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Grassy Key Holiday Rentals

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56 rentals in Grassy Key.
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Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK &  POOL, holiday rental in Grassy Key

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

4 bedrooms
3 bathrooms
Sleeps 10
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Unit 9, Furnished Studio located 50 yards from ocean, holiday rental in Grassy Key

Unit 9, Furnished Studio located 50 yards from ocean

0 bedrooms
1 bathroom
Sleeps 2
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Sunset Catch- Gulf Front Home Incredible Views Pool Dock private and spacious, holiday rental in Grassy Key

Sunset Catch- Gulf Front Home Incredible Views Pool Dock private and spacious

3 bedrooms
2 bathrooms
Sleeps 8
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Unit 10, Furnished Studio located 50 yards from ocean, holiday rental in Grassy Key

Unit 10, Furnished Studio located 50 yards from ocean

0 bedrooms
1 bathroom
Sleeps 2
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Glamping in the Florida Keys, holiday rental in Grassy Key

Glamping in the Florida Keys

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Efficiency 8a, located 50 yards from Ocean, holiday rental in Grassy Key

Efficiency 8a, located 50 yards from Ocean

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Ocean Front House, Pool, 3 Bed/3 Bath, Deep Water Dock, Kayaks, holiday rental in Grassy Key

Ocean Front House, Pool, 3 Bed/3 Bath, Deep Water Dock, Kayaks

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Side Canal Half Duplex, 37' Dock, 600' To Channel, holiday rental in Grassy Key

Ocean Side Canal Half Duplex, 37' Dock, 600' To Channel

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Keys Waterfront Half-Duplex, Ocean side 37' Dock,, holiday rental in Grassy Key

Keys Waterfront Half-Duplex, Ocean side 37' Dock,

1 bedroom
1 bathroom
Sleeps 4
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**WINTER SPECIAL $2999 Rental Rate Any Week Jan-May 2021**, holiday rental in Grassy Key

**WINTER SPECIAL $2999 Rental Rate Any Week Jan-May 2021**

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Casa Solis with 30' dock on the ocean side., holiday rental in Grassy Key

Casa Solis with 30' dock on the ocean side.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Scenic Solitude Private,  Luxurious and tropical Pool Home, holiday rental in Grassy Key

Scenic Solitude Private, Luxurious and tropical Pool Home

4 bedrooms
4 bathrooms
Sleeps 10
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Beautiful Ground Level Home with Open Gulf Views!, holiday rental in Grassy Key

Beautiful Ground Level Home with Open Gulf Views!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Christmas Special **Waterfront/Ocean views, 3 Bedroom, 3 Bath, heated pool Home, holiday rental in Grassy Key

Christmas Special **Waterfront/Ocean views, 3 Bedroom, 3 Bath, heated pool Home

3 bedrooms
3 bathrooms
Sleeps 8
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Water Front Vacation Rental Beautiful Florida Keys, holiday rental in Grassy Key

Water Front Vacation Rental Beautiful Florida Keys

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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3 Bedroom 2.5 Bath Pool Home with Canal Frontage, holiday rental in Grassy Key

3 Bedroom 2.5 Bath Pool Home with Canal Frontage

3 bedrooms
3 bathrooms
Sleeps 7
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Luxurious waterfront home w/panoramic views, pool/spa & dock, holiday rental in Grassy Key

Luxurious waterfront home w/panoramic views, pool/spa & dock

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy the keys updated 3/2home on a canal in marathon 7 day min disc for 30days+, holiday rental in Grassy Key

Enjoy the keys updated 3/2home on a canal in marathon 7 day min disc for 30days+

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunny's Paradise - Beautiful & Clean Canal Front Home That Is Dog Friendly, Brin, holiday rental in Grassy Key

Sunny's Paradise - Beautiful & Clean Canal Front Home That Is Dog Friendly, Brin

2 bedrooms
2 bathrooms
Sleeps 6
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Slice of Paradise,  Beautiful home on a canal. 3 bedrooms and 2 bathrooms., holiday rental in Grassy Key

Slice of Paradise, Beautiful home on a canal. 3 bedrooms and 2 bathrooms.

3 bedrooms
2 bathrooms
Sleeps 8
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Cozy Canal-Front House w/Free WiFi and Deck- Close to Beaches and State Park, holiday rental in Grassy Key

Cozy Canal-Front House w/Free WiFi and Deck- Close to Beaches and State Park

2 bedrooms
2 bathrooms
Sleeps 6
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Indigo Reef Gulfside Villa 47, holiday rental in Grassy Key

Indigo Reef Gulfside Villa 47

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Living in Paradise!  5 bedrooms, Dockage, Ocean View. Relax, Unwind, Fish, holiday rental in Grassy Key

Luxury Living in Paradise! 5 bedrooms, Dockage, Ocean View. Relax, Unwind, Fish

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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New listing! Newly remodeled for HGTV canal front home w/ private swimming pool!, holiday rental in Grassy Key

New listing! Newly remodeled for HGTV canal front home w/ private swimming pool!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Indigo Reef Resort, Villa 9 with Complimentary Dockage - Lacking Vitamin Sea?, holiday rental in Grassy Key

Indigo Reef Resort, Villa 9 with Complimentary Dockage - Lacking Vitamin Sea?

