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Villas in Grassy Key

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

40 rentals in Grassy Key.
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, holiday rental in Grassy Key
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

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

Unit 9, Furnished Studio located 50 yards from ocean

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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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, holiday rental in Grassy Key
 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

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

Unit 10, Furnished Studio located 50 yards from ocean

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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, holiday rental in Grassy Key
Efficiency 8a, located 50 yards from Ocean, holiday rental in Grassy Key

Efficiency 8a, located 50 yards from Ocean

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Glamping in the Florida Keys , holiday rental in Grassy Key
Glamping in the Florida Keys , holiday rental in Grassy Key
Glamping in the Florida Keys , holiday rental in Grassy Key

Glamping in the Florida Keys

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxury Waterfront Pool Home Canal Front Direct Ocean Access Fisherman's Paradise, holiday rental in Grassy Key
Luxury Waterfront Pool Home Canal Front Direct Ocean Access Fisherman's Paradise, holiday rental in Grassy Key
Luxury Waterfront Pool Home Canal Front Direct Ocean Access Fisherman's Paradise, holiday rental in Grassy Key

Luxury Waterfront Pool Home Canal Front Direct Ocean Access Fisherman's Paradise

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming 3/2 , Open Water Views, Direct Ocean Access, Pool, Tiki Hut, Near Vaca, holiday rental in Grassy Key
Charming 3/2 , Open Water Views, Direct Ocean Access, Pool, Tiki Hut, Near Vaca, holiday rental in Grassy Key
Charming 3/2 , Open Water Views, Direct Ocean Access, Pool, Tiki Hut, Near Vaca, holiday rental in Grassy Key

Charming 3/2 , Open Water Views, Direct Ocean Access, Pool, Tiki Hut, Near Vaca

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Catherine's Tropical Paradise - Instant Ocean Access, Deep Water Canal, holiday rental in Grassy Key
Catherine's Tropical Paradise - Instant Ocean Access, Deep Water Canal, holiday rental in Grassy Key
Catherine's Tropical Paradise - Instant Ocean Access, Deep Water Canal, holiday rental in Grassy Key

Catherine's Tropical Paradise - Instant Ocean Access, Deep Water Canal

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 Bedroom 2.5 Bathroom POOL home with Canal Frontage, holiday rental in Grassy Key
3 Bedroom 2.5 Bathroom POOL home with Canal Frontage, holiday rental in Grassy Key
3 Bedroom 2.5 Bathroom POOL home with Canal Frontage, holiday rental in Grassy Key

3 Bedroom 2.5 Bathroom POOL home with Canal Frontage

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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��<1 Min to Ocean Sleeps 12 Waterfront Home Ocean Side Deep Canal 68ft Dock, holiday rental in Grassy Key
��<1 Min to Ocean Sleeps 12 Waterfront Home Ocean Side Deep Canal 68ft Dock, holiday rental in Grassy Key
��<1 Min to Ocean Sleeps 12 Waterfront Home Ocean Side Deep Canal 68ft Dock, holiday rental in Grassy Key

��<1 Min to Ocean Sleeps 12 Waterfront Home Ocean Side Deep Canal 68ft Dock

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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SeaBreeze� A Private Pool, Pet Friendly �, holiday rental in Grassy Key
SeaBreeze� A Private Pool, Pet Friendly �, holiday rental in Grassy Key
SeaBreeze� A Private Pool, Pet Friendly �, holiday rental in Grassy Key

SeaBreeze� A Private Pool, Pet Friendly �

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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4 Bed, 5 bath boat dock pool kayaks quick access to the Gulf and Ocean, holiday rental in Grassy Key
4 Bed, 5 bath boat dock pool kayaks quick access to the Gulf and Ocean, holiday rental in Grassy Key
4 Bed, 5 bath boat dock pool kayaks quick access to the Gulf and Ocean, holiday rental in Grassy Key

