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Grassy Key Vacation Rentals

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5 mi
48 rentals in Grassy Key.
The following properties within 20 miles of Grassy Key match all your filters:
Luxury Waterfront Oasis w Heated Pool and 50' Dock, vacation rental in Grassy Key
Luxury Waterfront Oasis w Heated Pool and 50' Dock, vacation rental in Grassy Key
Luxury Waterfront Oasis w Heated Pool and 50' Dock, vacation rental in Grassy Key

Luxury Waterfront Oasis w Heated Pool and 50' Dock

Rental Home
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Direct Oceanfront Private Paradise - Pool/Spa/Dock, vacation rental in Grassy Key
Direct Oceanfront Private Paradise - Pool/Spa/Dock, vacation rental in Grassy Key
Direct Oceanfront Private Paradise - Pool/Spa/Dock, vacation rental in Grassy Key

Direct Oceanfront Private Paradise - Pool/Spa/Dock

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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P12 - CALL FOR BEST PRICES - Single Family, Direct Ocean Front home with privat, vacation rental in Grassy Key
P12 - CALL FOR BEST PRICES - Single Family, Direct Ocean Front home with privat, vacation rental in Grassy Key
P12 - CALL FOR BEST PRICES - Single Family, Direct Ocean Front home with privat, vacation rental in Grassy Key

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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P48 - CALL FOR BEST PRICES - Charming 2 bedroom, 2 bath pool home with 50 ft of, vacation rental in Grassy Key
P48 - CALL FOR BEST PRICES - Charming 2 bedroom, 2 bath pool home with 50 ft of, vacation rental in Grassy Key
P48 - CALL FOR BEST PRICES - Charming 2 bedroom, 2 bath pool home with 50 ft of, vacation rental in Grassy Key

P48 - CALL FOR BEST PRICES - Charming 2 bedroom, 2 bath pool home with 50 ft of

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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1B/2Ba Seaside Getaway, Pool, Oceanside, vacation rental in Grassy Key
1B/2Ba Seaside Getaway, Pool, Oceanside, vacation rental in Grassy Key
1B/2Ba Seaside Getaway, Pool, Oceanside, vacation rental in Grassy Key

1B/2Ba Seaside Getaway, Pool, Oceanside

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Brand New Build!  Krakens Cove, Marathon FL, vacation rental in Grassy Key
Brand New Build!  Krakens Cove, Marathon FL, vacation rental in Grassy Key
Brand New Build!  Krakens Cove, Marathon FL, vacation rental in Grassy Key

Brand New Build! Krakens Cove, Marathon FL

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Keys Wade 1B/2Bath Pool Clubhouse Patio, vacation rental in Grassy Key
Keys Wade 1B/2Bath Pool Clubhouse Patio, vacation rental in Grassy Key
Keys Wade 1B/2Bath Pool Clubhouse Patio, vacation rental in Grassy Key

Keys Wade 1B/2Bath Pool Clubhouse Patio

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Ocean Potion 1B/2B 3Balconies Ocean View, vacation rental in Grassy Key
Ocean Potion 1B/2B 3Balconies Ocean View, vacation rental in Grassy Key
Ocean Potion 1B/2B 3Balconies Ocean View, vacation rental in Grassy Key

Ocean Potion 1B/2B 3Balconies Ocean View

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ground level house with pool and canal to ocean, vacation rental in Grassy Key
Ground level house with pool and canal to ocean, vacation rental in Grassy Key
Ground level house with pool and canal to ocean, vacation rental in Grassy Key

Ground level house with pool and canal to ocean

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

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lo-Key 1: Discover Your Slice of Paradise, Charming Marathon Home, Pool, Deck, vacation rental in Grassy Key
Lo-Key 1: Discover Your Slice of Paradise, Charming Marathon Home, Pool, Deck, vacation rental in Grassy Key
Lo-Key 1: Discover Your Slice of Paradise, Charming Marathon Home, Pool, Deck, vacation rental in Grassy Key

Lo-Key 1: Discover Your Slice of Paradise, Charming Marathon Home, Pool, Deck

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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It’s all here for you. Lagoon, pool, sun deck, kayaks, sunsets., vacation rental in Grassy Key
It’s all here for you. Lagoon, pool, sun deck, kayaks, sunsets., vacation rental in Grassy Key
It’s all here for you. Lagoon, pool, sun deck, kayaks, sunsets., vacation rental in Grassy Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pelagic Retreat  POOL Excellent Boating Access Vaca Cut & Gulf Updated 2 Bedroom, vacation rental in Grassy Key
Pelagic Retreat  POOL Excellent Boating Access Vaca Cut & Gulf Updated 2 Bedroom, vacation rental in Grassy Key
Pelagic Retreat  POOL Excellent Boating Access Vaca Cut & Gulf Updated 2 Bedroom, vacation rental in Grassy Key

