Vacation Rentals with Pool in Old Town, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Old Town

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1469 Best Vacation Rentals with Pool in Old Town (Starting from $234)

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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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
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A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
House
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.8

Exceptional

103 reviews

$1134
Average price / night
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ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
House
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

91 reviews

$1156
Average price / night
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Duval Sq., Old Town, very walkable, full kitchen, pool, parking, 2 BR/2.5 BA.
Duval Sq., Old Town, very walkable, full kitchen, pool, parking, 2 BR/2.5 BA.
Condo
Key West, FL, 33040, United States
0.1k from Old Town center

AC, Balcony, Dryer, Elevator, Extra Bed, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$234
Average price / night
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ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
House
Key West, FL, 33040, United States
0.1k from Old Town center

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

3 Bedrooms6 Guests
9.8

Exceptional

105 reviews

$1015
Average price / night
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MONTHLY RENTAL on Iconic Duval Street!!
MONTHLY RENTAL on Iconic Duval Street!!
Condo
Key West, FL, 33040, United States
0.1k from Old Town center

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

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$262
Average price / night
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A contemporary island gem that was formerly used as a bottling plant,
A contemporary island gem that was formerly used as a bottling plant,
House
Key West, FL, 33040, United States
0.2k from Old Town center

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

4 Bedrooms8 Guests
9.8

Exceptional

20 reviews

$1230
Average price / night
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HIDDEN OASIS 3 blocks from Duval
HIDDEN OASIS 3 blocks from Duval
Cottage
Key West, FL, 33040, United States
0.2k from Old Town center

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

1 Bedroom4 Guests
9.6

Exceptional

100 reviews

$764
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 with Pool in Old Town.

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Old Town Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1469 verified vacation rentals with a pool in Old Town. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Old Town vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $234 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Old Town offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Old Town welcome pets. Currently, 40 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Old Town often include additional outdoor features such as Pool, Internet, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Old Town offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.