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Smith Bay Holiday Rentals

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84 rentals in Smith Bay.
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Save15% Sapphire Beach Amazing Beachfront 2 floor Condo, holiday rental in Smith Bay

Save15% Sapphire Beach Amazing Beachfront 2 floor Condo

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Front Villa Lush Property with Private Beach and Lagoon, holiday rental in Smith Bay

Ocean Front Villa Lush Property with Private Beach and Lagoon

6 bedrooms
8 bathrooms
Sleeps 12
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Luxury Oceanfront Villa /Breathtaking Views/ Total Privacy / Close to Red Hook, holiday rental in Smith Bay

Luxury Oceanfront Villa /Breathtaking Views/ Total Privacy / Close to Red Hook

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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New York Designer's Caribbean Hideaway on Sapphire Beach, holiday rental in Smith Bay

New York Designer's Caribbean Hideaway on Sapphire Beach

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Serenity - Private Caribbean-Style Pool Villa:  $250/ nt. or Less!, holiday rental in Smith Bay

Serenity - Private Caribbean-Style Pool Villa: $250/ nt. or Less!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Million Dollar Views: Walk to the Beach, Pools & Restaurant, holiday rental in Smith Bay

Million Dollar Views: Walk to the Beach, Pools & Restaurant

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Resort Romance 1 Bedroom Oceanview Villa (resort privileges), holiday rental in Smith Bay

Resort Romance 1 Bedroom Oceanview Villa (resort privileges)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront, wrap around balc. Great views. Lower $ avail. for longer stay. C6, holiday rental in Smith Bay

Waterfront, wrap around balc. Great views. Lower $ avail. for longer stay. C6

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Warm & Sunny at Tortuga Del Mar - 1 BR Point Pleasant - Great Views!, holiday rental in Smith Bay

Warm & Sunny at Tortuga Del Mar - 1 BR Point Pleasant - Great Views!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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PURPLE LOTUS AT CRYSTAL COVE SAPPHIRE BEACH, holiday rental in Smith Bay

PURPLE LOTUS AT CRYSTAL COVE SAPPHIRE BEACH

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Great Location/views! Wrap around balc. Lower $ avail. for longer stays. B22, holiday rental in Smith Bay

Great Location/views! Wrap around balc. Lower $ avail. for longer stays. B22

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Views! Newly Remodeled 1 BR/1BA Condo w/ WrapAround Balcony! Amazing!, holiday rental in Smith Bay

Stunning Views! Newly Remodeled 1 BR/1BA Condo w/ WrapAround Balcony! Amazing!

1 bedroom
1 bathroom
Sleeps 4
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Edenview Remodeled Luxury Villa- Breathtaking Views!  Perfect 2BR/2BA Book Now!, holiday rental in Smith Bay

Edenview Remodeled Luxury Villa- Breathtaking Views! Perfect 2BR/2BA Book Now!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Views Down Island!  Remodeled 1BR/1BA - Wrap Around Balcony!, holiday rental in Smith Bay

Spectacular Views Down Island! Remodeled 1BR/1BA - Wrap Around Balcony!

1 bedroom
1 bathroom
Sleeps 2
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Top floor luxury, 2 full baths, near pool, Lower $ avail. for longer stays.A1, holiday rental in Smith Bay

Top floor luxury, 2 full baths, near pool, Lower $ avail. for longer stays.A1

1 bedroom
2 bathrooms
Sleeps 6
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You just found your vacation home with breathtaking views! C'est Jolie D-27!, holiday rental in Smith Bay

You just found your vacation home with breathtaking views! C'est Jolie D-27!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Views: 9 Islands, Pools, Beaches and More, holiday rental in Smith Bay

Amazing Views: 9 Islands, Pools, Beaches and More

1 bedroom
1 bathroom
Sleeps 4
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Top fl. luxury,no steps, great views. Lower $ available for longer stays. B20, holiday rental in Smith Bay

Top fl. luxury,no steps, great views. Lower $ available for longer stays. B20

1 bedroom
1 bathroom
Sleeps 4
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Luxury 2 BR, stunning hilltop views. Lower $ avail. for longer stays. D19, holiday rental in Smith Bay

Luxury 2 BR, stunning hilltop views. Lower $ avail. for longer stays. D19

2 bedrooms
2 bathrooms
Sleeps 7
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Luxury, breathtaking views. New! Lower $ available for longer stays.  F5, holiday rental in Smith Bay

Luxury, breathtaking views. New! Lower $ available for longer stays. F5

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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★★★★★Spectacular Water View-Private Wrap-Around Balcony-3 Pools-2 Restaurants ☼☼, holiday rental in Smith Bay

★★★★★Spectacular Water View-Private Wrap-Around Balcony-3 Pools-2 Restaurants ☼☼

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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East End Beautiful Condo next to Margaritaville, holiday rental in Smith Bay

East End Beautiful Condo next to Margaritaville

3 bedrooms
4 bathrooms
Sleeps 8
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Luxury,2 full baths, great location. Lower $ avail. for longer stays. A11, holiday rental in Smith Bay