Pelagic Retreat POOL Excellent Boating Access Vaca Cut & Gulf Updated 2 Bedroom

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Canalfront home with private pool, dock, central AC, fast WiFi, washer/dryer, vacation rental in Grassy Key
Canalfront home with private pool, dock, central AC, fast WiFi, washer/dryer, vacation rental in Grassy Key
Canalfront home with private pool, dock, central AC, fast WiFi, washer/dryer, vacation rental in Grassy Key

Canalfront home with private pool, dock, central AC, fast WiFi, washer/dryer

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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P60 - 4 bedroom 4 bathroom home with pool and dockage. Amazing outside living..., vacation rental in Grassy Key
P60 - 4 bedroom 4 bathroom home with pool and dockage. Amazing outside living..., vacation rental in Grassy Key
P60 - 4 bedroom 4 bathroom home with pool and dockage. Amazing outside living..., vacation rental in Grassy Key

P60 - 4 bedroom 4 bathroom home with pool and dockage. Amazing outside living...

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Brand New Modern*4Bed4Ba*Private Dock+Heated Pool!, vacation rental in Grassy Key
Brand New Modern*4Bed4Ba*Private Dock+Heated Pool!, vacation rental in Grassy Key
Brand New Modern*4Bed4Ba*Private Dock+Heated Pool!, vacation rental in Grassy Key

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Casa Playa ~ Luxury Waterfront Pool Home w/ 36` Dock!, vacation rental in Grassy Key
Casa Playa ~ Luxury Waterfront Pool Home w/ 36` Dock!, vacation rental in Grassy Key
Casa Playa ~ Luxury Waterfront Pool Home w/ 36` Dock!, vacation rental in Grassy Key

Casa Playa ~ Luxury Waterfront Pool Home w/ 36` Dock!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Perla Blanca 4 Bed 5 Bath kayaks pool boat dock, vacation rental in Grassy Key
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock, vacation rental in Grassy Key
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock, vacation rental in Grassy Key

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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SeaBreeze 6 Bedroom Ocean Side | 6 Bed, 4 Bath, vacation rental in Grassy Key
SeaBreeze 6 Bedroom Ocean Side | 6 Bed, 4 Bath, vacation rental in Grassy Key
SeaBreeze 6 Bedroom Ocean Side | 6 Bed, 4 Bath, vacation rental in Grassy Key

SeaBreeze 6 Bedroom Ocean Side | 6 Bed, 4 Bath

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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3 Bedroom 2.5 Bathroom POOL home with Canal Frontage, vacation rental in Grassy Key
3 Bedroom 2.5 Bathroom POOL home with Canal Frontage, vacation rental in Grassy Key
3 Bedroom 2.5 Bathroom POOL home with Canal Frontage, vacation rental in Grassy Key

3 Bedroom 2.5 Bathroom POOL home with Canal Frontage

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Paradise, vacation rental in Grassy Key
Perfect Paradise, vacation rental in Grassy Key
Perfect Paradise, vacation rental in Grassy Key

Perfect Paradise

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private pool, boat dock, water view, canal front, fully equipped kitchen, vacation rental in Grassy Key
Private pool, boat dock, water view, canal front, fully equipped kitchen, vacation rental in Grassy Key
Private pool, boat dock, water view, canal front, fully equipped kitchen, vacation rental in Grassy Key

Private pool, boat dock, water view, canal front, fully equipped kitchen

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Best Catch on Grouper LN at Ocean Isles, vacation rental in Grassy Key
Best Catch on Grouper LN at Ocean Isles, vacation rental in Grassy Key
Best Catch on Grouper LN at Ocean Isles, vacation rental in Grassy Key

Best Catch on Grouper LN at Ocean Isles

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront home with Direct Atlantic Ocean access, vacation rental in Grassy Key
Waterfront home with Direct Atlantic Ocean access, vacation rental in Grassy Key
Waterfront home with Direct Atlantic Ocean access, vacation rental in Grassy Key

Waterfront home with Direct Atlantic Ocean access

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Dog-friendly waterfront retreat with dock, private pool, washer/dryer, patio, vacation rental in Grassy Key
Dog-friendly waterfront retreat with dock, private pool, washer/dryer, patio, vacation rental in Grassy Key
Dog-friendly waterfront retreat with dock, private pool, washer/dryer, patio, vacation rental in Grassy Key

