Grassy Key Vacation Home Rentals, Treehouses & more


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Areas near Grassy Key

1 / 16

Villa Pamela - Tropical Paradise

  • 3
  • 8
  • 7 nights min

$429

Details

Great rentals within 20 miles that match your search

1 / 49

Oceanfront estate w/ private beach access, pool w/swim-up bar, hot tub, rec room

  • 6
  • 14
  • 28 nights min

$580

Details

1 / 21

P43~Fisherman's Retreat Marathon ~ Manor Lane 3 bedroom 3 bath

  • 3
  • 8
  • 7 nights min

$250

Details

1 / 47

Dog-friendly family home on deepwater canal, close to beaches!

  • 3
  • 8
  • 7 nights min

$119

Details

1 / 24

Lovely bayfront home overlooking Lake Lucille with a dock

  • 3
  • 6
  • Min stay varies

$120

Details

1 / 29

Dog-friendly, oceanfront home w/ private pool, hot tub, & private beach

  • 4
  • 10
  • 7 nights min

$644

Details

1 / 27

Oceanfront escape, w/ million-dollar views & direct beach access

  • 2
  • 6
  • Min stay varies

$99

Details

1 / 25

Dog-friendly bayfront home w/ 35-ft dock, ocean views & great fishing!

  • 2
  • 6
  • 7 nights min

$114

Details

1 / 24

Waterfront home w/ 28ft. dock, shared pool & beach access!

  • 2
  • 4
  • 7 nights min

$136

Details

1 / 28

Florida Keys, Private Fishing Compound, Dock and boat Basin in the Florida Bay

  • 3
  • 6
  • 7 nights min

$243

Details

1 / 38

Waterfront home w/30ft dock, a private beach & shared pool at Cabana Club!

  • 3
  • 6
  • 7 nights min

$192

Details

1 / 34

P21 3 bdm Mediterranean Getaway

  • 3
  • 8
  • 7 nights min

$222

Details

1 / 24

Waterfront 2BR w/ 2 Balconies, 2 Docks, 7 Bikes - Near Bars & Restaurants

  • 2
  • 6
  • 7 nights min

$149

Details

1 / 49

Mockingbird Pointe - Waterfront Tropical Escape

  • 2
  • 6
  • Min stay varies

$254

Details

1 / 24

Stylish, oceanfront condo w/ ocean views & dock - pool & hot tub coming soon!

  • 1
  • 2
  • 28 nights min

$68

Details

1 / 16

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

  • Studio
  • 2
  • 30 nights min

$100

Details

1 / 13

P17 Cozy Canal Front

  • 3
  • 6
  • 7 nights min

$177

Details

1 / 203

Canal, pool, 2 bedrooms and a great breezeway! Key Colony Beach, Florida Keys

  • 2
  • 8
  • 7 nights min

$258

Details

1 / 11

Conch Key TreeTop one BR Cottage with 23' Sailboat

  • 1
  • 4
  • Min stay varies

$150

Details

1 / 20

Royal Palm House

  • 2
  • 6
  • 7 nights min

$157

Details

1 / 16

Tropical Keys Home - Gulf View, 40' Dock, Kayak

  • 2
  • 6
  • 7 nights min

$157

Details

1 / 34

Sandy Beach, Direct Ocean, Pool, Dock & Lagoon

  • 5
  • 14
  • 7 nights min

$1296

Details

1 / 99

AVAIL: July 31-Aug.11 $1800 wk! NEW 30'Dock,65'pool+2 Beaches, sleeps 6 +2 dogs

  • 2
  • 6
  • Min stay varies

$144

Details

1 / 18

4 ROOM LUXURY HOUSE

  • 4
  • 8
  • 7 nights min

$711

Details

1 / 31

P24 Key Colony Bungalow

  • 3
  • 6
  • 7 nights min

$150

Details

1 / 21

4 BR shore home w pool AND Private Island and Boat

  • 4
  • 18
  • 7 nights min

$800

Details

1 / 45

The Manatee Bay ~ Executive Living Waterfront/Pool/Dockage $4,600 Wkly

  • 5
  • 12
  • 7 nights min

$659

Details

1 / 42

Gulf View Suites w/Docks, Pools, Kayaks -Sleeps 20

  • 8
  • 20
  • 7 nights min

$542

Details

1 / 32

Price slashed Oct. 14-Dec. 8, 2017 (excluding Thanksgiving Week) 50% off

  • 3
  • 8
  • 7 nights min

$157

Details

1 / 17

P85 ~ Smooth Sailing - Tropical Single Family, pool home

  • 2
  • 6
  • 7 nights min

$214

Details

1 / 46

Sip your coffee looking out to a tropical sunrise

  • 4
  • 10
  • 7 nights min

$600

Details

1 / 50

my house ~ RA66019 Copa D'oro

  • 3
  • 8
  • Min stay varies

$486

Details

1 / 94

KEYS OCEANFRONT HOME PRIVATE BEACH POOL + 3 VILLAS - YOUR OWN PRIVATE RESORT!

  • 6
  • 18
  • 3 nights min

$490

Details

1 / 24
1 / 24

Studio located 50 yards from ocean, Unit 10

  • 2
  • 5 nights min

$130

Details

1 / 32

Studio located 50 yards from ocean, Unit 9

  • 2
  • 5 nights min

$130

Details

1 / 17

P58 Grassy Key Delight--- 4 Bedroom With Pool

  • 4
  • 8
  • 7 nights min

$429

Details

1 / 26

Efficiency located 50 yards from Ocean, 8a

  • Studio
  • 2
  • 5 nights min

$120

Details

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