Vacation Rentals in Downtown, FL: Compare 10+ Sites & Save

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  4.  Florida
  5.  Key West
  6.  Downtown

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1736 Best Vacation Rentals in Downtown (Starting from $142)

Mayas Secret Treasure by Last Key Realty
Mayas Secret Treasure by Last Key Realty
Apartment
Key West, FL, USA
0.0k from Downtown center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$1236
Average price / night
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No secrets at Pilar's Secret - Just a great location!
No secrets at Pilar's Secret - Just a great location!
House
Key West, FL, 33040, United States
0.0k from Downtown center

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

3 Bedrooms8 Guests
9.8

Exceptional

116 reviews

$1487
Average price / night
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Endless Summer by Last Key Realty
Endless Summer by Last Key Realty
House
Key West, FL, USA
0.0k from Downtown center

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

5 Bedrooms12 Guests
New to Booking
$1602
Average price / night
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**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.0k from Downtown center

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

16 Bedrooms32 Guests
10.0

Exceptional

5 reviews

$4416
Average price / night
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All Together Now by Last Key Realty
All Together Now by Last Key Realty
House
Key West, FL, USA
0.0k from Downtown center

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

13 Bedrooms32 Guests
New to Booking
$3887
Average price / night
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Sky Suite with Balcony Overlooking Duval Street
Sky Suite with Balcony Overlooking Duval Street
Apartment
Key West, FL, 33040, United States
0.0k from Downtown center

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

2 Bedrooms6 Guests
9.6

Exceptional

48 reviews

$929
Average price / night
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Sky Suite On Duval
Sky Suite On Duval
Apartment
Key West, FL, USA
0.0k from Downtown center

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

2 Bedrooms6 Guests
9.3

Superb

8 reviews

$1183
Average price / night
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Cloud Suite on Duval Street with Balcony
Cloud Suite on Duval Street with Balcony
Apartment
Key West, FL, 33040, United States
0.0k from Downtown center

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

2 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$908
Average price / night
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Cloud Suite On Duval
Cloud Suite On Duval
Apartment
Key West, FL, USA
0.0k from Downtown center

Apartments, Cheap, Accommodations, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals

2 Bedrooms6 Guests
9.3

Superb

12 reviews

$979
Average price / night
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Sky Suites Retreat - Balcony Overlooking Duval
Sky Suites Retreat - Balcony Overlooking Duval
Apartment
Key West, FL, 33040, United States
0.0k from Downtown center

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

4 Bedrooms12 Guests
10.0

Exceptional

18 reviews

$1911
Average price / night
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Great location 1/2 block from Duval St - No parking
Great location 1/2 block from Duval St - No parking
Apartment
Key West, FL, USA
0.1k from Downtown center

Internet, Air Conditioner, Child Friendly

1 Bedroom2 Guests
New to Booking
$200
Average price / night
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One Bedroom Deck Villa Steps from Duval!
One Bedroom Deck Villa Steps from Duval!
Villa
Key West, FL, 33040, United States
0.0k from Downtown center

AC, Breakfast Included, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
10.0

Exceptional

10 reviews

$632
Average price / night
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Rooftop Penthouse
Rooftop Penthouse
House
Key West, FL, USA
0.1k from Downtown center

Internet, Laundry, Security/Safety, Child Friendly

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$661
Average price / night
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The Perch on Duval- Hip & Modern Duval Suite
The Perch on Duval- Hip & Modern Duval Suite
Apartment
Key West, FL, 33040, United States
0.1k from Downtown center

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

2 Bedrooms5 Guests
9.8

Exceptional

15 reviews

$772
Average price / night
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Peak Of Duval
Peak Of Duval
House
Key West, FL, USA
0.1k from Downtown center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$421
Average price / night
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Lofted 1 bedroom suite right off Duval St
Lofted 1 bedroom suite right off Duval St
Apartment
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Kitchen, Microwave, No Smoking, Patio

1 Bedroom4 Guests
9.6

Exceptional

68 reviews

$336
Average price / night
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Americana Tropicale by Last Key Realty
Americana Tropicale by Last Key Realty
House
Key West, FL, USA
0.1k from Downtown center

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

4 Bedrooms10 Guests
New to Booking
$2020
Average price / night
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Casa Loca - so close to Duval 3bd/2ba private home
Casa Loca - so close to Duval 3bd/2ba private home
House
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Barbecue, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms8 Guests
9.8

Exceptional

149 reviews

$1191
Average price / night
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Conch Cove
Conch Cove
House
Key West, FL, USA
0.1k from Downtown center

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

3 Bedrooms8 Guests
New to Booking
$1428
Average price / night
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Deckside Suite - Efficiency at its finest!
Deckside Suite - Efficiency at its finest!
Apartment
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Internet, Kitchen, Microwave, No Smoking, TV

1 Bedroom2 Guests
9.0

Fabulous

78 reviews

$305
Average price / night
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Villa Angelita by Last Key Realty
Villa Angelita by Last Key Realty
House
Key West, FL, USA
0.1k from Downtown center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$1547
Average price / night
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Rent at PORCHSIDE PARADISE - Steps to Duval
Rent at PORCHSIDE PARADISE - Steps to Duval
Apartment
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio, TV

1 Bedroom4 Guests
9.0

Fabulous

77 reviews

$401
Average price / night
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Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
Villa
Key West, FL, 33040, United States
0.1k from Downtown center

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

3 Bedrooms7 Guests
New to Booking
$1047
Average price / night
Check Availability
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Apartment
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Internet, No Smoking, TV

1 Bedroom2 Guests
9.8

Exceptional

32 reviews

$409
Average price / night
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Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Apartment
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Internet, Kitchen, Microwave, No Smoking, TV

1 Bedroom2 Guests
9.8

Exceptional

28 reviews

$399
Average price / night
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Shipwreck Suite - Apartment on Duval St, Key West!
Shipwreck Suite - Apartment on Duval St, Key West!
Apartment
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Balcony, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool, TV

1 Bedroom6 Guests
10.0

Exceptional

2 reviews

$142
Average price / night
Check Availability
Casa Mamisa - 2 bedroom home in Old Town
Casa Mamisa - 2 bedroom home in Old Town
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

2 Bedrooms6 Guests
9.4

Superb

3 reviews

$162
Average price / night
Check Availability

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 Vacation Rentals in Downtown.

Where to stay in Downtown? Best neighborhoods & areas

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VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Downtown Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1736 verified vacation rentals in Downtown. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Downtown vary depending on the season, property size, and location. Rates typically start from around $142 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Downtown include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Downtown welcome pets. Currently, 46 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Downtown often include amenities such as Internet, Wellness Facilities, and Kitchen. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.