grassy Key

Over 309+ Instantly Bookable Vacation Homes in or Near Grassy Key
Waterfront Retreat From US $516
         

10.0 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Waterfront Island Escape with Private Plunge Pool From US $601
         

10.0 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Beachy Townhome Perfect for a Warm Fall Getaway! From US $575
         

10.0 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Beautiful Ocean Front View From US $966
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Tiny Villa, Big Ocean Views| Breathtaking Sunsets From US $659
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Grassy Key Vacation Rentals

With more than 500 Grassy Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Outdoorplaces and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Grassy Key.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Outdoorplaces Grassy Key, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Grassy Key. Places to stay near Grassy Key are 712.38 ft² on average, with prices averaging $943 a night.

Outdoorplaces makes it easy and safe to find and compare vacation rentals in Grassy Key with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Grassy Key

Type Count
Vacation Homes 314
Holiday Apartments 60
Villas 59
Hotels with Suites 39
Resorts 7
Cottages 4
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Grassy Key

Pro Tip: Outdoorplaces makes it easy to compare the best listings on Outdoorplaces homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Outdoorplaces homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Grassy Key.

Weather in Grassy Key

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