Holiday Homes near Smathers Beach
2601 S Roosevelt Blvd, Key West, Florida 33040-5117
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
858 rentals in Key West.
Pool, Laundry, and grilling area
Holiday Rental House
2.9 kilometres from Smathers Beach
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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**SPIRIT OF KEY WEST * OLD TOWN** Exquisite Home & Pool + LAST KEY SERVICES…
Holiday Rental House
2.4 kilometres from Smathers Beach
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w/boat slip for rent
Condo/Apartment
3.5 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Colorful waterfront condo with pool & hot tub, AC, W/D, & WiFi - dogs OK
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Beach Club #112 - Unique Oceanfront living
Condo/Apartment
1.3 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Ultimate Beach Escape! 3 Pools, Bike Rental, Nightlife, Near Jackson Square!
Holiday Rental House
2.7 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Serenity Retreat- 2/2 townhouse with pool and dock
Holiday Rental House
1.6 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Parking, Pool & Pet Friendly - Larkshine House
Holiday Rental House
4.5 kilometres from Smathers Beach
8 bedrooms
9 bathrooms
Sleeps 18
Match: Sleeps
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������������ Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Holiday Rental House
3.9 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Keys to Paradise by AvantStay | Balcony, Pool, Golf
Holiday Rental House
3.5 kilometres from Smathers Beach
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Location for Your Staycation! Spacious Deluxe Room w/ Pool View
Holiday Rental House
2.6 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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OSPREY STUDIO * The Colony-Sleeps up to 4
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Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
Holiday Rental House
3.9 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2 x Partial Ocean View Balcony 2 Queen Beds Rooms at Southernmost Beach Resort
Holiday Rental House
2.7 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Key West Vintage Luxury Cottage on Duval w Pool
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Castaway Cove: Charming 2BR Townhome in New Town, Key West with Shared Pool
Holiday Rental House
1.8 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Boater's Delight 10 Miles from Key West!
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Historic Inn: Romantic Stay in Key West's Hidden Gem - Pools & Patio
Holiday Rental House
2.7 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Key West/Surrounded by The Atlantic Ocean Includes 42 Ft Dock Space
Holiday Rental House
13.4 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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**CASA AVILA * OLD TOWN** Private Home & Pool + LAST KEY SERVICES…
Holiday Rental House
3.4 kilometres from Smathers Beach
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hyatt 2-bedroom resort in delightful Key West with WiFi, AC
Holiday Rental House
1.9 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Harbor Resort & Spa, Hot Tub, Pool
Holiday Rental House
3.9 kilometres from Smathers Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serene Key West Studio with Poolside Peace
Condo/Apartment
2.6 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious 2/2 Waterfront Condo w/Pool&Dock
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Relaxing Key West Haven with Full-Service Spa and Legendary Dining
Holiday Rental House
3.9 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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By the Beautiful Sea - Key West Beach Front Condo - w Pool Access
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Combined Bayview Manor and Bayview Retreat, accommodating up to 22 guests!
Holiday Rental House
2.1 kilometres from Smathers Beach
9 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Perfect Location to Key West Action! Pool and Garden View Room w/ Balcony
Holiday Rental House
3.4 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Deckside Suite - Efficiency at its finest!
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Laidback Oceanfront Bar and Recreation Area! 2 Convenient Units, Onsite Pool
Holiday Rental House
2.7 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Butterfly Nest - Pool View Condo w/ Pvt Balcony
Condo/Apartment
1.8 kilometres from Smathers Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Holiday Rental House
3.1 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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King Bed Room in the Heart of Key West! Perfect for Friends & Couples Vacation
Holiday Rental House
3.2 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lovely 2 bedroom, 2 bathroom steps from the beach!
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Authentic Florida Experience! Nightlife, Spa, Oceanfront Pool, Beach Access!
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Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West
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Come escape to Island Time Hideaway - Wonderful monthly renovated rental
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Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval! Shared Pool
Condo/Apartment
3.5 kilometres from Smathers Beach
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Luxury Super Yacht
Holiday Rental House
3.1 kilometres from Smathers Beach
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront & Heated Pool - Awai's Floating Villa
Holiday Rental House
3.2 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Vibrant Key West Stay w/ Outdoor Pools | Four Rooms w/ Balcony
Holiday Rental House
3.4 kilometres from Smathers Beach
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Key West Oasis-1Br/2Ba Loft Town Home in a Resort
Holiday Rental House
2.6 kilometres from Smathers Beach
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Captain's Daughter: Oversized home for the whole family w/private pool & dock
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Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
Holiday Rental House
3.9 kilometres from Smathers Beach
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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FANTASY FEST WEEK 2023
Condo/Apartment
2.1 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ideal Location! Three Spacious Spaces, Close to Beach, Outdoor Pool
Holiday Rental House
2.6 kilometres from Smathers Beach
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Two Bedroom Residence
Condo/Apartment
2.6 kilometres from Smathers Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!
Holiday Rental House
3.1 kilometres from Smathers Beach
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square
Holiday Rental House
3.9 kilometres from Smathers Beach
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Double Cabin Luxury Power Motor Yacht in Key West
Holiday Rental House
3.4 kilometres from Smathers Beach
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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