4 Bed, 5 bath boat dock pool kayaks quick access to the Gulf and Ocean

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious Tropical Retreat with Private Tiki Hut, holiday rental in Grassy Key
Luxurious Tropical Retreat with Private Tiki Hut, holiday rental in Grassy Key
Luxurious Tropical Retreat with Private Tiki Hut, holiday rental in Grassy Key

Luxurious Tropical Retreat with Private Tiki Hut

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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It’s all here for you. Lagoon, pool, sun deck, kayaks, sunsets., holiday rental in Grassy Key
It’s all here for you. Lagoon, pool, sun deck, kayaks, sunsets., holiday rental in Grassy Key
It’s all here for you. Lagoon, pool, sun deck, kayaks, sunsets., holiday rental in Grassy Key

It’s all here for you. Lagoon, pool, sun deck, kayaks, sunsets.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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� *NEW Canal-front Rental ~ boating is a breeze!, holiday rental in Grassy Key
� *NEW Canal-front Rental ~ boating is a breeze!, holiday rental in Grassy Key
� *NEW Canal-front Rental ~ boating is a breeze!, holiday rental in Grassy Key

� *NEW Canal-front Rental ~ boating is a breeze!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Aqua Vista ~ Newly Updated Tropical getaway with Tiki hut!, holiday rental in Grassy Key
Aqua Vista ~ Newly Updated Tropical getaway with Tiki hut!, holiday rental in Grassy Key
Aqua Vista ~ Newly Updated Tropical getaway with Tiki hut!, holiday rental in Grassy Key

Aqua Vista ~ Newly Updated Tropical getaway with Tiki hut!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private waterfront sleeps 8 dock heated pool pets, holiday rental in Grassy Key
Private waterfront sleeps 8 dock heated pool pets, holiday rental in Grassy Key
Private waterfront sleeps 8 dock heated pool pets, holiday rental in Grassy Key

Private waterfront sleeps 8 dock heated pool pets

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pool! Quick Access via Vaca Cut! Dockage, Outdoor Space, Tons of Parking!, holiday rental in Grassy Key
Pool! Quick Access via Vaca Cut! Dockage, Outdoor Space, Tons of Parking!, holiday rental in Grassy Key
Pool! Quick Access via Vaca Cut! Dockage, Outdoor Space, Tons of Parking!, holiday rental in Grassy Key

Pool! Quick Access via Vaca Cut! Dockage, Outdoor Space, Tons of Parking!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront home with Direct Atlantic Ocean access, holiday rental in Grassy Key
Waterfront home with Direct Atlantic Ocean access, holiday rental in Grassy Key
Waterfront home with Direct Atlantic Ocean access, holiday rental in Grassy Key

Waterfront home with Direct Atlantic Ocean access

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Pelagic Retreat! Excellent Boating Access, Newly Updated 2 Bedroom Gulfside Home, holiday rental in Grassy Key
Pelagic Retreat! Excellent Boating Access, Newly Updated 2 Bedroom Gulfside Home, holiday rental in Grassy Key
Pelagic Retreat! Excellent Boating Access, Newly Updated 2 Bedroom Gulfside Home, holiday rental in Grassy Key

Pelagic Retreat! Excellent Boating Access, Newly Updated 2 Bedroom Gulfside Home

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lo-Key 1 - Charming Home In Marathon, Enjoy Your Private Backyard Oasis, Pool, holiday rental in Grassy Key
Lo-Key 1 - Charming Home In Marathon, Enjoy Your Private Backyard Oasis, Pool, holiday rental in Grassy Key
Lo-Key 1 - Charming Home In Marathon, Enjoy Your Private Backyard Oasis, Pool, holiday rental in Grassy Key

