KEY WEST VACATION RENTALS IN THE HISTORIC DISTRICT

Stay in Old Town Key West

Our historic Key West vacation rentals are located in the heart of Old Town Key West. Key West is famous for its historic charm and old town center. Duval Street, which runs through the center of Old Town Key West, has beautiful, historic architecture with classic Victorian homes and cottages. Throughout Key West, you’ll discover many museums and other relics from its famous past. Every home has its own distinct architecture and rich history. Staying in Key West’s historic district gives you a close glimpse into the past of this special island.

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A Bit of Heaven

A Bit of Heaven

3 3 6 Key West
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A Caribbean Alternative

A Caribbean Alternative

2 2.5 4 Key West
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A Cuban Club Suite

A Cuban Club Suite

2 2 8 Key West
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A Slice of Paradise -Shipyard Palms

A Slice of Paradise -Shipyard Palms

2 1.5 4 Key West
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A Windsong Delight

A Windsong Delight

2 2.5 4 Key West
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Absolutely Paradise

Absolutely Paradise

3 2.5 8 Key West
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Ann Street Cottage

Ann Street Cottage

1 1.5 2 Key West
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Artist Condo @ Duval Square #7

Artist Condo @ Duval Square #7

2 2.5 6 Key West
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Ashe Splashe

Ashe Splashe

2 3 6 Key West
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Bahama Dreams

Bahama Dreams

3 2 6 Key West
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Bali Hideaway

Bali Hideaway

0 1 2 Key West
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Casa Amor

Casa Amor

3 2.5 8 Key West
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Casa Bonita @ Duval Square

Casa Bonita @ Duval Square

2 2.5 6 Key West
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Casa Caribe

Casa Caribe

4 4 8 Key West
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Casa de Cuba

Casa de Cuba

3 2 6 Key West
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Casa Loca

Casa Loca

3 2.5 8 Key West
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CasaBella @ Duval Square

CasaBella @ Duval Square

2 2.5 6 Key West
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Catherine House

Catherine House

2 2 4 Key West
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Ceasar's Paradise

Ceasar's Paradise

5 5.5 10 Key West
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Coconut Cabana

Coconut Cabana

3 2 6 Key West
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Colony Calypso

Colony Calypso

1 1 4 Key West
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Colony Conch Casa

Colony Conch Casa

3 2.5 6 Key West
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Colony Poolside

Colony Poolside

1 1 2 Key West
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Conch Easy Livin'

Conch Easy Livin'

2 3 6 Key West
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Cuban Paradise @ Cuban Club

Cuban Paradise @ Cuban Club

2 2 6 Key West
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Duval Square Courtyard Condo 31

Duval Square Courtyard Condo 31

3 2 8 Key West
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Duval Square Delight

Duval Square Delight

2 2.5 4 Key West
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Duval Square Penthouse

Duval Square Penthouse

4 4.5 10 Key West
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Duval Square Retreat

Duval Square Retreat

2 2.5 4 Key West
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Elizabeth Retreat

Elizabeth Retreat

3 2 6 Key West
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Escape on Fleming

Escape on Fleming

2 1 4 Key West
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Fleming-O

Fleming-O

2 1 6 Key West
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Harveys Haven

Harveys Haven

0 1 2 Key West
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Havana Lane

Havana Lane

2 2 4 Key West
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Hidden Oasis @ Colony

Hidden Oasis @ Colony

1 1 4 Key West
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Hidden Treasure @ Colony

Hidden Treasure @ Colony

2 2 6 Key West
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Island Style @ Colony

Island Style @ Colony

1 1 4 Key West
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La Casa Cubana

La Casa Cubana

1 1.5 6 Key West
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La Casa de Luna

La Casa de Luna

1 1 4 Key West
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Louisa House

Louisa House

4 3.5 8 Key West
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Louisas Hideaway

Louisas Hideaway

3 3 6 Key West
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Mango Cottage

Mango Cottage

3 2 6 Key West
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MANSION @ The Watson House

MANSION @ The Watson House

7 7 14 Key West
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Margaret Street Retreat

Margaret Street Retreat

2 2 6 Key West
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Matisse Studio @ the Galleria

Matisse Studio @ the Galleria

0 1 2 Key West
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Namaste

Namaste

1 2 2 Key West
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Ole' Olivia

Ole' Olivia

4 3.5 8 Key West
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Orange Blossom Suite @ Conch Republic Cottage

Orange Blossom Suite @ Conch Republic Cottage

1 1 4 Key West
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Orchid Suite

Orchid Suite

1 1.5 4 Key West
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Osprey @ Colony

Osprey @ Colony

0 1 4 Key West
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Paradise on Porter

Paradise on Porter

2 2.5 4 Key West
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Paradise Place @ Duval Square

Paradise Place @ Duval Square

2 2.5 6 Key West
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Parrotville

Parrotville

2 2 4 Key West
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Petes Cottages

Petes Cottages

4 2 8 Key West
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Petes East Cottage

Petes East Cottage

2 1 4 Key West
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Petes West Cottage

Petes West Cottage

2 1 4 Key West
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Poolside Hide-Away @ Palm Gardens

Poolside Hide-Away @ Palm Gardens

1 1 4 Key West
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Poolside Paradise @ Tropical Village

Poolside Paradise @ Tropical Village

0 1 2 Key West
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Porchside Paradise @ Conch Republic Cottage

Porchside Paradise @ Conch Republic Cottage

1 1 4 Key West
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Royal Escape

Royal Escape

3 3 10 Key West
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Sunset Suite @ Colony

Sunset Suite @ Colony

1 1 4 Key West
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Thalias Retreat

Thalias Retreat

2 2.5 6 Key West
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The Southern Cross @ Tropical Village

The Southern Cross @ Tropical Village

2 2 6 Key West
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Tiki Beach Too

Tiki Beach Too

2 2 6 Key West
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Toon Hall @ Tropical Village

Toon Hall @ Tropical Village

3 2 10 Key West
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Tranquility On Ann Street

Tranquility On Ann Street

1 1 2 Key West
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Tropical Cottage @ Tropical Village

Tropical Cottage @ Tropical Village

2 2 5 Key West
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Tropical Village

Tropical Village

12 9 30 Key West
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VILLA @ The Watson House

VILLA @ The Watson House

4 4 8 Key West
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Villa Bella

Villa Bella

5 4 12 Key West
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Villa Serena @ Duval Square

Villa Serena @ Duval Square

2 2.5 4 Key West
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Watson House Grand Estate

Watson House Grand Estate

11 11 22 Key West
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Windsor Townhomes #3

Windsor Townhomes #3

3 3.5 6 Key West
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Windsor Townhomes #4

Windsor Townhomes #4

3 3.5 6 Key West
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Windsor Townhomes #5

Windsor Townhomes #5

3 3.5 6 Key West
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Windsor Townhomes #6

Windsor Townhomes #6

3 3.5 6 Key West
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Windward Breeze

Windward Breeze

2 2 4 Key West
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