Dog-friendly waterfront retreat with dock, private pool, washer/dryer, patio

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool, vacation rental in Grassy Key
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool, vacation rental in Grassy Key
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool, vacation rental in Grassy Key

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Escape to Paradise at Ocean Isles Fishing Village!, vacation rental in Grassy Key
Escape to Paradise at Ocean Isles Fishing Village!, vacation rental in Grassy Key
Escape to Paradise at Ocean Isles Fishing Village!, vacation rental in Grassy Key

Escape to Paradise at Ocean Isles Fishing Village!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Discover paradise in this bay view tropical oasis for the perfect Keys gateway, vacation rental in Grassy Key
Discover paradise in this bay view tropical oasis for the perfect Keys gateway, vacation rental in Grassy Key
Discover paradise in this bay view tropical oasis for the perfect Keys gateway, vacation rental in Grassy Key

Discover paradise in this bay view tropical oasis for the perfect Keys gateway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gated Oceanfront Heated Pool, vacation rental in Grassy Key
Gated Oceanfront Heated Pool, vacation rental in Grassy Key
Gated Oceanfront Heated Pool, vacation rental in Grassy Key

Gated Oceanfront Heated Pool

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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La Palma Verde 4bed/4 bath with pool and dockage plus 2 kayaks, vacation rental in Grassy Key
La Palma Verde 4bed/4 bath with pool and dockage plus 2 kayaks, vacation rental in Grassy Key
La Palma Verde 4bed/4 bath with pool and dockage plus 2 kayaks, vacation rental in Grassy Key

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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IB60  Catch n` Relax | 2 Bed, 2.5 Bath, vacation rental in Grassy Key
IB60  Catch n` Relax | 2 Bed, 2.5 Bath, vacation rental in Grassy Key
IB60  Catch n` Relax | 2 Bed, 2.5 Bath, vacation rental in Grassy Key

IB60 Catch n` Relax | 2 Bed, 2.5 Bath

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Steps to the Ocean & Heated Pool, vacation rental in Grassy Key
Steps to the Ocean & Heated Pool, vacation rental in Grassy Key
Steps to the Ocean & Heated Pool, vacation rental in Grassy Key

Steps to the Ocean & Heated Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Discover Your Bliss. Your Tropical Waterfront Paradise Awaits!", vacation rental in Grassy Key
Discover Your Bliss. Your Tropical Waterfront Paradise Awaits!", vacation rental in Grassy Key
Discover Your Bliss. Your Tropical Waterfront Paradise Awaits!", vacation rental in Grassy Key

Discover Your Bliss. Your Tropical Waterfront Paradise Awaits!"

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxurious Tropical Retreat with Private Tiki Hut, vacation rental in Grassy Key
Luxurious Tropical Retreat with Private Tiki Hut, vacation rental in Grassy Key
Luxurious Tropical Retreat with Private Tiki Hut, vacation rental in Grassy Key

Luxurious Tropical Retreat with Private Tiki Hut

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gorgeous Ocean View Home!, vacation rental in Grassy Key
Gorgeous Ocean View Home!, vacation rental in Grassy Key
Gorgeous Ocean View Home!, vacation rental in Grassy Key

Gorgeous Ocean View Home!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ocean Isles #98 ~ Fishing Village ~ Brand New Waterfront Condo w/ Pool!, vacation rental in Grassy Key
Ocean Isles #98 ~ Fishing Village ~ Brand New Waterfront Condo w/ Pool!, vacation rental in Grassy Key
Ocean Isles #98 ~ Fishing Village ~ Brand New Waterfront Condo w/ Pool!, vacation rental in Grassy Key

Ocean Isles #98 ~ Fishing Village ~ Brand New Waterfront Condo w/ Pool!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Relax & unwind in quiet Butterfly Garden, lounge on lanai, ocean view, & hot tub, vacation rental in Grassy Key
Relax & unwind in quiet Butterfly Garden, lounge on lanai, ocean view, & hot tub, vacation rental in Grassy Key
Relax & unwind in quiet Butterfly Garden, lounge on lanai, ocean view, & hot tub, vacation rental in Grassy Key

Relax & unwind in quiet Butterfly Garden, lounge on lanai, ocean view, & hot tub

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Snowbird-friendly condo in oceanfront complex with heated pool, BBQ, W/D, AC, vacation rental in Grassy Key
Snowbird-friendly condo in oceanfront complex with heated pool, BBQ, W/D, AC, vacation rental in Grassy Key
Snowbird-friendly condo in oceanfront complex with heated pool, BBQ, W/D, AC, vacation rental in Grassy Key