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Huge screened porch, deep dockage, quick boating access, cute and clean!, holiday rental in Grassy Key

Huge screened porch, deep dockage, quick boating access, cute and clean!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fall specials for this Waterfront Canal Home with 65’ Dock and a swim spa pool, holiday rental in Grassy Key

Fall specials for this Waterfront Canal Home with 65’ Dock and a swim spa pool

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Delightful canalfront home w/ private pool, gas grill, WiFi, and water views!, holiday rental in Grassy Key

Delightful canalfront home w/ private pool, gas grill, WiFi, and water views!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Indigo Reef Resort, Villa 25 with Complimentary Dockage - Your Inlet to Fine Liv, holiday rental in Grassy Key

Indigo Reef Resort, Villa 25 with Complimentary Dockage - Your Inlet to Fine Liv

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Reel Paradise I 2bed/2bath half duplex with brand new private pool, deck & docka, holiday rental in Grassy Key

Reel Paradise I 2bed/2bath half duplex with brand new private pool, deck & docka

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Manatee Oasis 3/2 Ground Level Home w/ Pool & 35` Dock, holiday rental in Grassy Key

Manatee Oasis 3/2 Ground Level Home w/ Pool & 35` Dock

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Perla Blanca One-of-a kind Vacation! 4 bed 5 bath water front boat pool/spa, holiday rental in Grassy Key

Perla Blanca One-of-a kind Vacation! 4 bed 5 bath water front boat pool/spa

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Indigo Reef Resort, Villa 23 with Complimentary Dockage - Salt in the Air, Sand, holiday rental in Grassy Key

Indigo Reef Resort, Villa 23 with Complimentary Dockage - Salt in the Air, Sand

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Shangri-La 3 Bedroom 3 Baths Gulf Front Estate, holiday rental in Grassy Key

Shangri-La 3 Bedroom 3 Baths Gulf Front Estate

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants, holiday rental in Grassy Key

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Get out of the cold Feb.5-12, 2018 in  Florida Keys at Marathon,The Hammocks, holiday rental in Grassy Key

Get out of the cold Feb.5-12, 2018 in Florida Keys at Marathon,The Hammocks

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Castaway 2/2 w/ 50` Ft. Dock on the Atlantic, holiday rental in Grassy Key

Castaway 2/2 w/ 50` Ft. Dock on the Atlantic

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Pirate`s Den 3bed/2bath single family with dockage, holiday rental in Grassy Key

Pirate`s Den 3bed/2bath single family with dockage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Blue Marlin 2/2 Pool home with 35` Dock Easy Access to Atlantic, holiday rental in Grassy Key

Blue Marlin 2/2 Pool home with 35` Dock Easy Access to Atlantic

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Palm Point 3 bed 2bath home with  open water views & dockage, holiday rental in Grassy Key

Palm Point 3 bed 2bath home with open water views & dockage

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waves of the Sea,A True Marathon Gem!! is a Ocean View Home with Dock & Cabana C, holiday rental in Grassy Key

Waves of the Sea,A True Marathon Gem!! is a Ocean View Home with Dock & Cabana C

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Reel Therapy 4  - 1bed/1bath updated half duplex w/ 20` dockage no Trailer Parki, holiday rental in Grassy Key

Reel Therapy 4 - 1bed/1bath updated half duplex w/ 20` dockage no Trailer Parki

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Reel Therapy 2-1bed/1bath updated half duplex w/25` dockage & Trailer Parking, holiday rental in Grassy Key

Reel Therapy 2-1bed/1bath updated half duplex w/25` dockage & Trailer Parking

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Reel Therapy 2&4 -2bed/2bath updated full duplex w/40`dockage & Trailer Parking, holiday rental in Grassy Key

Reel Therapy 2&4 -2bed/2bath updated full duplex w/40`dockage & Trailer Parking

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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R & K’s Marathon Paradise 2/2 Duplex w/35` Dock & Cabana Club Included, holiday rental in Grassy Key

R & K’s Marathon Paradise 2/2 Duplex w/35` Dock & Cabana Club Included

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Reel Paradise II 2bed/2bath half duplex with dockage, holiday rental in Grassy Key

Reel Paradise II 2bed/2bath half duplex with dockage

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SUNNY'S PARADISE - Beautiful & Clean Canal Front Home That Is Dog Friendly, Brin, holiday rental in Grassy Key

SUNNY'S PARADISE - Beautiful & Clean Canal Front Home That Is Dog Friendly, Brin

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perla Blanca Brand New 4 bed 5 bath Pool Jacuzzi kayaks in the Heart of Marathon, holiday rental in Grassy Key

Perla Blanca Brand New 4 bed 5 bath Pool Jacuzzi kayaks in the Heart of Marathon

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Swept Away 3bed/2bath brand new with open water views, private pool & dockage, holiday rental in Grassy Key

Swept Away 3bed/2bath brand new with open water views, private pool & dockage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Breeze Oasis With Excellent Boating Access, holiday rental in Grassy Key

Ocean Breeze Oasis With Excellent Boating Access

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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