Accommodations in Old Town, FL: Compare 10+ Sites & Save

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  4.  Florida
  5.  Key West
  6.  Old Town

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1820 Best Accommodations in Old Town (Starting from $237)

Ecco Domani by AvantStay Gorgeous Home w Pool Balcony in Great Location Month Long Stays Only
Ecco Domani by AvantStay Gorgeous Home w Pool Balcony in Great Location Month Long Stays Only
House
Key West, FL, USA
0.0k from Old Town center

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

3 Bedrooms6 Guests
New to Booking
$310
Average price / night
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PARROTVILLE Townhome in Windward Park by RENT KEY WEST VACATIONS
PARROTVILLE Townhome in Windward Park by RENT KEY WEST VACATIONS
House
Key West, FL, 33040, United States
0.0k from Old Town center

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

2 Bedrooms4 Guests
10.0

Exceptional

63 reviews

$631
Average price / night
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Absolutely Paradise
Absolutely Paradise
House
Key West, FL, USA
0.0k from Old Town center

Pool, Barbecue/Outdoor Cooking, Breakfast, Parking, Air Conditioner, Internet, Wellness Facilities

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$733
Average price / night
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Absolutely Paradise by RENT KEY WEST VACATIONS - Old Town 3Bd/2Ba Townhome
Absolutely Paradise by RENT KEY WEST VACATIONS - Old Town 3Bd/2Ba Townhome
House
Key West, FL, 33040, United States
0.0k from Old Town center

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

3 Bedrooms8 Guests
8.4

Very Good

5 reviews

$1109
Average price / night
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Baya House
Baya House
House
Key West, FL, USA
0.0k from Old Town center

Restaurant, Sports/Activities, Fireplace/Heating, Air Conditioner, Pool, Balcony/Terrace, Security/Safety

2 Bedrooms4 Guests
8.2

Very Good

10 reviews

$355
Average price / night
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**WINDWARD WAVES @ OLD TOWN** Cozy Cottage Near Duval + LAST KEY SERVICES...
**WINDWARD WAVES @ OLD TOWN** Cozy Cottage Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.0k from Old Town center

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

4 Bedrooms6 Guests
New to Booking
$668
Average price / night
Check Availability
Lighthouse South by Brightwild
Lighthouse South by Brightwild
House
Key West, FL, USA
0.0k from Old Town center

Air Conditioner, Pool, Parking, Internet

2 Bedrooms6 Guests
New to Booking
$293
Average price / night
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Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining
Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining
House
Key West, FL, 33040, United States
0.0k from Old Town center

2 Bedrooms4 Guests
New to Booking
$581
Average price / night
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Tumis Time Out by AvantStay Heart Of Old Town w Shared Pool Month Long Stays Only
Tumis Time Out by AvantStay Heart Of Old Town w Shared Pool Month Long Stays Only
House
Key West, FL, USA
0.0k from Old Town center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$322
Average price / night
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**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.0k from Old Town center

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

2 Bedrooms4 Guests
9.8

Exceptional

79 reviews

$706
Average price / night
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Dancing Palms
Dancing Palms
House
Key West, FL, USA
0.0k from Old Town center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

2 Bedrooms4 Guests
8.0

Good

1 reviews

$474
Average price / night
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Breezy Retreat  2bdrm, 2 bath Windward Park,  Pool, close to Duval
Breezy Retreat 2bdrm, 2 bath Windward Park, Pool, close to Duval
House
Key West, FL, 33040, United States
0.0k from Old Town center

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

2 Bedrooms4 Guests
9.8

Exceptional

20 reviews

$910
Average price / night
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New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
House
Key West, FL, USA
0.1k from Old Town center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
7.8

Good

13 reviews

$955
Average price / night
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Location, location, location in the heart of Old Town!
Location, location, location in the heart of Old Town!
House
Key West, FL, 33040, United States
0.0k from Old Town center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$619
Average price / night
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NEW! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking
NEW! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking
House
Key West, FL, USA
0.1k from Old Town center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
5.0

Review score

2 reviews

$959
Average price / night
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The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$366
Average price / night
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Nassau Suite Key West
Nassau Suite Key West
House
Key West, FL, USA
0.1k from Old Town center

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

1 Bedroom4 Guests
5.0

Review score

3 reviews

$329
Average price / night
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ESPERANZA SUITE Monthly Rental close to Duval
ESPERANZA SUITE Monthly Rental close to Duval
House
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Barbecue, Dryer, Hot Tub, Kitchen, Laundry, Microwave, No Smoking, Pool

1 Bedroom4 Guests
New to Booking
$237
Average price / night
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Sea Esta Suite - Duval Square
Sea Esta Suite - Duval Square
Apartment
Key West, FL, USA
0.1k from Old Town center

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

2 Bedrooms6 Guests
New to Booking
$939
Average price / night
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VanGogh Studio | Updated, Old Town, Heated Pool
VanGogh Studio | Updated, Old Town, Heated Pool
Apartment
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Grill

1 Bedroom2 Guests
8.6

Fabulous

41 reviews

$371
Average price / night
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The Conch House Heritage Inn
The Conch House Heritage Inn
Bed & Breakfast
Old Town, Key West, Florida, USA
0.1k from Old Town center

B&bs, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

7 Bedrooms14 Guests
9.1

Superb

31 reviews

$907
Average price / night
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Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Apartment
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Internet, Microwave, No Smoking, TV

1 Bedroom2 Guests
9.8

Exceptional

24 reviews

$399
Average price / night
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DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

4 Bedrooms8 Guests
9.8

Exceptional

18 reviews

$1736
Average price / night
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Newly-Built, Dog-Friendly Home with Shared Pool - Walk to Beach & Dining
Newly-Built, Dog-Friendly Home with Shared Pool - Walk to Beach & Dining
House
Key West, FL, 33040, United States
0.1k from Old Town center

3 Bedrooms6 Guests
New to Booking
$624
Average price / night
Check Availability
Nassau Suite just steps to Duval Tropical oasis  quiet location Downtown
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
House
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Balcony, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

1 Bedroom4 Guests
9.0

Fabulous

251 reviews

$376
Average price / night
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SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

2 Bedrooms6 Guests
10.0

Exceptional

20 reviews

$239
Average price / night
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INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w/ Community Pool!
INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w/ Community Pool!
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$282
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 Accommodations in Old Town.

Where to stay in Old Town? Best neighborhoods & areas

Stay Near Old Town's Top Attractions

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

Old Town Accommodations on the Map

Frequently Asked Questions

You can explore 1820 verified accommodations in Old Town, including hotels, vacation rentals, resorts, and boutique stays. This variety makes it easier to choose the option that best fits your travel style and budget.

Accommodation prices in Old Town vary based on property type, location, and travel dates. Rates typically start from around $237 per night, with higher prices for premium properties and peak travel periods.

Hotels are ideal for convenience and short stays, while vacation rentals offer more space and privacy. Resorts are suitable for all-inclusive experiences, and boutique properties provide a more unique and personalized stay in Old Town.

Yes, Old Town offers many family-friendly options, including large vacation rentals and hotels with suites or connecting rooms. Currently, 40 listings in Old Town are well-suited for families and group travel.

Booking 30 to 60 days in advance is generally recommended for the best availability and pricing. For peak travel seasons or major events in Old Town, booking several months ahead can help secure your preferred property.

Accommodations in Old Town commonly include amenities such as Pool, Internet, and Wellness Facilities. Availability may vary depending on the type of property you choose.

Yes, some accommodations in Old Town focus on sustainable practices such as energy efficiency and reduced environmental impact. You can filter listings to find options that align with your preferences in Old Town.