Oceanfront Rentals in Key West Historic District, FL: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Key West Historic District

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1053 Best Oceanfront Rentals in Key West Historic District (Starting from $285)

Courtney's Place Historic Cottages & Inns
Courtney's Place Historic Cottages & Inns
House
Key West Historic District, Key West, Florida, USA
0.2k from Key West Historic District center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Romantic, Pet-friendly, Lodgings

18 Bedrooms72 Guests
8.8

Fabulous

1291 reviews

$738
Average price / night
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Old Town 4 /4.5 house with private pool and 2 poolside cottages + outdoor shower
Old Town 4 /4.5 house with private pool and 2 poolside cottages + outdoor shower
House
Key West, FL, 33040, United States
0.0k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$574
Average price / night
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Elizabeth's Secret - Old Town Key West
Elizabeth's Secret - Old Town Key West
House
Key West, FL, USA
0.3k from Key West Historic District center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$1628
Average price / night
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Truman House - Private Pool Home in the Heart of Old Town Key West!
Truman House - Private Pool Home in the Heart of Old Town Key West!
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
9.4

Superb

9 reviews

$1391
Average price / night
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Key West Villas
Key West Villas
Villa
Key West, FL, USA
0.3k from Key West Historic District center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

9 Bedrooms28 Guests
9.7

Exceptional

379 reviews

$345
Average price / night
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Escape to \"Casa Escondida\"
Escape to \"Casa Escondida\"
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
New to Booking
$474
Average price / night
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The Island Suite at KW Vacation
The Island Suite at KW Vacation
Apartment
Key West, FL, USA
0.3k from Key West Historic District center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom4 Guests
9.6

Exceptional

36 reviews

$395
Average price / night
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QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
8.4

Very Good

10 reviews

$420
Average price / night
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Westwinds Inn
Westwinds Inn
House
Key West, FL, USA
0.4k from Key West Historic District center

B&bs, Accommodations, Pools, Guest houses, Homestays, Romantic, Lodgings, Vacation rentals, Places to stay

27 Bedrooms28 Guests
8.8

Fabulous

732 reviews

$475
Average price / night
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Old Town! Spacious Condo in Historic Home w/Pool!
Old Town! Spacious Condo in Historic Home w/Pool!
Condo
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
9.4

Superb

10 reviews

$316
Average price / night
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New Orleans House - Gay Male Adult Guesthouse
New Orleans House - Gay Male Adult Guesthouse
House
Key West Historic District, Key West, Florida, USA
0.4k from Key West Historic District center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Hot tubs

13 Bedrooms28 Guests
8.8

Fabulous

193 reviews

$575
Average price / night
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Quilted Giraffe - Private Home in Old Town Key West
Quilted Giraffe - Private Home in Old Town Key West
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.8

Exceptional

7 reviews

$814
Average price / night
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La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
Resort
Key West, FL, USA
0.5k from Key West Historic District center

Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay, Accessible hotels

12 Bedrooms31 Guests
8.3

Very Good

54 reviews

$306
Average price / night
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Casa Azul - Private Pool
Casa Azul - Private Pool
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
New to Booking
$382
Average price / night
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Rose Lane Villas
Rose Lane Villas
Villa
Key West, FL, USA
0.5k from Key West Historic District center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

10 Bedrooms26 Guests
8.4

Very Good

299 reviews

$345
Average price / night
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STAINED GLASS SANCTUARY ~ 3 BR/1.5 Ba Home w/ Pool and Parking!
STAINED GLASS SANCTUARY ~ 3 BR/1.5 Ba Home w/ Pool and Parking!
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$370
Average price / night
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Tranquillity Guest House
Tranquillity Guest House
Apartment
Key West, FL, USA
0.6k from Key West Historic District center

Apartments, Cheap, Accommodations, Pools, Serviced apartments, 3-star, Lodgings, Places to stay

16 Bedrooms4 Guests
8.2

Very Good

255 reviews

$514
Average price / night
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Secret Villa I @ Old Town with Private Pool, close to Duval!
Secret Villa I @ Old Town with Private Pool, close to Duval!
Villa
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

175 reviews

$1293
Average price / night
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The Pirates Penthouse by Last Key Realty
The Pirates Penthouse by Last Key Realty
Apartment
Key West, FL, USA
0.7k from Key West Historic District center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
9.3

Superb

3 reviews

$964
Average price / night
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Secret Villa II @ Old Town: with Private Pool, close to Duval!
Secret Villa II @ Old Town: with Private Pool, close to Duval!
Villa
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

157 reviews

$1265
Average price / night
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**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$545
Average price / night
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CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
Cottage
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$374
Average price / night
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LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

223 reviews

$1219
Average price / night
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The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
Condo
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, Patio

2 Bedrooms4 Guests
9.8

Exceptional

238 reviews

$446
Average price / night
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The Hollinsed House \"Victorian Delights\" - Large 1 Bedroom
The Hollinsed House \"Victorian Delights\" - Large 1 Bedroom
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Internet, Kitchen, Microwave, No Smoking, Patio, Pool, TV

1 Bedroom4 Guests
9.8

Exceptional

125 reviews

$333
Average price / night
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Hollinsed House Poolside / King Studio / sleeps 2
Hollinsed House Poolside / King Studio / sleeps 2
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Internet, Kitchen, Microwave, No Smoking, Patio, Pool, TV

1 Bedroom2 Guests
9.6

Exceptional

116 reviews

$300
Average price / night
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ShangriLa Suite / Queen Studio / Sleeps 2
ShangriLa Suite / Queen Studio / Sleeps 2
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Heater, Internet, Kitchen, Microwave, No Smoking, Patio, Pool

1 Bedroom2 Guests
9.2

Superb

69 reviews

$285
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Oceanfront Rentals in Key West Historic District.

Where to stay in Key West Historic District? Best neighborhoods & areas

Stay Near Key West Historic District's Top Attractions

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Key West Historic District Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 1053 verified oceanfront rentals in Key West Historic District. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Key West Historic District vary depending on the property size, exact beachfront location, and season. Rates typically start from around $285 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Key West Historic District offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Key West Historic District welcome pets. Currently, 27 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Key West Historic District often include features designed for a comfortable coastal stay, such as View, Ocean View, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.