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Holiday Rentals in Key West

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187 rentals in Key West.
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6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location, holiday rental in Key West
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location, holiday rental in Key West
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location, holiday rental in Key West

6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean View Estate with Private Pool 15 minutes from Key West , holiday rental in Key West
Ocean View Estate with Private Pool 15 minutes from Key West , holiday rental in Key West
Ocean View Estate with Private Pool 15 minutes from Key West , holiday rental in Key West

Ocean View Estate with Private Pool 15 minutes from Key West

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West
Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West
Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West

Casa Del Sol, a Key West Vacation (Truman Annex)

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Artist Cottage in Truman Annex, holiday rental in Key West
Artist Cottage in Truman Annex, holiday rental in Key West
Artist Cottage in Truman Annex, holiday rental in Key West

Artist Cottage in Truman Annex

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 8, holiday rental in Key West
Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 8, holiday rental in Key West
Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 8, holiday rental in Key West

Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 8

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access, holiday rental in Key West
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access, holiday rental in Key West
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access, holiday rental in Key West

Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!, holiday rental in Key West
Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!, holiday rental in Key West
Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!, holiday rental in Key West

Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST., holiday rental in Key West
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST., holiday rental in Key West
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST., holiday rental in Key West

STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi, holiday rental in Key West
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi, holiday rental in Key West
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi, holiday rental in Key West

Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Attitude Key West (2 Bikes and Wireless Internet), holiday rental in Key West
Attitude Key West (2 Bikes and Wireless Internet), holiday rental in Key West
Attitude Key West (2 Bikes and Wireless Internet), holiday rental in Key West

Attitude Key West (2 Bikes and Wireless Internet)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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My Condo by the Beach with Ocean View, holiday rental in Key West
My Condo by the Beach with Ocean View, holiday rental in Key West
My Condo by the Beach with Ocean View, holiday rental in Key West

My Condo by the Beach with Ocean View

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sea Breeze Cottage- in Beautiful Truman Annex, holiday rental in Key West
Sea Breeze Cottage- in Beautiful Truman Annex, holiday rental in Key West
Sea Breeze Cottage- in Beautiful Truman Annex, holiday rental in Key West

Sea Breeze Cottage- in Beautiful Truman Annex

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2022 IS THE FINAL YEAR.  Giving it to a vacation rental company for 2023., holiday rental in Key West
2022 IS THE FINAL YEAR.  Giving it to a vacation rental company for 2023., holiday rental in Key West
2022 IS THE FINAL YEAR.  Giving it to a vacation rental company for 2023., holiday rental in Key West

2022 IS THE FINAL YEAR. Giving it to a vacation rental company for 2023.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Catherine House: A charming Old Town Key West cottage, holiday rental in Key West
Catherine House: A charming Old Town Key West cottage, holiday rental in Key West
Catherine House: A charming Old Town Key West cottage, holiday rental in Key West

Catherine House: A charming Old Town Key West cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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William Skelton House - Available Easter Weekend!, holiday rental in Key West
William Skelton House - Available Easter Weekend!, holiday rental in Key West
William Skelton House - Available Easter Weekend!, holiday rental in Key West

William Skelton House - Available Easter Weekend!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Seaside Place Key West FL 5 Bedroom House 4 Baths, holiday rental in Key West
Seaside Place Key West FL 5 Bedroom House 4 Baths, holiday rental in Key West
Seaside Place Key West FL 5 Bedroom House 4 Baths, holiday rental in Key West

Seaside Place Key West FL 5 Bedroom House 4 Baths

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna, holiday rental in Key West
Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna, holiday rental in Key West
Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna, holiday rental in Key West

Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Boli Townhouse - Luxury Rental in gated Truman Annex, holiday rental in Key West
Boli Townhouse - Luxury Rental in gated Truman Annex, holiday rental in Key West
Boli Townhouse - Luxury Rental in gated Truman Annex, holiday rental in Key West

Boli Townhouse - Luxury Rental in gated Truman Annex

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Top Floor Ocean Views from every window Olympic Size Pool-Jacuzzi- Sauna-Tennis, holiday rental in Key West
Top Floor Ocean Views from every window Olympic Size Pool-Jacuzzi- Sauna-Tennis, holiday rental in Key West
Top Floor Ocean Views from every window Olympic Size Pool-Jacuzzi- Sauna-Tennis, holiday rental in Key West

Top Floor Ocean Views from every window Olympic Size Pool-Jacuzzi- Sauna-Tennis

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex, holiday rental in Key West
Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex, holiday rental in Key West
Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex, holiday rental in Key West

Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Mermaids House, Historic Old Town Key West, holiday rental in Key West
The Mermaids House, Historic Old Town Key West, holiday rental in Key West
The Mermaids House, Historic Old Town Key West, holiday rental in Key West

The Mermaids House, Historic Old Town Key West

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Duval Square Penthouse: A large, beautiful condo steps from the action, holiday rental in Key West
Duval Square Penthouse: A large, beautiful condo steps from the action, holiday rental in Key West
Duval Square Penthouse: A large, beautiful condo steps from the action, holiday rental in Key West

Duval Square Penthouse: A large, beautiful condo steps from the action

Condo/Apartment
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!, holiday rental in Key West
'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!, holiday rental in Key West
'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!, holiday rental in Key West

'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West
Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West
Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi, holiday rental in Key West
Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi, holiday rental in Key West
Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi, holiday rental in Key West

Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West, holiday rental in Key West
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West, holiday rental in Key West
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West, holiday rental in Key West

Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Harbour Place 115 in Truman Annex Key West, holiday rental in Key West
Harbour Place 115 in Truman Annex Key West, holiday rental in Key West
Harbour Place 115 in Truman Annex Key West, holiday rental in Key West

Harbour Place 115 in Truman Annex Key West

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Ann Street Cottage: A bright and airy home near Duval Street, holiday rental in Key West
Ann Street Cottage: A bright and airy home near Duval Street, holiday rental in Key West
Ann Street Cottage: A bright and airy home near Duval Street, holiday rental in Key West

Ann Street Cottage: A bright and airy home near Duval Street

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Villa Paradiso: A unique mid-town paradise, holiday rental in Key West
Villa Paradiso: A unique mid-town paradise, holiday rental in Key West
Villa Paradiso: A unique mid-town paradise, holiday rental in Key West

Villa Paradiso: A unique mid-town paradise

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Apple of Your Eye in Paradise (Truman Annex)!, holiday rental in Key West
Apple of Your Eye in Paradise (Truman Annex)!, holiday rental in Key West
Apple of Your Eye in Paradise (Truman Annex)!, holiday rental in Key West

Apple of Your Eye in Paradise (Truman Annex)!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval!, holiday rental in Key West
'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval!, holiday rental in Key West
'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval!, holiday rental in Key West

'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!, holiday rental in Key West
~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!, holiday rental in Key West
~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!, holiday rental in Key West

~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin, holiday rental in Key West
Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin, holiday rental in Key West
Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin, holiday rental in Key West

Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Conch Retreat in Beautiful Truman Annex with 2 Bikes, holiday rental in Key West
Conch Retreat in Beautiful Truman Annex with 2 Bikes, holiday rental in Key West
Conch Retreat in Beautiful Truman Annex with 2 Bikes, holiday rental in Key West

Conch Retreat in Beautiful Truman Annex with 2 Bikes

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Tree House Old Town 2 Bedroom MONTHLY Rental, holiday rental in Key West
The Tree House Old Town 2 Bedroom MONTHLY Rental, holiday rental in Key West
The Tree House Old Town 2 Bedroom MONTHLY Rental, holiday rental in Key West

The Tree House Old Town 2 Bedroom MONTHLY Rental

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West, holiday rental in Key West
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West, holiday rental in Key West
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West, holiday rental in Key West

Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beach House with Ocean View-No Contact Check-In, holiday rental in Key West
Beach House with Ocean View-No Contact Check-In, holiday rental in Key West
Beach House with Ocean View-No Contact Check-In, holiday rental in Key West

Beach House with Ocean View-No Contact Check-In

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard., holiday rental in Key West
BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard., holiday rental in Key West
BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard., holiday rental in Key West

BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful Setting Amongst The Active Island Life Style, holiday rental in Key West
Peaceful Setting Amongst The Active Island Life Style, holiday rental in Key West
Peaceful Setting Amongst The Active Island Life Style, holiday rental in Key West

Peaceful Setting Amongst The Active Island Life Style

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!, holiday rental in Key West
'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!, holiday rental in Key West
'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!, holiday rental in Key West

'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Duval Square Retreat: A beautiful condo steps from the action, holiday rental in Key West
Duval Square Retreat: A beautiful condo steps from the action, holiday rental in Key West
Duval Square Retreat: A beautiful condo steps from the action, holiday rental in Key West

Duval Square Retreat: A beautiful condo steps from the action

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West
Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West
Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West

Henry's Piece Of Paradise On The Ocean In Key West

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Pete's Cottages: Twin Cypress cottages steps from Duval, holiday rental in Key West
Pete's Cottages: Twin Cypress cottages steps from Duval, holiday rental in Key West
Pete's Cottages: Twin Cypress cottages steps from Duval, holiday rental in Key West

Pete's Cottages: Twin Cypress cottages steps from Duval

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Harbor Walk Hideaways, holiday rental in Key West
Harbor Walk Hideaways, holiday rental in Key West
Harbor Walk Hideaways, holiday rental in Key West

Harbor Walk Hideaways

Private Room
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West, holiday rental in Key West
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West, holiday rental in Key West
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West, holiday rental in Key West

Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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2022 IS THE FINAL YEAR.  Giving it to a vacation rental company for 2023., holiday rental in Key West
2022 IS THE FINAL YEAR.  Giving it to a vacation rental company for 2023., holiday rental in Key West
2022 IS THE FINAL YEAR.  Giving it to a vacation rental company for 2023., holiday rental in Key West

2022 IS THE FINAL YEAR. Giving it to a vacation rental company for 2023.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Penthouse Level Ocean Views from every room  Tropical Excellence, holiday rental in Key West
Penthouse Level Ocean Views from every room  Tropical Excellence, holiday rental in Key West
Penthouse Level Ocean Views from every room  Tropical Excellence, holiday rental in Key West

Penthouse Level Ocean Views from every room Tropical Excellence

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Colony Poolside: A charming bungalow near the historic cemetery, holiday rental in Key West
Colony Poolside: A charming bungalow near the historic cemetery, holiday rental in Key West
Colony Poolside: A charming bungalow near the historic cemetery, holiday rental in Key West

Colony Poolside: A charming bungalow near the historic cemetery

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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