Vacation Rentals with Private Pool in Saint Mary Star of the Sea, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Saint Mary Star of the Sea

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485 Best Vacation Rentals with Private Pool in Saint Mary Star of the Sea (Starting from $267)

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
Saint Mary Star of the Sea, Key West, Florida, USA
0.6k from Saint Mary Star of the Sea 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 VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.0k from Saint Mary Star of the Sea center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
10.0

Exceptional

141 reviews

$2193
Average price / night
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Modern Elegance at Windsor Townhomes #5
Modern Elegance at Windsor Townhomes #5
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms6 Guests
9.6

Exceptional

57 reviews

$1374
Average price / night
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Spacious Townhome on Windsor Lane 3/3.5
Spacious Townhome on Windsor Lane 3/3.5
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms6 Guests
9.8

Exceptional

130 reviews

$1160
Average price / night
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Relax in Style at Windsor Townhomes #4
Relax in Style at Windsor Townhomes #4
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms6 Guests
9.8

Exceptional

60 reviews

$1223
Average price / night
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Windsor Townhomes #6 - Large pool 3B/3.5 bath, 3 blocks to Duval
Windsor Townhomes #6 - Large pool 3B/3.5 bath, 3 blocks to Duval
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms6 Guests
9.8

Exceptional

85 reviews

$1689
Average price / night
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CASA DEL SUR ~ Renovated 2 BR/2Ba Home with Heated Dip Pool!
CASA DEL SUR ~ Renovated 2 BR/2Ba Home with Heated Dip Pool!
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

2 Bedrooms4 Guests
New to Booking
$382
Average price / night
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**THE SOPHISTICATED SANDPIPER @ OLD TOWN** Home & Pool Near Duval + LAST KEY SER
**THE SOPHISTICATED SANDPIPER @ OLD TOWN** Home & Pool Near Duval + LAST KEY SER
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms6 Guests
New to Booking
$1233
Average price / night
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**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms8 Guests
9.8

Exceptional

135 reviews

$1181
Average price / night
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**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

8 Bedrooms16 Guests
10.0

Exceptional

51 reviews

$2380
Average price / night
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**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

4 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$431
Average price / night
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**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

3 Bedrooms8 Guests
10.0

Exceptional

87 reviews

$1199
Average price / night
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Tropical Tranquility - 4BR Luxury Villa In Old Town Key West  w Pool
Tropical Tranquility - 4BR Luxury Villa In Old Town Key West w Pool
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

4 Bedrooms8 Guests
10.0

Exceptional

59 reviews

$1596
Average price / night
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Enjoy Old Town Key West in this Beautifully furnished house
Enjoy Old Town Key West in this Beautifully furnished house
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

4 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$692
Average price / night
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Runaway Bills
Runaway Bills
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

AC, Balcony, Barbecue, Dryer, Extra Bed, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
8.8

Fabulous

3 reviews

$299
Average price / night
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WINDSONG DELIGHT - Cute house on Windsor Ln
WINDSONG DELIGHT - Cute house on Windsor Ln
House
Key West, FL, 33040, United States
0.1k from Saint Mary Star of the Sea center

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

2 Bedrooms4 Guests
New to Booking
$267
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 Saint Mary Star of the Sea 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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~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
Cottage
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1024
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
0.2k from Saint Mary Star of the Sea 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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**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

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

6 Bedrooms12 Guests
10.0

Exceptional

14 reviews

$524
Average price / night
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MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

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

2 Bedrooms6 Guests
9.6

Exceptional

226 reviews

$1133
Average price / night
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Oasis in Old Town - our special home
Oasis in Old Town - our special home
Cottage
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

5 Bedrooms6 Guests
9.6

Exceptional

23 reviews

$267
Average price / night
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HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!
HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

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

2 Bedrooms4 Guests
9.2

Superb

12 reviews

$313
Average price / night
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The Most Perfect Old Town Key West Location for a Retreat!
The Most Perfect Old Town Key West Location for a Retreat!
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

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

4 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$880
Average price / night
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Private Heated Pool-2BR/2BA-OldTown for full Winter Jan 1 -March 31 -Weekly Maid
Private Heated Pool-2BR/2BA-OldTown for full Winter Jan 1 -March 31 -Weekly Maid
House
Key West, FL, 330341, United States
0.2k from Saint Mary Star of the Sea center

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

2 Bedrooms4 Guests
10.0

Exceptional

16 reviews

$706
Average price / night
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CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w/ Pool & Compact Parking!
CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w/ Pool & Compact Parking!
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$550
Average price / night
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**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
House
Key West, FL, 33040, United States
0.2k from Saint Mary Star of the Sea center

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

3 Bedrooms8 Guests
New to Booking
$394
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 Saint Mary Star of the Sea.

Where to stay in Saint Mary Star of the Sea? Best neighborhoods & areas

Saint Mary Star of the Sea Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 485 verified vacation rentals with a private pool in Saint Mary Star of the Sea. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Saint Mary Star of the Sea vary depending on the property size, location, and travel season. Rates typically start from around $267 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 Saint Mary Star of the Sea also welcome pets. Currently, 29 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 Saint Mary Star of the Sea 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 Saint Mary Star of the Sea 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.