Lo-Key 1 - Charming Home In Marathon, Enjoy Your Private Backyard Oasis, Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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La Palma Verde 4bed/4 bath with pool and dockage plus 2 kayaks, holiday rental in Grassy Key
La Palma Verde 4bed/4 bath with pool and dockage plus 2 kayaks, holiday rental in Grassy Key
La Palma Verde 4bed/4 bath with pool and dockage plus 2 kayaks, holiday rental in Grassy Key

La Palma Verde 4bed/4 bath with pool and dockage plus 2 kayaks

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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P51 - CALL FOR BEST PRICES - 2 bedroom 2 bath, single family pool home with dock, holiday rental in Grassy Key
P51 - CALL FOR BEST PRICES - 2 bedroom 2 bath, single family pool home with dock, holiday rental in Grassy Key
P51 - CALL FOR BEST PRICES - 2 bedroom 2 bath, single family pool home with dock, holiday rental in Grassy Key

P51 - CALL FOR BEST PRICES - 2 bedroom 2 bath, single family pool home with dock

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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P12 - CALL FOR BEST PRICES - Single Family, Direct Ocean Front home with privat, holiday rental in Grassy Key
P12 - CALL FOR BEST PRICES - Single Family, Direct Ocean Front home with privat, holiday rental in Grassy Key
P12 - CALL FOR BEST PRICES - Single Family, Direct Ocean Front home with privat, holiday rental in Grassy Key

P12 - CALL FOR BEST PRICES - Single Family, Direct Ocean Front home with privat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Waterfront Home with 33-Foot Dock, Outdoor Shower, Large Patio, & Ideal Location, holiday rental in Grassy Key
Waterfront Home with 33-Foot Dock, Outdoor Shower, Large Patio, & Ideal Location, holiday rental in Grassy Key
Waterfront Home with 33-Foot Dock, Outdoor Shower, Large Patio, & Ideal Location, holiday rental in Grassy Key

Waterfront Home with 33-Foot Dock, Outdoor Shower, Large Patio, & Ideal Location

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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P60 - Brand New 4 bedroom 4 bathroom home with pool and dockage. Amazing..., holiday rental in Grassy Key
P60 - Brand New 4 bedroom 4 bathroom home with pool and dockage. Amazing..., holiday rental in Grassy Key
P60 - Brand New 4 bedroom 4 bathroom home with pool and dockage. Amazing..., holiday rental in Grassy Key

P60 - Brand New 4 bedroom 4 bathroom home with pool and dockage. Amazing...

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Lo-Key 1 - Charming Home In Marathon, Enjoy Your Private Backyard Oasis, Pool, T, holiday rental in Grassy Key
Lo-Key 1 - Charming Home In Marathon, Enjoy Your Private Backyard Oasis, Pool, T, holiday rental in Grassy Key
Lo-Key 1 - Charming Home In Marathon, Enjoy Your Private Backyard Oasis, Pool, T, holiday rental in Grassy Key

Lo-Key 1 - Charming Home In Marathon, Enjoy Your Private Backyard Oasis, Pool, T

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Brand New Modern*4Bed4Ba*Private Dock+Heated Pool!, holiday rental in Grassy Key
Brand New Modern*4Bed4Ba*Private Dock+Heated Pool!, holiday rental in Grassy Key
Brand New Modern*4Bed4Ba*Private Dock+Heated Pool!, holiday rental in Grassy Key

Brand New Modern*4Bed4Ba*Private Dock+Heated Pool!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Shore Thing ~ Exclusive, Luxury Pool Home ~ Kayaks and Bikes included!, holiday rental in Grassy Key
Shore Thing ~ Exclusive, Luxury Pool Home ~ Kayaks and Bikes included!, holiday rental in Grassy Key
Shore Thing ~ Exclusive, Luxury Pool Home ~ Kayaks and Bikes included!, holiday rental in Grassy Key

