Floridarentalvacations - Vacation Rentals in Smathers Beach

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From US $272

         

10.0 (188 Reviews)

Condo

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West

• Air Conditioner
• Parking
• Pool

• Key West
• Truman Annex

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From US $563

         

|

8.8 (139 Reviews)

Bed & Breakfast

Amsterdam's Curry Mansion Inn

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Historic Seaport

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From US $462

         

|

10.0 (5 Reviews)

Cottage

Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!

• Air Conditioner
• Parking
• Pool

• Key West
• New Town

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From US $474

         

10.0 (178 Reviews)

House

Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only

• Air Conditioner
• Parking
• Pool

• Key West
• Truman Annex

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From US $258

         

|

9.5 (19 Reviews)

House

Old Town Garden Villas

• Air Conditioner
• Pool
• View

• Key West
• Old Town

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From US $421

         

|

10.0 (5 Reviews)

House

Parrot Perch by Avantstay Old Town Key West w/Shared Pool Week Long Stays Only

• Air Conditioner
• Parking
• Pool

• Key West
• Truman Annex

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From US $1,455

         

10.0 (142 Reviews)

House

NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking

• Air Conditioner
• Parking
• Pool

• Key West
• Uptown - Upper Duval

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From US $277

         

|

10.0 (1 Review)

House

Casa Tranquility by Brightwild

• Air Conditioner
• Parking
• Internet

• Florida
• Key West

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From US $2,325

         

10.0 (1 Review)

House

Capmar House by Brightwild Huge Home Pool

• Parking
• Pet Friendly
• Balcony/Terrace

• Florida
• Key West

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From US $391

         

9.8 (158 Reviews)

Condo

Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews

• Air Conditioner
• Parking
• Pool

• Florida
• Key West

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From US $1,595

         

9.8 (131 Reviews)

House

Luxury 3-Bedroom Waterfront Home with Pool AND Dock!

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Meadows

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From US $1,521

         

9.8 (120 Reviews)

House

Conch style home in Oldtown with private pool AND dock!

• Air Conditioner
• Parking
• Pool

• Key West
• Meadows

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From US $283

         

9.8 (100 Reviews)

Condo

Rent a Piece of Paradise, Best Location on the Island!

• Air Conditioner
• Parking
• Pool

• Key West
• Bahama Village

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From US $517

         

9.8 (94 Reviews)

House

CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!

• Air Conditioner
• Parking
• Pool

• Florida
• Key West

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From US $674

         

9.6 (214 Reviews)

House

PET FRIENDLY! SUMMER SPECIALS ! 3 Bedroom 3 bathroom home. Sleeps 8

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Key West

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From US $3,182

         

9.6 (75 Reviews)

House

STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!

• Air Conditioner
• Parking
• Pool

• Key West
• Historic Seaport

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From US $436

         

10.0 (119 Reviews)

House

Prime location, stunning views from 2 decks—walk or ride to explore the island!

• Air Conditioner
• Parking
• Pool

• Key West
• Bahama Village

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From US $737

         

10.0 (78 Reviews)

Cottage

"Tranquility " At Ann Street Gardens Steps From Duval

• Air Conditioner
• Pool
• TV

• Key West
• Historic Seaport

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From US $1,158

         

10.0 (43 Reviews)

House

Namaste 'The Spirit Within Me Salutes The Spirit Within You'

• Air Conditioner
• Pool
• TV

• Key West
• Historic Seaport

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From US $1,276

         

9.8 (83 Reviews)

Condo

*VILLA ANGELITA @ OLD TOWN* Renovated Condo Off Duval + LAST KEY SERVICES.

• Air Conditioner
• Pet Friendly
• TV

• Key West
• Downtown

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From US $431

         

9.0 (49 Reviews)

Condo

BLUE HEAVEN at The Truman Annex in Key West

• Air Conditioner
• Parking
• Pool

• Key West
• Truman Annex

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From US $703

         

10.0 (206 Reviews)

House

Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach

• Air Conditioner
• Parking
• Pool

• Florida
• Key West

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From US $527

         

10.0 (158 Reviews)

Condo

*FOLLOW THE SUN @ THE BEACH* Ocean Condo/Pool & Tennis + LAST KEY SERVICES.

• Air Conditioner
• Parking
• Pool

• Florida
• Key West

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From US $880

         

10.0 (119 Reviews)

Condo

*ATLANTIC REFLECTIONS @ THE BEACH* Ocean Penthouse/Pool + LAST KEY SERVICES.

• Air Conditioner
• Parking
• Pool

• Florida
• Key West

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★ Pro Tip: Floridarentalvacations makes it easy to compare the best listings on Floridarentalvacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Floridarentalvacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Smathers Beach.