Vacation Rentals with Private Pool in Whispering Pines, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Big Pine Key
  6.  Whispering Pines

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81 Best Vacation Rentals with Private Pool in Whispering Pines (Starting from $216)

Mickey and Lynn's House of Windows
Mickey and Lynn's House of Windows
House
Big Pine Key, FL, 33050, United States
0.1k from Whispering Pines center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms7 Guests
10.0

Exceptional

8 reviews

$403
Average price / night
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3 BR Canal Home in Big Pine Key, FL - Private Pool/Spa - Great Boating Access!!!
3 BR Canal Home in Big Pine Key, FL - Private Pool/Spa - Great Boating Access!!!
House
Big Pine Key, FL, 33043, United States
0.4k from Whispering Pines center

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

3 Bedrooms6 Guests
New to Booking
$259
Average price / night
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Family friendly canal home,150 ft dock, easy access to Atl & Gulf
Family friendly canal home,150 ft dock, easy access to Atl & Gulf
House
Big Pine Key, FL, 33043, United States
0.4k from Whispering Pines center

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

5 Bedrooms13 Guests
10.0

Exceptional

1 reviews

$538
Average price / night
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A Serene Florida Escape in Big Pine Key 3 bed 2 bath house, pool, dock, sleep 8
A Serene Florida Escape in Big Pine Key 3 bed 2 bath house, pool, dock, sleep 8
House
Big Pine Key, FL, 33043, United States
1.4k from Whispering Pines center

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

3 Bedrooms8 Guests
New to Booking
$410
Average price / night
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Upscale ocean front home & easy canal boat access to Gulf or Atlantic
Upscale ocean front home & easy canal boat access to Gulf or Atlantic
House
Big Pine Key, FL, 33043, United States
1.5k from Whispering Pines center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$293
Average price / night
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🐠 HEATED SWIM SPA / OPEN WATER VIEWS / BOAT DOCK / LUXURIOUS /  BUILT IN 2023🐬
🐠 HEATED SWIM SPA / OPEN WATER VIEWS / BOAT DOCK / LUXURIOUS / BUILT IN 2023🐬
House
Big Pine Key, FL, 33043, United States
1.5k from Whispering Pines center

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

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$464
Average price / night
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POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
House
Big Pine Key, FL, 33043, United States
1.6k from Whispering Pines center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$451
Average price / night
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Amazing Pool & Canal Ground Level Home, Ocean access
Amazing Pool & Canal Ground Level Home, Ocean access
House
Big Pine Key, FL, 33043, United States
1.6k from Whispering Pines center

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

3 Bedrooms6 Guests
9.6

Exceptional

23 reviews

$534
Average price / night
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SEA FOREVER! Gorgeous Ocean-Front Paradise!
SEA FOREVER! Gorgeous Ocean-Front Paradise!
House
Big Pine Key, FL, 33043, United States
1.6k from Whispering Pines center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Internet, Kitchen

5 Bedrooms12 Guests
New to Booking
$574
Average price / night
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Sea-Esta: 3BR Canal-Front Escape on Big Pine Key, Pool, Dockage & Quick Access to Gulf & Atlantic
Sea-Esta: 3BR Canal-Front Escape on Big Pine Key, Pool, Dockage & Quick Access to Gulf & Atlantic
House
Big Pine Key, FL, 33043, United States
1.8k from Whispering Pines center

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

3 Bedrooms8 Guests
8.8

Fabulous

3 reviews

$359
Average price / night
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Island Sunrise Resort- 3 acre estate with open water sunrises.
Island Sunrise Resort- 3 acre estate with open water sunrises.
House
big pine key, FL, 33043, United States
2.0k from Whispering Pines center

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

3 Bedrooms8 Guests
10.0

Exceptional

64 reviews

$605
Average price / night
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Fishermen's Paradise | Pool, dock, gorgeous home
Fishermen's Paradise | Pool, dock, gorgeous home
House
Big Pine Key, FL, 33043, United States
2.0k from Whispering Pines center

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

3 Bedrooms8 Guests
9.8

Exceptional

28 reviews

$1194
Average price / night
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Big Pine Latitude Adjustment
Big Pine Latitude Adjustment
House
Big Pine Key, FL, 33043, United States
2.0k from Whispering Pines center

