Grassy Key Rentals

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97 Houses

Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL

Grassy Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Wireless Internet

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Price per night from

$567

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

Match: Wireless Internet

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Price per night from

$252

Responds fast! avg. 1 hour 39 minutes

Match: Wireless Internet

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Price per night from

$801

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

Match: Wireless Internet

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Price per night from

$252

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Wireless Internet

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Price per night from

$229

Great rentals within 20 miles that match your search

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

Match: Wireless Internet

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Price per night from

$673

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wireless Internet

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Price per night from

$687

Paradise with or without a boat Clean Waterfront Beach Near Pet free

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 51 minutes

Match: Wireless Internet

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Price per night from

$343

Duck Key 50% off October

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Wireless Internet

All filters match

Price per night from

$658

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Wireless Internet

All filters match

Price per night from

$1,028

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$286

Match: Wireless Internet

All filters match

Price per night from

$1,087

Large Home near Beach & Key West

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Wireless Internet

All filters match

Price per night from

$445

Match: Wireless Internet

All filters match

Price per night from

$1,316

Last Minute Sunday to Sunday Availability August 22nd - August 29th

Marathon Shores house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$515

Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$239

Private studio with dock. Perfect getaway for fishing and grilling.

Marathon Shores studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Wireless Internet

All filters match

Price per night from

$172

Oceanside, Pet Friendly, Smart Home with-SUP, kayak with and 60 ft Dock

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Wireless Internet

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Price per night from

$258

Match: Wireless Internet

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Price per night from

$332

3Bd/2Ba POOL on Canal, Dock, Kayaks, Bikes, Fishing Poles, Sombrero Beach 2.3mi

Marathon Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$572

"Gulfside Grouper", Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Wireless Internet

All filters match

Price per night from

$980

Oceanside waterfront 2/2 home with 55ft dock and paddle equipment

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$286

Key Colony Beach Oasis

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Wireless Internet

All filters match

Price per night from

$1,144

The Mini Coconut

Marathon Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 54 minutes

Match: Wireless Internet

All filters match

Price per night from

$258

Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$307

2-Story condo w/ panoramic views and balconies

Marathon condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$373

Hidden Gem Sunset Views-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$983

Big Pine Key/Hot tub/Canal Home/updated

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Wireless Internet

All filters match

Price per night from

$228

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$264

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$327

New Listing! Gone Coastal-Waterfront Bring Your Boat! Cabana Club Membership

Key Colony Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Wireless Internet

All filters match

Price per night from

$217

Villa Bella 3/3 with Private Pool and Dock

Key Colony Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Wireless Internet

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Price per night from

$413

Match: Wireless Internet

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Price per night from

$819

Beautiful Beachfront Home w/Heated Pool+45' Dock

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

“Beautiful Home and Beautiful Beach Across the Street” My family had a fabulous relaxing vacation. The house and amenities were great. We had a beautiful front porch to watch the morning sunrise and beautiful views of Sombrero Beach. The guys enjoyed fishing everyday while the ladies enjoyed the beach. The beach opens at sunrise and closes at sunset. We had great weather and can't wait to return!

Match: Wireless Internet

All filters match

Price per night from

$801

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$602

Pet Friendly Half-Duplex, Cottage with 40' Slip Option at The Boat House Marina

Marathon Shores cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Wireless Internet

All filters match

Price per night from

$195

Thirty Three by The Sea - Vacation Rental Key Colony Beach, FL

Key Colony Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Wireless Internet

All filters match

Price per night from

$344

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Wireless Internet

All filters match

Price per night from

$1,266

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rentals in Grassy Key

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