Vacation Rentals with Private Pool in Flagler Station Oversea Railway Historeum, FL: Compare 10+ Sites & Save

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  3.  USA

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  5.  Key West
  6.  Flagler Station Oversea Railway Historeum

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485 Best Vacation Rentals with Private Pool in Flagler Station Oversea Railway Historeum (Starting from $243)

Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
House
Flagler Station Oversea Railway Historeum, Key West, Florida, USA
0.4k from Flagler Station Oversea Railway Historeum center

Pool, Private Pool, Kitchen, Parking, Internet, Air Conditioner, Child Friendly

1 Bedroom4 Guests
New to Booking
$348
Average price / night
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CASA MARGARITA Steps to the Historic Seaport
CASA MARGARITA Steps to the Historic Seaport
House
Key West, FL, 33040, United States
0.1k from Flagler Station Oversea Railway Historeum center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
9.8

Exceptional

127 reviews

$1413
Average price / night
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Paradise on Eaton- 3 bedroom 3 bath home w/private pool near Historic Seaport
Paradise on Eaton- 3 bedroom 3 bath home w/private pool near Historic Seaport
House
Key West, FL, 33040, United States
0.1k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms6 Guests
9.0

Fabulous

9 reviews

$243
Average price / night
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Quaint Key West Getaway: Historic Knowles House w/Private Pool & Rooftop Deck
Quaint Key West Getaway: Historic Knowles House w/Private Pool & Rooftop Deck
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

7 Bedrooms16 Guests
10.0

Exceptional

3 reviews

$2874
Average price / night
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MONTHLY LISTING! Seacret Paradise: Desirable Oasis in the Heart of Old Town
MONTHLY LISTING! Seacret Paradise: Desirable Oasis in the Heart of Old Town
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$774
Average price / night
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**THE WICKED TUNA @ THE SEAPORT** Private Home & Pool + LAST KEY SERVICES…
**THE WICKED TUNA @ THE SEAPORT** Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms6 Guests
New to Booking
$409
Average price / night
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Charming 4-bedroom house with pool - 10 MIN. WALK TO DUVAL STREET
Charming 4-bedroom house with pool - 10 MIN. WALK TO DUVAL STREET
House
Key west, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

4 Bedrooms8 Guests
New to Booking
$856
Average price / night
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New Property - Belle of Key West! Old Town 29 nt min.
New Property - Belle of Key West! Old Town 29 nt min.
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

4 Bedrooms8 Guests
New to Booking
$623
Average price / night
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THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms6 Guests
9.8

Exceptional

22 reviews

$482
Average price / night
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Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.8

Exceptional

56 reviews

$399
Average price / night
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**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$571
Average price / night
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Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$399
Average price / night
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Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$532
Average price / night
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The Gideon Lowe House - Old Town Key West
The Gideon Lowe House - Old Town Key West
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$785
Average price / night
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Key West Premium Location - Luxury 4BR/4BA – Private Pool by Historic Seaport
Key West Premium Location - Luxury 4BR/4BA – Private Pool by Historic Seaport
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

AC, Balcony, Barbecue, Dryer, Extra Bed, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$952
Average price / night
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**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…
**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

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

3 Bedrooms6 Guests
New to Booking
$1477
Average price / night
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Kemp House - in the Historic Seaport Area Key West
Kemp House - in the Historic Seaport Area Key West
House
Key West, FL, 33040, United States
0.2k from Flagler Station Oversea Railway Historeum center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$1122
Average price / night
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PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.8

Exceptional

37 reviews

$2591
Average price / night
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**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

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

6 Bedrooms12 Guests
10.0

Exceptional

91 reviews

$3128
Average price / night
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Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Cottage
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

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

2 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$513
Average price / night
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The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

AC, Dryer, Hot Tub, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms10 Guests
9.8

Exceptional

22 reviews

$1816
Average price / night
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Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16
Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

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

7 Bedrooms16 Guests
9.4

Superb

40 reviews

$2637
Average price / night
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SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

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

5 Bedrooms10 Guests
9.8

Exceptional

206 reviews

$2516
Average price / night
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~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.
~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

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

4 Bedrooms8 Guests
9.4

Superb

24 reviews

$540
Average price / night
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STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

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

8 Bedrooms20 Guests
9.6

Exceptional

76 reviews

$2867
Average price / night
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BLUE ROOSTER ~ Spectacular 4 Bed/4 Bath with Pool and Solarium in Old Town!
BLUE ROOSTER ~ Spectacular 4 Bed/4 Bath with Pool and Solarium in Old Town!
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

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

4 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$788
Average price / night
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Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
House
Key West, FL, 33040, United States
0.3k from Flagler Station Oversea Railway Historeum center

AC, Balcony, Barbecue, Dryer, Hot Tub, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
New to Booking
$717
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 Private Pool in Flagler Station Oversea Railway Historeum.

Where to stay in Flagler Station Oversea Railway Historeum? Best neighborhoods & areas

Flagler Station Oversea Railway Historeum Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 485 verified vacation rentals with a private pool in Flagler Station Oversea Railway Historeum. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Flagler Station Oversea Railway Historeum vary depending on the property size, location, and travel season. Rates typically start from around $243 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Flagler Station Oversea Railway Historeum also welcome pets. Currently, 22 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Flagler Station Oversea Railway Historeum often include additional features such as Pool, Private Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Flagler Station Oversea Railway Historeum include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.