Holiday Homes near Southernmost Point
1300 Whitehead Street, Key West, Florida 33040
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
768 rentals in Key West.
KAMP | Rooftop Penthouse On Duval
Condo/Apartment
1.1 kilometres from Southernmost Point
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 Bedroom Suite w/ Outdoor Pool in Old Town Key West
Holiday Rental House
1.9 kilometres from Southernmost Point
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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La Brisa Monthly Rental across the street from Smathers Beach
Condo/Apartment
1.8 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private Pool, Outdoor Shower, Pet Friendly, in Golf Course- 5 min to Beach
Holiday Rental House
6.3 kilometres from Southernmost Point
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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MERMAID COVE - A collection of four units on Duval
Holiday Rental House
0.2 kilometres from Southernmost Point
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Margarita Villa-3 bedroom 3 bath home in prime location w/backyard pool oasis
Holiday Rental House
3.2 kilometres from Southernmost Point
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West
Holiday Rental House
0.8 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet & gated. Pool/Deck/Pet
Holiday Rental House
0.5 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
Holiday Rental House
1.4 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Hyatt Windward Pointe, 2 bedroom Waterfront Condo, 2 Night Stay in December
Condo/Apartment
4.3 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Carey’s Corner | Updated Studio with Heated Pool
Condo/Apartment
0.3 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Old Town main house and guest house one block from Duval Street for the best of
Holiday Rental House
0.5 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Seaport Proximity | Resort w/ Outdoor Pools | Spacious Key West Room w
Holiday Rental House
1.4 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hyatt Beach House Resort Key West 2-bedroom with WiFi, AC
Holiday Rental House
5.5 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Palms and Pool Paradise
Holiday Rental House
1.8 kilometres from Southernmost Point
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Sombrero Reef-Tortugas Harbor Suites | Traveling with a group? Share 2 condos
Condo/Apartment
0.5 kilometres from Southernmost Point
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool
Holiday Rental House
1.0 kilometres from Southernmost Point
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sunny Condo w/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
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Old Town Key West Hideaway with Poolside Fun
Holiday Rental House
1.6 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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As seen on
Dog-friendly condo with pool & hot tub - walk or bike to beach
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Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
Holiday Rental House
1.8 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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3-bedroom condo in Key West with 180 degree Ocean View/Marina View Cold AC
Condo/Apartment
6.9 kilometres from Southernmost Point
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1st year for this gorgeous 4Bd 4Ba all ensuite, 2 parking spots, backyard oasis!
Holiday Rental House
1.3 kilometres from Southernmost Point
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Outstanding Room w/ King Bed & Patio just steps from Duval St - Key West Bliss
Holiday Rental House
0.5 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
Holiday Rental House
1.8 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Key West Condo at Coconut Mallory Resort & Marina
Condo/Apartment
5.1 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
Condo/Apartment
1.6 kilometres from Southernmost Point
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Spacious 2/2 Waterfront Condo w/Pool&Dock
Condo/Apartment
1.6 kilometres from Southernmost Point
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Somewhere on the Beach a dream property all amenities included simply amazing
Condo/Apartment
1.9 kilometres from Southernmost Point
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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As seen on
������������ Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Holiday Rental House
1.4 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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As seen on
Key West Cockadoodle Cottage on Duval
Holiday Rental House
0.2 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!
Holiday Rental House
0.2 kilometres from Southernmost Point
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Maryann's Place - Large Monthly Studio (New Listing)
Holiday Rental House
1.1 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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As seen on
Pilar Cottage | Spectacular Studio w/ Shared Pool
Condo/Apartment
1.6 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.
Holiday Rental House
1.3 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.
Condo/Apartment
1.8 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BLUE ROOSTER ~ Spectacular 4 Bed/4 Bath with Pool and Solarium in Old Town!
Holiday Rental House
1.4 kilometres from Southernmost Point
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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As seen on
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
Condo/Apartment
1.9 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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As seen on
2 Hyatt Sunset Harbor Resort, In Town, Marina
Holiday Rental House
1.6 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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As seen on
️3 Bdrm - Ocean View Every Room-Secluded -Quiet-OCEAN FRONT- 90 FT BALCONY
Condo/Apartment
1.9 kilometres from Southernmost Point
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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As seen on
Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
Condo/Apartment
1.6 kilometres from Southernmost Point
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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As seen on
~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!
Holiday Rental House
0.8 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w/ Pool!
Holiday Rental House
1.3 kilometres from Southernmost Point
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
Holiday Rental House
0.8 kilometres from Southernmost Point
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 2-bedroom house in Key West with Pool
Holiday Rental House
1.1 kilometres from Southernmost Point
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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As seen on
Sleeps 6 | Hyatt | Beachfront | Lux Resort | Pool
Holiday Rental House
5.0 kilometres from Southernmost Point
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
Condo/Apartment
0.3 kilometres from Southernmost Point
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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As seen on
Tortugas Harbor Suite | 1 Bed, 1 Bath condo w/shared pool
Condo/Apartment
0.5 kilometres from Southernmost Point
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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As seen on
Two Bedroom Residence
Condo/Apartment
5.3 kilometres from Southernmost Point
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Botanical Island Delight Key West fantastic discounts for Summer & Fall
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