Grassy Key Rentals

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111 Houses

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

Grassy Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$569

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

Price per night from

$252

Responds fast! avg. 1 hour 39 minutes

Price per night from

$808

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

Price per night from

$252

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$229

Glamping in the Florida Keys

Grassy Key caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$185

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

Price per night from

$679

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

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$693

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$266

Duck Key 50% off October

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$664

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

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$989

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,038

Price per night from

$335

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$329

Price per night from

$1,097

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

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$260

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

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$242

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

Marathon Shores studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$173

2-Story condo w/ panoramic views and balconies

Marathon condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$375

Price per night from

$1,327

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

Marathon Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$577

Key Colony Beach Oasis

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,154

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

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$289

Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool

Marathon Shores house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$749

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

Price per night from

$347

The Butterfly Cottage

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$253

The Mini Coconut

Marathon Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 48 minutes

Price per night from

$260

Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$345

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

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$310

Big Pine Key/Hot tub/Canal Home/updated

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$229

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

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$288

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

Marathon Shores house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$518

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!

Price per night from

$804

Oasis Canal-Front Home: Pool, 30ft Dock, BBQ, and more!

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$518

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

Marathon Shores cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$196

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

Key Colony Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$345

Immaculate Waterfront ~ 2 BR ~ Private Pool, Tiki on Canal! 2 Min Walk to Beach!

Key Colony Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$344

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$604

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rentals in Grassy Key

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