Grassy Key Rentals

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108 Houses

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

Grassy Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$567

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

Price per night from

$252

Responds fast! avg. 52 minutes

Price per night from

$802

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

$184

Great rentals within 20 miles that match your search

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$153

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$140

Island Time 2 (half of duplex)

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$147

Island Time (both halves of duplex)

Big Pine Key house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$235

Our Island Thing

Big Pine Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$277

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$267

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$2,045

2 BEDROOM 2 1/2 BATH VILLA WITH PRIVATE PATIO AND PLUNGE POOL

Duck Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$338

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 3 hours 39 minutes

Price per night from

$114

8c, Efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$229

Florida Keys Beach Home Pool Fishing Diving

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$2,290

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

$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. 1 hour 38 minutes

Price per night from

$344

Duck Key 50% off October

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$659

Price per night from

$332

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

$674

Breezy Palms

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$572

Price per night from

$1,088

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

$240

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

Marathon Shores studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$172

2-Story condo w/ panoramic views and balconies

Marathon condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$373

Price per night from

$1,317

the private and secluded PENINSULARHOUSE

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Nice get away” Beautiful and relaxing. Did alot of snorkeling right off the deck. Enjoyed the paddle boats and the kayaks. When we make it down that way again I would definitely stay here.

Price per night from

$300

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

$573

Key Colony Beach Oasis

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,145

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

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$287

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,030

The Mini Coconut

Marathon Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 48 minutes

Price per night from

$258

Big Pine Key/Hot tub/Canal Home/updated

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$228

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

$343

"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

$982

Family Friendly w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$655

Viewing 38 of 108
rentals in Grassy Key

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