Vacation Rentals with Private Pool in Simonton Beach, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Simonton Beach

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485 Best Vacation Rentals with Private Pool in Simonton Beach (Starting from $328)

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
Simonton Beach, Key West, Florida, USA
1.3k from Simonton Beach 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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Tropical Dreaming by AvantStay | 4 BLKS to Beach! Private Pool!
Tropical Dreaming by AvantStay | 4 BLKS to Beach! Private Pool!
House
Key West, FL, 33040, United States
0.1k from Simonton Beach center

AC, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

2 Bedrooms6 Guests
9.6

Exceptional

104 reviews

$1350
Average price / night
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Amelia Home by AvantStay | In Historic Old Town w/ Pool
Amelia Home by AvantStay | In Historic Old Town w/ Pool
House
Key West, FL, 33040, United States
0.1k from Simonton Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, No Smoking

2 Bedrooms6 Guests
9.8

Exceptional

16 reviews

$1201
Average price / night
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**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
House
Key West, FL, 33040, United States
0.2k from Simonton Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$483
Average price / night
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NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
House
Key West, FL, 33040, United States
0.2k from Simonton Beach center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Free Parking, Heater, Internet

5 Bedrooms12 Guests
10.0

Exceptional

149 reviews

$2141
Average price / night
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HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$328
Average price / night
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4-bedroom resort style home in awesome Key West with large pool and private deck
4-bedroom resort style home in awesome Key West with large pool and private deck
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1414
Average price / night
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Valhalla - in Old Town Key West
Valhalla - in Old Town Key West
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

2 Bedrooms4 Guests
New to Booking
$767
Average price / night
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LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!
LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$492
Average price / night
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VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
Villa
Key West, FL, 33040, United States
0.3k from Simonton Beach center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen

5 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$681
Average price / night
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Casa Grande by AvantStay | Dt Key West | Near South Beach w/ Pool
Casa Grande by AvantStay | Dt Key West | Near South Beach w/ Pool
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

5 Bedrooms12 Guests
9.8

Exceptional

86 reviews

$2161
Average price / night
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Escape to Key West @ ROYAL ESCAPE
Escape to Key West @ ROYAL ESCAPE
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

3 Bedrooms10 Guests
9.6

Exceptional

98 reviews

$1270
Average price / night
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ALOHA - Large 1 level 4bd/4ba Monthly Rental
ALOHA - Large 1 level 4bd/4ba Monthly Rental
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

AC, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

4 Bedrooms10 Guests
New to Booking
$503
Average price / night
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Beautiful 3bd/2ba Monthly Rental - ROYAL HAVEN
Beautiful 3bd/2ba Monthly Rental - ROYAL HAVEN
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

3 Bedrooms6 Guests
New to Booking
$339
Average price / night
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INTO THE BLUE~GRAND OPENING RATES! Pristine 4 BR/3.5 BA Home w/Private Pool!
INTO THE BLUE~GRAND OPENING RATES! Pristine 4 BR/3.5 BA Home w/Private Pool!
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

4 Bedrooms8 Guests
New to Booking
$364
Average price / night
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THE GREEN COCONUT ~ Updated 3 BR, 2 Ba Home w/ Parking and Private Pool!
THE GREEN COCONUT ~ Updated 3 BR, 2 Ba Home w/ Parking and Private Pool!
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

3 Bedrooms6 Guests
New to Booking
$404
Average price / night
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**HALFWAY TO HAVANA @ DUVAL** Two Cottages w/ Pool + LAST KEY SERVICES...
**HALFWAY TO HAVANA @ DUVAL** Two Cottages w/ Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

4 Bedrooms8 Guests
New to Booking
$1523
Average price / night
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Hidden away near the Southernmost Point, Louisa's Hideaway is it!
Hidden away near the Southernmost Point, Louisa's Hideaway is it!
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

200 reviews

$1376
Average price / night
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**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

7 Bedrooms16 Guests
10.0

Exceptional

89 reviews

$2676
Average price / night
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**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

5 Bedrooms12 Guests
10.0

Exceptional

49 reviews

$2304
Average price / night
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Louisa House: A comfortable four bedroom vacation hideaway
Louisa House: A comfortable four bedroom vacation hideaway
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

4 Bedrooms10 Guests
9.4

Superb

177 reviews

$1464
Average price / night
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Catherine House: A charming Old Town Key West cottage
Catherine House: A charming Old Town Key West cottage
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

2 Bedrooms4 Guests
9.8

Exceptional

191 reviews

$816
Average price / night
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**LAYOVER in PARADISE @ CASA MARINA** New Home / Pool + LAST KEY SERVICES…
**LAYOVER in PARADISE @ CASA MARINA** New Home / Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

3 Bedrooms8 Guests
New to Booking
$505
Average price / night
Check Availability
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

3 Bedrooms8 Guests
9.8

Exceptional

210 reviews

$1057
Average price / night
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LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

3 Bedrooms8 Guests
9.8

Exceptional

239 reviews

$1282
Average price / night
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**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$458
Average price / night
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Green Goddess - 4 BD/3 BA Amazing 360 Degrees Rooftop Views! RealKeyWest
Green Goddess - 4 BD/3 BA Amazing 360 Degrees Rooftop Views! RealKeyWest
House
Key West, FL, 33040, United States
0.4k from Simonton Beach center

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

4 Bedrooms8 Guests
8.4

Very Good

5 reviews

$559
Average price / night
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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 Simonton Beach.

Where to stay in Simonton Beach? Best neighborhoods & areas

Simonton Beach Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

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

Prices for rentals with a private pool in Simonton Beach vary depending on the property size, location, and travel season. Rates typically start from around $328 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 Simonton Beach also welcome pets. Currently, 30 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 Simonton Beach 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 Simonton Beach 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.