Snowbird-friendly condo in oceanfront complex with heated pool, BBQ, W/D, AC

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Blue Bungalow New Listing Canal Front Dock Pool, vacation rental in Grassy Key
Blue Bungalow New Listing Canal Front Dock Pool, vacation rental in Grassy Key
Blue Bungalow New Listing Canal Front Dock Pool, vacation rental in Grassy Key

Blue Bungalow New Listing Canal Front Dock Pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Lovely 3bed 2 bath Beautiful Water Views, Ocean Access, Pool, Tiki,, vacation rental in Grassy Key
Lovely 3bed 2 bath Beautiful Water Views, Ocean Access, Pool, Tiki,, vacation rental in Grassy Key
Lovely 3bed 2 bath Beautiful Water Views, Ocean Access, Pool, Tiki,, vacation rental in Grassy Key

Lovely 3bed 2 bath Beautiful Water Views, Ocean Access, Pool, Tiki,

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Atlantic Breeze NEW 1Bed 2Bath Condo, vacation rental in Grassy Key
Atlantic Breeze NEW 1Bed 2Bath Condo, vacation rental in Grassy Key
Atlantic Breeze NEW 1Bed 2Bath Condo, vacation rental in Grassy Key

Atlantic Breeze NEW 1Bed 2Bath Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Paradise Palms: Movie Theater - Pool - Hot Tub - Boat/RV Parking, vacation rental in Grassy Key
Paradise Palms: Movie Theater - Pool - Hot Tub - Boat/RV Parking, vacation rental in Grassy Key
Paradise Palms: Movie Theater - Pool - Hot Tub - Boat/RV Parking, vacation rental in Grassy Key

Paradise Palms: Movie Theater - Pool - Hot Tub - Boat/RV Parking

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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4 Bed 5 Bath 75ftDock DeepWater Canal Private SaltWater Heated Pool Kayaks Bikes, vacation rental in Grassy Key
4 Bed 5 Bath 75ftDock DeepWater Canal Private SaltWater Heated Pool Kayaks Bikes, vacation rental in Grassy Key
4 Bed 5 Bath 75ftDock DeepWater Canal Private SaltWater Heated Pool Kayaks Bikes, vacation rental in Grassy Key

4 Bed 5 Bath 75ftDock DeepWater Canal Private SaltWater Heated Pool Kayaks Bikes

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Carney's Reef 1B/1B Pool, Large Patio &Living Room, vacation rental in Grassy Key
Carney's Reef 1B/1B Pool, Large Patio &Living Room, vacation rental in Grassy Key
Carney's Reef 1B/1B Pool, Large Patio &Living Room, vacation rental in Grassy Key

Carney's Reef 1B/1B Pool, Large Patio &Living Room

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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6BR/5BA Pelican's Nest: Oceanfront Home With Pool, Tiki Bar, and 150' Boat, vacation rental in Grassy Key
6BR/5BA Pelican's Nest: Oceanfront Home With Pool, Tiki Bar, and 150' Boat, vacation rental in Grassy Key
6BR/5BA Pelican's Nest: Oceanfront Home With Pool, Tiki Bar, and 150' Boat, vacation rental in Grassy Key

6BR/5BA Pelican's Nest: Oceanfront Home With Pool, Tiki Bar, and 150' Boat

Rental Home
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Luxury Oceanfront Mansion, Infinity Pool W/Spa, Dock, vacation rental in Grassy Key
Luxury Oceanfront Mansion, Infinity Pool W/Spa, Dock, vacation rental in Grassy Key
Luxury Oceanfront Mansion, Infinity Pool W/Spa, Dock, vacation rental in Grassy Key

Luxury Oceanfront Mansion, Infinity Pool W/Spa, Dock

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Private Pool & Dock, Stunning Waterfront Home!, vacation rental in Grassy Key
Private Pool & Dock, Stunning Waterfront Home!, vacation rental in Grassy Key
Private Pool & Dock, Stunning Waterfront Home!, vacation rental in Grassy Key

Private Pool & Dock, Stunning Waterfront Home!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Be The First! SPECIAL PRICING! Brand New Beach Home! Ocean Isles 38 Florida KEYS, vacation rental in Grassy Key
Be The First! SPECIAL PRICING! Brand New Beach Home! Ocean Isles 38 Florida KEYS, vacation rental in Grassy Key
Be The First! SPECIAL PRICING! Brand New Beach Home! Ocean Isles 38 Florida KEYS, vacation rental in Grassy Key

Be The First! SPECIAL PRICING! Brand New Beach Home! Ocean Isles 38 Florida KEYS

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-48 of 48
Frequently Asked Questions about Grassy Key