Naramata Wineries - Vacation Rentals in Key West Historic District

Amsterdam's Curry Mansion Inn From US $563
         

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8.8 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Old Town Garden Villas From US $258
         

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9.5 (19 Reviews)
House
  • Air Conditioner
  • Pool
  • View
Casa Tranquility by Brightwild From US $277
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Internet
Sunshine Corner From US $244
         

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New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Green Mermaid From US $238
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Child Friendly
Point Break Suites From US $225
         

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7.3 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Mar Y Sol Ocean Front From US $953
         

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10.0 (4 Reviews)
House
  • Parking
  • Pool
  • View

Luxury Places to Stay in Key West Historic District

Over 557+ Luxury Places to Stay in or Near Key West Historic District
6 Bedroom 6 Bath Guesthouse on Duval Street From US $6,002
         

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9.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Sweet Americana by Last Key Realty From US $5,694
         

Custom House Inn All From US $5,686
         

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New
Apartment
  • Security/Safety
  • Child Friendly
The Joyrise House at Solaire Lunara Bay From US $5,186
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Parking Pool Dock - Starboard House From US $5,037
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
New Waterfront Home - Dreamside House From US $4,798
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
BachelorPARTY HQ for 16-Feet to Duval-Pool-Hot tub From US $4,328
         

Top-Rated Vacation Rentals with a Pool in Key West Historic District

Over 392+ Top-Rated Vacation Rentals with a Pool in or Near Key West Historic District
Somewhere on the beach From US $891
         

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10.0 (3 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
ARIA at Azul Mansion Key West From US $252
         

10.0 (3 Reviews)
House
  • Parking
  • Pool
  • View
The Crestwood House - Private Heated Pool & Parking From US $2,969
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Two Duval Street Suites w parking and pool From US $1,658
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Sombrero Reef Light Suite From US $683
         

10.0 (2 Reviews)
House
  • Pool
  • View
  • Security/Safety
Duval Street Suite w kitchen and shared heated pool From US $609
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • View
New The Altair House - Fire Pit Pool & Hot Tub From US $3,668
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
New The Windrose House - Pool & Pets From US $3,012
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Key West Historic District

Over 218+ Pet-Friendly Vacation Rentals in or Near Key West Historic District
Duval Hideaway From US $830
         

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10.0 (2 Reviews)
House
  • Pet Friendly
  • Security/Safety
  • Child Friendly
Duval Delight From US $535
         

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10.0 (2 Reviews)
House
  • Pet Friendly
  • View
  • Security/Safety
Egret Suite - Southernmost Sanctuary From US $370
         

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10.0 (2 Reviews)
House
  • Pet Friendly
  • Security/Safety
  • Child Friendly
Mastway House -Pool & Dock! From US $2,236
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spindrift House -Huge Pool, Dock From US $2,129
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterlane House -Pool & Boat Dock From US $2,108
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
NEW Private Pool & Docking - Floralee House From US $1,896
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Duke of Catherine by Last Key Realty From US $1,747
         

Large Vacation Homes & Villas in Key West Historic District

Over 89+ Large Vacation Homes & Villas in or Near Key West Historic District
Harbor House Suite A From US $2,693
         

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10.0 (3 Reviews)
House
  • Security/Safety
  • Child Friendly
  • Internet
Spacious 52 ft Catamaran for Dockside Stay From US $1,259
         

10.0 (1 Review)
Boat Rental
  • Pool
  • View
  • Ocean View
Key West Villas From US $369
         

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9.7 (379 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Evershore House -Pool, Parking, Dock! From US $2,275
         

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9.6 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Aquaria House -Pool & Boat Dock From US $2,144
         

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9.6 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Harbor House Penthouse- B From US $1,964
         

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9.5 (6 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Marreros Guest Mansion - Adult Only From US $292
         

9.4 (136 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Pool
  • Designated Smoking Area
Andrews Inn & Garden Cottages From US $437
         

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9.4 (132 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Key West Historic District

Over 42+ Wheelchair Accessible Vacation Homes in or Near Key West Historic District
Chic 2 Bedroom Condo 300 Steps from Duval St From US $276
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
H2O Suites- Adults Only From US $1,688
         

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9.5 (508 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Santa Maria Suites Resort From US $476
         

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9.3 (681 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Key West Harbor Inn - Adults Only From US $320
         

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9.2 (261 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Pool
  • View
Courtney's Place Historic Cottages & Inns From US $738
         

9.0 (1175 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Westwinds Inn From US $292
         

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8.6 (637 Reviews)
House
  • Air Conditioner
  • Pool
  • Designated Smoking Area
Oceans Edge Key West From US $276
         

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8.5 (1206 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Hyatt Centric Key West Resort & Spa From US $387
         

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8.5 (503 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly

Key West Historic District Vacation Rentals and Airbnb Places to Stay Under $200

Over 19+ Key West Historic District Vacation Rentals and Airbnb Places to Stay Under $200
Ibis by AvantStay From US $190
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
L'Habitation Guesthouse- Adult Exclusive From US $199
         

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9.0 (1414 Reviews)
Bed & Breakfast
  • Air Conditioner
  • View
  • Balcony/Terrace
DoubleTree by Hilton Grand Key Resort From US $196
         

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8.0 (600 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Resort chic on the water! From US $172
         

6.3 (12 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • Pool
Great location 1/2 block from Duval St - No parking From US $200
         

New
Apartment
  • Air Conditioner
  • Child Friendly
  • Internet
Andy's Attic From US $199
         

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New
House
  • Pet Friendly
  • View
  • Security/Safety
Lazy Gecko by AvantStay From US $198
         

Coral Breeze by AvantStay From US $185
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Pool

About Key West Historic District Vacation Rentals

With more than 566 Key West Historic District vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Naramatawineries and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Key West Historic District.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Naramatawineries Key West Historic District, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Key West Historic District. Places to stay near Key West Historic District are 991.34 ft² on average, with prices averaging US $873 a night.

Naramatawineries makes it easy and safe to find and compare vacation rentals in Key West Historic District with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Key West Historic District

Type Count
Vacation Homes 333
Holiday Apartments 132
Hotels 54
B&B 19
Resorts 16
Villas 4
Hostels 1

Use these Quick Filters to Find a Vacation Rental in Key West Historic District

Pro Tip: Naramatawineries makes it easy to compare the best listings on Naramatawineries homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Naramatawineries homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Key West Historic District.

Weather in Key West Historic District

View the weather forecast for Key West Historic District before booking your Key West Historic District Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Key West Historic District Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Key West Historic District?

There are a lot of options in Key West Historic District. If you plan on staying in the Key West Historic District area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Key West Historic District:

Which vacation homes in Key West Historic District are best for families?

If you are looking for a family-friendly vacation home in Key West Historic District, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Key West Historic District:

How many vacation rentals are available in Key West Historic District?

Currently, the total number of properties listed in 2026 is over 566 in the Key West Historic District area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Key West Historic District.