Shore Thing ~ Exclusive, Luxury Pool Home ~ Kayaks and Bikes included!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
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NEW Pelican&#39;s Nest: Oceanfront Home Featuring Pool, Tiki Bar, and Dockage, holiday rental in Grassy Key
NEW Pelican&#39;s Nest: Oceanfront Home Featuring Pool, Tiki Bar, and Dockage, holiday rental in Grassy Key
NEW Pelican&#39;s Nest: Oceanfront Home Featuring Pool, Tiki Bar, and Dockage, holiday rental in Grassy Key

NEW Pelican&#39;s Nest: Oceanfront Home Featuring Pool, Tiki Bar, and Dockage

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Hammock Hiatus - Quaint 2BR Home in Marathon, Convenient To Everything, Private, holiday rental in Grassy Key
Hammock Hiatus - Quaint 2BR Home in Marathon, Convenient To Everything, Private, holiday rental in Grassy Key
Hammock Hiatus - Quaint 2BR Home in Marathon, Convenient To Everything, Private, holiday rental in Grassy Key

Hammock Hiatus - Quaint 2BR Home in Marathon, Convenient To Everything, Private

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Updated Canal Front, Private Dock, Ocean Side, holiday rental in Grassy Key
Updated Canal Front, Private Dock, Ocean Side, holiday rental in Grassy Key
Updated Canal Front, Private Dock, Ocean Side, holiday rental in Grassy Key

Updated Canal Front, Private Dock, Ocean Side

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Paradise, holiday rental in Grassy Key
Perfect Paradise, holiday rental in Grassy Key
Perfect Paradise, holiday rental in Grassy Key

Perfect Paradise

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hammock Hiatus - Quaint 2BR Home in Marathon, Convenient To Everything, Private, holiday rental in Grassy Key
Hammock Hiatus - Quaint 2BR Home in Marathon, Convenient To Everything, Private, holiday rental in Grassy Key
Hammock Hiatus - Quaint 2BR Home in Marathon, Convenient To Everything, Private, holiday rental in Grassy Key

Hammock Hiatus - Quaint 2BR Home in Marathon, Convenient To Everything, Private

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Oceanside Canal-Front Retreat w/Dock, Free WiFi, Deck, Buoy, Gas Grill, & W/D, holiday rental in Grassy Key
Oceanside Canal-Front Retreat w/Dock, Free WiFi, Deck, Buoy, Gas Grill, & W/D, holiday rental in Grassy Key
Oceanside Canal-Front Retreat w/Dock, Free WiFi, Deck, Buoy, Gas Grill, & W/D, holiday rental in Grassy Key

Oceanside Canal-Front Retreat w/Dock, Free WiFi, Deck, Buoy, Gas Grill, & W/D

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Amazing Sunsets from your private pool, sundeck and ocean access dock., holiday rental in Grassy Key
Amazing Sunsets from your private pool, sundeck and ocean access dock., holiday rental in Grassy Key
Amazing Sunsets from your private pool, sundeck and ocean access dock., holiday rental in Grassy Key

Amazing Sunsets from your private pool, sundeck and ocean access dock.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Canal front getaway in the heart of Marathon with WiFi, furnished deck, and AC, holiday rental in Grassy Key
Canal front getaway in the heart of Marathon with WiFi, furnished deck, and AC, holiday rental in Grassy Key
Canal front getaway in the heart of Marathon with WiFi, furnished deck, and AC, holiday rental in Grassy Key

Canal front getaway in the heart of Marathon with WiFi, furnished deck, and AC

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Butterfly Cottage, holiday rental in Grassy Key
The Butterfly Cottage, holiday rental in Grassy Key
The Butterfly Cottage, holiday rental in Grassy Key

The Butterfly Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ground level house with pool and canal to ocean, holiday rental in Grassy Key
Ground level house with pool and canal to ocean, holiday rental in Grassy Key
Ground level house with pool and canal to ocean, holiday rental in Grassy Key

Ground level house with pool and canal to ocean

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-40 of 40
Frequently Asked Questions about Grassy Key