Vacation Rentals with Private Pool in Studios of Key West, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Studios of Key West

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485 Best Vacation Rentals with Private Pool in Studios of Key West (Starting from $203)

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
Studios of Key West, Key West, Florida, USA
0.4k from Studios of Key West 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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Anchor's Away - Private Pool Home in Old Town Key West!
Anchor's Away - Private Pool Home in Old Town Key West!
House
Key West, FL, 33040, United States
0.0k from Studios of Key West center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$203
Average price / night
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Ashe St Serenade: 3BD/3.5BA Luxury Retreat, Private Pool in an Island Oasis.
Ashe St Serenade: 3BD/3.5BA Luxury Retreat, Private Pool in an Island Oasis.
House
Key West, FL, 33040, United States
0.0k from Studios of Key West center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$480
Average price / night
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A Bit of Heaven is the perfect monthly rental in Key West
A Bit of Heaven is the perfect monthly rental in Key West
House
Key West, FL, 33040, United States
0.1k from Studios of Key West center

AC, Barbecue, Dryer, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Pool

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$351
Average price / night
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Sun, Sea, & Citrus - Bright 2-Bedroom Monthly Rental in Old Town Key West with Private Pool. Sleeps 5-6
Sun, Sea, & Citrus - Bright 2-Bedroom Monthly Rental in Old Town Key West with Private Pool. Sleeps 5-6
Condo
Key West, FL, 33040, United States
0.1k from Studios of Key West center

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

2 Bedrooms5 Guests
New to Booking
$283
Average price / night
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**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
House
Key West, FL, 33040, United States
0.1k from Studios of Key West center

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

3 Bedrooms6 Guests
10.0

Exceptional

87 reviews

$1205
Average price / night
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SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
House
Key West, FL, 33040, United States
0.1k from Studios of Key West center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$810
Average price / night
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~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.
~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.
House
Key West, FL, 33040, United States
0.1k from Studios of Key West center

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

3 Bedrooms6 Guests
9.8

Exceptional

189 reviews

$1159
Average price / night
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PURA VIDA ~ 3 Bed/3.5 Bath Home on Quaint Old Town Lane!
PURA VIDA ~ 3 Bed/3.5 Bath Home on Quaint Old Town Lane!
House
Key West, FL, 33040, United States
0.1k from Studios of Key West center

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

3 Bedrooms6 Guests
9.6

Exceptional

7 reviews

$452
Average price / night
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~ VILLA AZUL ~ Enjoy this historic home with pool house and parking.
~ VILLA AZUL ~ Enjoy this historic home with pool house and parking.
House
Key West, FL, 33040, United States
0.1k from Studios of Key West center

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

3 Bedrooms6 Guests
9.4

Superb

21 reviews

$347
Average price / night
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~ASHE HOUSE~ Renovated and relaxing with pool, porches, and privacy!
~ASHE HOUSE~ Renovated and relaxing with pool, porches, and privacy!
House
Key West, FL, 33040, United States
0.1k from Studios of Key West center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$452
Average price / night
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Paradise on White Street
Paradise on White Street
House
Key West, FL, 33040, United States
0.1k from Studios of Key West center

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

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$493
Average price / night
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BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!
House
Key West, FL, 33040, United States
0.1k from Studios of Key West center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$517
Average price / night
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Meadows Manor | Elegant Oasis with Private Pool
Meadows Manor | Elegant Oasis with Private Pool
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

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

4 Bedrooms8 Guests
9.4

Superb

14 reviews

$2369
Average price / night
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LONE PALM COTTAGE ~ 3 BR, 2.5 Ba Home w/ 2 Cottages, Pool & Parking!
LONE PALM COTTAGE ~ 3 BR, 2.5 Ba Home w/ 2 Cottages, Pool & Parking!
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$361
Average price / night
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** FLIGHT OF THE FLAMINGO @ OLD TOWN ** Home & Private Pool + LAST KEY SERVICES.
** FLIGHT OF THE FLAMINGO @ OLD TOWN ** Home & Private Pool + LAST KEY SERVICES.
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

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

3 Bedrooms5 Guests
New to Booking
$489
Average price / night
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**BOHEMIA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...
**BOHEMIA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

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

3 Bedrooms8 Guests
New to Booking
$655
Average price / night
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**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

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

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$407
Average price / night
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CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

AC, Barbecue, Dryer, Extra Bed, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.8

Exceptional

231 reviews

$1082
Average price / night
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WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w/ Pool!
WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w/ Pool!
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

AC, Barbecue, Dryer, Extra Bed, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms9 Guests
9.4

Superb

6 reviews

$448
Average price / night
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OLD TOWN GEM in SEPT26! Private pool, stunning decor, 5-star reviews. NO PETS
OLD TOWN GEM in SEPT26! Private pool, stunning decor, 5-star reviews. NO PETS
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

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

2 Bedrooms4 Guests
10.0

Exceptional

4 reviews

$737
Average price / night
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**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE
**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

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

4 Bedrooms9 Guests
New to Booking
$596
Average price / night
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**ANGELA’S ECLECTIC GALLERY @ SOLARIS HILL** Exceptional Home & Pool + LAST KEY
**ANGELA’S ECLECTIC GALLERY @ SOLARIS HILL** Exceptional Home & Pool + LAST KEY
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

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

3 Bedrooms6 Guests
New to Booking
$506
Average price / night
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Charming + Circa 1889 Historic Eyebrow Home
Charming + Circa 1889 Historic Eyebrow Home
House
Key West, FL, 33040, United States
0.2k from Studios of Key West center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, No Smoking, Pool

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$262
Average price / night
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**THE ARTIST’S AVIARY @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVIC
**THE ARTIST’S AVIARY @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVIC
House
Key West, FL, 33040, United States
0.3k from Studios of Key West center

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

3 Bedrooms6 Guests
New to Booking
$419
Average price / night
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Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
House
Key West, FL, 33040, United States
0.3k from Studios of Key West center

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

4 Bedrooms10 Guests
New to Booking
$613
Average price / night
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Pineapple Conch House - 2 BR Old Town Pool Home
Pineapple Conch House - 2 BR Old Town Pool Home
House
Key West, FL, 33040, United States
0.3k from Studios of Key West center

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

2 Bedrooms4 Guests
New to Booking
$242
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 Studios of Key West.

Where to stay in Studios of Key West? Best neighborhoods & areas

Studios of Key West Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

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

Prices for rentals with a private pool in Studios of Key West vary depending on the property size, location, and travel season. Rates typically start from around $203 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 Studios of Key West also welcome pets. Currently, 31 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 Studios of Key West 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 Studios of Key West 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.