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Holiday Rentals near Smathers Beach Key West, FL
Holiday Rentals
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Florida (FL)
Florida Keys
Key West
Holiday Rentals nearby Smathers Beach
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Holiday Rentals near Smathers Beach
2601 S Roosevelt Blvd, Key West, Florida 33040-5117
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2 Guests
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Bedrooms
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Bathrooms
Any
Amenities
Internet or Wifi (832)
Air Conditioning (814)
Washer/Dryer (647)
Other outdoor space (618)
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Suitability
Kid friendly (807)
Pet friendly (333)
Smoking allowed (10)
Elder access (8)
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Property type
Holiday Rental House (550)
Condominium/Apartment (304)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (134)
Boat Available (64)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
The Ernest Hemingway Home and Museum
Fort Zachary Taylor Historic State Park
Key West Butterfly and Nature Conservatory
Mallory Square
Duval Street
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854 rentals
in Key West.
Pool, Laundry, and grilling area
Holiday Rental House
1.8 miles from Smathers Beach
4 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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The Banyan | Concierge | Beach Access | Pool
Holiday Rental House
2.2 miles from Smathers Beach
2 bedrooms
1 bathroom
Sleeps 6
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Sea Breeze Suite 101 - Dog-friendly, pool, reserved parking!
Condo/Apartment
1.1 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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Tropical Village: Tropical Hideaway - Quiet & gated. Hot tub/Pool/Patio
Holiday Rental House
1.5 miles from Smathers Beach
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Pool View Three Bedroom Residence
Condo/Apartment
1.6 miles from Smathers Beach
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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The Andros | Incredible Views w/ Shared Pool
Condo/Apartment
1.1 miles from Smathers Beach
3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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Castaway Cove: 2/2 Condo near the beach with shared pool and hot tub
5
Condo/Apartment
1.3 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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Charming 4-bedroom house with pool & spa- 10 MIN. WALK TO DUVAL STREET
Holiday Rental House
2.1 miles from Smathers Beach
4 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
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Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.
2
Condo/Apartment
0.7 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Double Cabin Luxury Power Motor Yacht in Key West
Holiday Rental House
2.1 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
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Penny' s Perfect Place
Holiday Rental House
1.6 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Fantastic Land and Sea Vacation! 2 Spacious Rooms, Close to Nearest Beach
Holiday Rental House
1.6 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 8
Match:
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African Queen | Perfect Suite Near Historic Seaport, Shared Pool!
Condo/Apartment
2.2 miles from Smathers Beach
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Speakeasy Inn -Room 1B-1 Queen Bed
Condo/Apartment
1.8 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Thirsty Mermaid - Large 4/3 Pool Home
10
Holiday Rental House
1.0 miles from Smathers Beach
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Welcome to a Sun-Soaked Paradise! Discover the History and Soul of Key West!
Holiday Rental House
1.7 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Parrot Key Resort-Key West, Beach, Pool, Hot Tub
Holiday Rental House
1.0 miles from Smathers Beach
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Welcoming 2 Queen Room w/ Patio- Heart of Key West
Holiday Rental House
2.0 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Comfortable Family Resort Room w/ Ocean Views, Kayak Rentals & Six Pools
Holiday Rental House
2.6 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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2 Oceanfront Two Queen, Pier House Resort, Beach Access, Pet-Friendly, Duval St.
Holiday Rental House
2.4 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Truman Annex end-unit home, private outdoor spaces, pool, close to Duval & beach
9
Holiday Rental House
2.3 miles from Smathers Beach
2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK
19
Holiday Rental House
1.9 miles from Smathers Beach
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Atlantis House's Banyan Suite-voted top 25 in USA
Condo/Apartment
0.9 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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STUNNING! HEART OF OLD TOWN!: Walk to Duval and Historic Seaport in minutes.
Condo/Apartment
2.0 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Snowbird-friendly oasis with private heated pool, lush yard, & ample parking
Holiday Rental House
1.9 miles from Smathers Beach
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Perfect Staycation! Two Convenient Rooms, Onsite Pool, Minutes to Closest Beach
Holiday Rental House
1.6 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Cat Island Suite | Beautifully Renovated w/ Pool!
Condo/Apartment
1.1 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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In the heart of Old Town lies the HAVEN HOUSE
Holiday Rental House
1.8 miles from Smathers Beach
1 bedroom
2 bathrooms
Sleeps 2
Match:
Sleeps
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Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
121
Condo/Apartment
0.5 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Rooftop Penthouse, Walk to Duval - KAMP
2
Condo/Apartment
2.1 miles from Smathers Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Casa Del Mar 2 Bedroom Ocean Front open Feb 1st 2025 onwards. Monthly only
1
Condo/Apartment
0.5 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Pool View Three Bedroom Residence
Condo/Apartment
1.6 miles from Smathers Beach
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
23
Condo/Apartment
0.5 miles from Smathers Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Combined Bayview Manor and Bayview Retreat, accommodating up to 22 guests!
1
Holiday Rental House
1.3 miles from Smathers Beach
9 bedrooms
7 bathrooms
Sleeps 22
Match:
Sleeps
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Margarita Cottage ~ Popular island retreat
26
Holiday Rental House
1.5 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Great for Family Trips! Short Drive to Southernmost Point & Duval Street!
Holiday Rental House
1.7 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Moongate, a Stylish Studio Retreat near Duval, Pet-Friendly, Gated and Private
Condo/Apartment
1.5 miles from Smathers Beach
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Galleon | Marina | Lux Resort | Pool | Hot Tub
Holiday Rental House
2.3 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Banana Wind at Truman Annex - 2 Bed / 2.5-Bath Condo w/ Shared Pool & Parking
Holiday Rental House
2.4 miles from Smathers Beach
2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Colorful waterfront condo with pool & hot tub, AC, W/D, & WiFi - dogs OK
2
Condo/Apartment
0.4 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Ritaville | New! Waterfront Paradise with Private Pool
Holiday Rental House
7.3 miles from Smathers Beach
4 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps
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Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)
107
Condo/Apartment
0.3 miles from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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No secrets at Pilar's Secret - Just a great location!
29
Holiday Rental House
2.0 miles from Smathers Beach
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Hyatt resort 2-bdr 2 bath Duvale St in Key West with kitchen washer/dryer pool
Condo/Apartment
2.2 miles from Smathers Beach
3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Fantastic Land and Sea Vacation! Outdoor Pool, Short Drive To The Beach!
1
Condo/Apartment
1.6 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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DUPLICATE An Island Retreat with an ocean view
Condo/Apartment
1.8 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Pool View Balcony King at Southernmost Beach Resort
Holiday Rental House
1.7 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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1 Classic King Bed Accommodation at Southernmost Beach Resort
Holiday Rental House
1.7 miles from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Private Pool, Outdoor Shower, Pet Friendly, in Golf Course- 5 min to Beach
Holiday Rental House
2.3 miles from Smathers Beach
2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Sunset Harbor Resort & Spa, Hot Tub, Pool
Holiday Rental House
2.4 miles from Smathers Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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