Luxury,2 full baths, great location. Lower $ avail. for longer stays. A11

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Views  Spacious 2 BR/2BA - sleeps 6! Book Now for Late Summer!, holiday rental in Smith Bay

Stunning Views Spacious 2 BR/2BA - sleeps 6! Book Now for Late Summer!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hilltop views, wrap around balcony. Lower $ available for longer stays. E15, holiday rental in Smith Bay

Hilltop views, wrap around balcony. Lower $ available for longer stays. E15

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beach, Bed and Beyond! Fall/Winter Specials. WiFi, holiday rental in Smith Bay

Beach, Bed and Beyond! Fall/Winter Specials. WiFi

1 bedroom
1 bathroom
Sleeps 4
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Luxury. Great location/views! No steps in.Lower $ avail. for longer stays.B28, holiday rental in Smith Bay

Luxury. Great location/views! No steps in.Lower $ avail. for longer stays.B28

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Top fl. luxury,2 full baths,great location.Lower $ avail. for longer stays.A2, holiday rental in Smith Bay

Top fl. luxury,2 full baths,great location.Lower $ avail. for longer stays.A2

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury, 2 full baths, great location, Lower $ avail. for longer stays. A12, holiday rental in Smith Bay

Luxury, 2 full baths, great location, Lower $ avail. for longer stays. A12

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Taylor's Retreat - Amazing Views! 1BR/1BA Remodeled Book Now for Summer Openings, holiday rental in Smith Bay

Taylor's Retreat - Amazing Views! 1BR/1BA Remodeled Book Now for Summer Openings

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Top fl. waterfront luxury next to beach.Lower $ available for longer stays.B1, holiday rental in Smith Bay

Top fl. waterfront luxury next to beach.Lower $ available for longer stays.B1

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Resort 1 Bedroom Oceanview Villa (resort privileges), holiday rental in Smith Bay

Resort 1 Bedroom Oceanview Villa (resort privileges)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautifully renovated 3 BR/4 BA condo footsteps from the beach, holiday rental in Smith Bay

Beautifully renovated 3 BR/4 BA condo footsteps from the beach

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Resort Premiere 1 BR Oceanview Villa (resort privileges), holiday rental in Smith Bay

Resort Premiere 1 BR Oceanview Villa (resort privileges)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Resort 1 Bedroom Oceanview Villa (resort privileges), holiday rental in Smith Bay

Resort 1 Bedroom Oceanview Villa (resort privileges)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront, pool front, great view. Lower $ available for longer stays.  F6, holiday rental in Smith Bay

Waterfront, pool front, great view. Lower $ available for longer stays. F6

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Resort 1 Bedroom Oceanview Suite (resort privileges), holiday rental in Smith Bay

Resort 1 Bedroom Oceanview Suite (resort privileges)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Top floor waterfront next to beach. Lower $ available for longer stays. B3, holiday rental in Smith Bay

Top floor waterfront next to beach. Lower $ available for longer stays. B3

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront near pool/beach. Lower $ available for longer stays. B10, holiday rental in Smith Bay

Waterfront near pool/beach. Lower $ available for longer stays. B10

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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My Blue Heaven-1 BR/2BA -sleeps 5 -Amazing Views - Spacious, New Remodel!, holiday rental in Smith Bay

My Blue Heaven-1 BR/2BA -sleeps 5 -Amazing Views - Spacious, New Remodel!

1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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Resort 1 Bedroom Oceanview Suite (resort privileges), holiday rental in Smith Bay

Resort 1 Bedroom Oceanview Suite (resort privileges)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury, wrap around balc., amazing views.Lower $ available for longer stay.D2, holiday rental in Smith Bay

Luxury, wrap around balc., amazing views.Lower $ available for longer stay.D2

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Best of both - location/views. Lower $ available for longer stays. B21, holiday rental in Smith Bay

Best of both - location/views. Lower $ available for longer stays. B21

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Updated! 1BR/1BA with Spectacular Views from Balcony -Top Floor Condo, holiday rental in Smith Bay

Newly Updated! 1BR/1BA with Spectacular Views from Balcony -Top Floor Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Your Private Villa & Pool in the sun!, holiday rental in Smith Bay

Your Private Villa & Pool in the sun!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Awesome hilltop views. Lower $ available for longer stays.  D4, holiday rental in Smith Bay

Awesome hilltop views. Lower $ available for longer stays. D4

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury/Views! Wrap around balc. Lower $ available for longer stays. B32, holiday rental in Smith Bay

Luxury/Views! Wrap around balc. Lower $ available for longer stays. B32

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wrap around balc.,near pool and lobby.Lower $ available for longer stays. B16, holiday rental in Smith Bay

Wrap around balc.,near pool and lobby.Lower $ available for longer stays. B16

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Resort 1 Bedroom Oceanview Villa (Resort Privileges), holiday rental in Smith Bay

Resort 1 Bedroom Oceanview Villa (Resort Privileges)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Top floor, great location & views. Lower $ available for longer stays.B27, holiday rental in Smith Bay

Top floor, great location & views. Lower $ available for longer stays.B27

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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