AC, Balcony, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms10 Guests
New to Booking
$464
Average price / night
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Modern multi story waterfront home, 30 minutes from Key west.
Modern multi story waterfront home, 30 minutes from Key west.
House
Big Pine Key, FL, 33043, United States
2.0k from Whispering Pines center

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

4 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$460
Average price / night
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Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage!
Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage!
House
Big Pine Key, FL, 33043, United States
2.1k from Whispering Pines center

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

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$612
Average price / night
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Big Pine Key, Double Wide Canal w/ Super Quick Direct Access to Gulf & Atlantic
Big Pine Key, Double Wide Canal w/ Super Quick Direct Access to Gulf & Atlantic
House
Big Pine Key, FL, 33043, United States
2.2k from Whispering Pines center

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

3 Bedrooms6 Guests
9.6

Exceptional

13 reviews

$319
Average price / night
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Canal Front Home With Pool And Hot Tub
Canal Front Home With Pool And Hot Tub
House
Big Pine Key, FL, 33043, United States
2.4k from Whispering Pines center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$277
Average price / night
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Manatee Watch | 5 bedrooms, pool, ocean access
Manatee Watch | 5 bedrooms, pool, ocean access
House
Big Pine Key, FL, 33043, United States
2.4k from Whispering Pines center

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

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$574
Average price / night
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Slice of Paradise: Captivating Open Water Views, Deep Canal, Dockage, Heated Pool, and Pet-Friendly!
Slice of Paradise: Captivating Open Water Views, Deep Canal, Dockage, Heated Pool, and Pet-Friendly!
House
Big Pine Key, FL, 33043, United States
2.4k from Whispering Pines center

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

3 Bedrooms8 Guests
9.2

Superb

5 reviews

$348
Average price / night
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Awesome Open Water View at Blue Heron Estate
Awesome Open Water View at Blue Heron Estate
House
Big Pine Key, FL, 33043, United States
2.5k from Whispering Pines center

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

4 Bedrooms9 Guests
10.0

Exceptional

63 reviews

$851
Average price / night
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Lower Keys Retreat.....  Come....  Relax in Paradise!!
Lower Keys Retreat..... Come.... Relax in Paradise!!
House
Big Pine Key, FL, 33043, United States
2.6k from Whispering Pines center

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

3 Bedrooms8 Guests
9.8

Exceptional

17 reviews

$337
Average price / night
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Secluded Tropical Retreat: 60' Dock, Large Pool, World-Class Fishing & Lobster
Secluded Tropical Retreat: 60' Dock, Large Pool, World-Class Fishing & Lobster
House
Big Pine Key, FL, 33043, United States
2.7k from Whispering Pines center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$416
Average price / night
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Big Pine Paradise: Beautiful Updated 4BR Canal Front Home, Pool, Dockage, Easy Gulf/Atlantic Access
Big Pine Paradise: Beautiful Updated 4BR Canal Front Home, Pool, Dockage, Easy Gulf/Atlantic Access
House
Big Pine Key, FL, 33043, United States
2.7k from Whispering Pines center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$318
Average price / night
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SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
House
Big Pine Key, FL, 33043, United States
2.7k from Whispering Pines center

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

2 Bedrooms6 Guests
10.0

Exceptional

23 reviews

$258
Average price / night
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Waterfront Pool Home! - Heavenly Hideout - Big Pine Key
Waterfront Pool Home! - Heavenly Hideout - Big Pine Key
House
Big Pine Key, FL, 33043, United States
2.7k from Whispering Pines center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$229
Average price / night
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Paradise Retreat ~ BPK
Paradise Retreat ~ BPK
House
Big Pine Key, FL, 33043, United States
3.0k from Whispering Pines center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$216
Average price / night
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Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
House
Big Pine Key, FL, 33043, United States
3.4k from Whispering Pines center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$575
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 Whispering Pines.

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Whispering Pines Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 81 verified vacation rentals with a private pool in Whispering Pines. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Whispering Pines vary depending on the property size, location, and travel season. Rates typically start from around $216 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 Whispering Pines 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 Whispering Pines often include additional features such as Kitchen, Laundry, and Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Whispering Pines 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.