Vacation Rentals with Private Pool in Port Pine Heights, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Big Pine Key
  6.  Port Pine Heights

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80 Best Vacation Rentals with Private Pool in Port Pine Heights (Starting from $184)

Secluded Hideaway with private pool and canal
Secluded Hideaway with private pool and canal
House
Big Pine Key, FL, 33043, United States
0.2k from Port Pine Heights center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, No Smoking, Pool, TV

3 Bedrooms6 Guests
New to Booking
$184
Average price / night
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The most setup home in BPK TIKI HUT,POOL ,GRILL ,CANAL FRONT, FREE UNLIMITED ICE
The most setup home in BPK TIKI HUT,POOL ,GRILL ,CANAL FRONT, FREE UNLIMITED ICE
House
Gordon road, FL, 33043, United States
0.6k from Port Pine Heights center

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

4 Bedrooms12 Guests
9.2

Superb

5 reviews

$382
Average price / night
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Hibiscus House - Heated Pool
Hibiscus House - Heated Pool
House
Big Pine Key, FL, 33043, United States
2.9k from Port Pine Heights center

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

4 Bedrooms10 Guests
New to Booking
$287
Average price / night
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Paradise Retreat ~ BPK
Paradise Retreat ~ BPK
House
Big Pine Key, FL, 33043, United States
3.5k from Port Pine Heights 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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Waterfront Pool Home! - Heavenly Hideout - Big Pine Key
Waterfront Pool Home! - Heavenly Hideout - Big Pine Key
House
Big Pine Key, FL, 33043, United States
4.0k from Port Pine Heights 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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Great Location , Great Vibes, Great Pool
Great Location , Great Vibes, Great Pool
House
Summerland Key, FL, 33042, United States
4.1k from Port Pine Heights center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms14 Guests
9.6

Exceptional

5 reviews

$563
Average price / night
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Frigate's Nest extraordinary 8bed/8bath nightly rental with dockage & private pool
Frigate's Nest extraordinary 8bed/8bath nightly rental with dockage & private pool
House
Little Torch Key, FL, 33042, United States
4.4k from Port Pine Heights center

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

8 Bedrooms16 Guests
8.0

Good

4 reviews

$2218
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
4.5k from Port Pine Heights 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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Lower Keys Retreat.....  Come....  Relax in Paradise!!
Lower Keys Retreat..... Come.... Relax in Paradise!!
House
Big Pine Key, FL, 33043, United States
4.5k from Port Pine Heights 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
4.6k from Port Pine Heights 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
4.8k from Port Pine Heights 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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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
4.9k from Port Pine Heights 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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Amazing Pool & Canal Ground Level Home, Ocean access
Amazing Pool & Canal Ground Level Home, Ocean access
House
Big Pine Key, FL, 33043, United States
5.0k from Port Pine Heights 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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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
5.1k from Port Pine Heights 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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Canal Front Home With Pool And Hot Tub
Canal Front Home With Pool And Hot Tub
House
Big Pine Key, FL, 33043, United States
5.1k from Port Pine Heights 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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SEA FOREVER! Gorgeous Ocean-Front Paradise!
SEA FOREVER! Gorgeous Ocean-Front Paradise!
House
Big Pine Key, FL, 33043, United States
5.1k from Port Pine Heights 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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Very Private 3 Bedroom / 2 Bath Canal Home in Little Torch Key w/ Private Pool
Very Private 3 Bedroom / 2 Bath Canal Home in Little Torch Key w/ Private Pool
House
Little Torch Key, FL, 33042, United States
5.3k from Port Pine Heights center

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

3 Bedrooms6 Guests
New to Booking
$423
Average price / night
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Charming 2-Bedroom House on Little Torch Key with Pool and Tiki Bar- 28 DAY MIN.
Charming 2-Bedroom House on Little Torch Key with Pool and Tiki Bar- 28 DAY MIN.
House
Little Torch Key, FL, 33042, United States
5.3k from Port Pine Heights center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$260
Average price / night
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FREE KAYAKS & BIKES! Private Pool Home. Little Torch Key. Great Fishing Area.
FREE KAYAKS & BIKES! Private Pool Home. Little Torch Key. Great Fishing Area.
House
little torch key, FL, 33042, United States
5.3k from Port Pine Heights center

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

3 Bedrooms8 Guests
9.8

Exceptional

31 reviews

$416
Average price / night
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Casa de Sueno
Casa de Sueno
House
Little Torch Key, FL, 33042, United States
5.4k from Port Pine Heights center

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

5 Bedrooms10 Guests
8.0

Good

1 reviews

$421
Average price / night
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LiL Piece of Paradise
LiL Piece of Paradise
House
Little Torch Key, FL, 33042, United States
5.5k from Port Pine Heights center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$491
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
5.5k from Port Pine Heights 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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Private Florida Keys Escape w/ Pool, Dock, Tiki Bar – Pet Friendly
Private Florida Keys Escape w/ Pool, Dock, Tiki Bar – Pet Friendly
House
Little Torch Key, FL, 33042, United States
5.6k from Port Pine Heights center

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

4 Bedrooms8 Guests
New to Booking
$434
Average price / night
Check Availability
Starfish - Ocean front with dock and pool
Starfish - Ocean front with dock and pool
House
Little Torch Key, FL, 33042, United States
5.6k from Port Pine Heights center

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

3 Bedrooms6 Guests
10.0

Exceptional

52 reviews

$639
Average price / night
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Conch House - Ocean front with dock and pool
Conch House - Ocean front with dock and pool
House
Little Torch Key, FL, 33042, United States
5.6k from Port Pine Heights center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Grill, Pool

4 Bedrooms8 Guests
10.0

Exceptional

40 reviews

$804
Average price / night
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Tranquility Bayview House-Ocean Front with pool, boat basin and boat ramp
Tranquility Bayview House-Ocean Front with pool, boat basin and boat ramp
House
Little Torch Key, FL, 33042, United States
5.7k from Port Pine Heights center

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

3 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$936
Average price / night
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New pool & Huge master suite! Open water views , 2 stories of wrap around decks
New pool & Huge master suite! Open water views , 2 stories of wrap around decks
House
Summerland Key, FL, 33042, United States
5.7k from Port Pine Heights center

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

3 Bedrooms8 Guests
10.0

Exceptional

14 reviews

$341
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 Port Pine Heights.

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Port Pine Heights Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 80 verified vacation rentals with a private pool in Port Pine Heights. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Port Pine Heights vary depending on the property size, location, and travel season. Rates typically start from around $184 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 Port Pine Heights also welcome pets. Currently, 34 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 Port Pine Heights often include additional features such as Laundry, Pool, and Private Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Port Pine Heights 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.