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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

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

Refine your search

Price per night

Amenity Filter

Rating

128 Best Vacation Rentals with Pool in Port Pine Heights (Starting from $160)

Salty Air Retreat
Salty Air Retreat
House
Little Torch Key, FL, USA
5.1k from Port Pine Heights center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$656
Average price / night
Check Availability
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
Check Availability
Hellenga Haven
Hellenga Haven
House
Big Pine Key, FL, USA
5.2k from Port Pine Heights center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$411
Average price / night
Check Availability
Sunset Hideaway, Pool home on canal
Sunset Hideaway, Pool home on canal
House
Big Pine Key, FL, 33043, United States
0.3k from Port Pine Heights center

AC, Dryer, Internet, Laundry, No Smoking, Outdoor Grill, Pool, TV, Washer

3 Bedrooms6 Guests
New to Booking
$361
Average price / night
Check Availability
Parmer's Resort
Parmer's Resort
Resort
Little Torch Key, FL, USA
5.5k from Port Pine Heights center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, Lodgings, Beach, Places to stay

29 Bedrooms37 Guests
8.6

Fabulous

440 reviews

$215
Average price / night
Check Availability
NEWLY RENOVATED 3/2 WITH POOL AND CANAL ACCESS!!!
NEWLY RENOVATED 3/2 WITH POOL AND CANAL ACCESS!!!
House
Big Pine Key, FL, 33043, United States
0.5k from Port Pine Heights center

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

3 Bedrooms8 Guests
New to Booking
$318
Average price / night
Check Availability
Old Wooden Bridge Resort & Marina
Old Wooden Bridge Resort & Marina
Cabin
Big Pine Key, FL, USA
5.6k from Port Pine Heights center

Accommodations, Pools, Parking, Lodges, Cabins, Pet-friendly, Lodgings, Places to stay

43 Bedrooms138 Guests
8.4

Very Good

241 reviews

$257
Average price / night
Check Availability
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW
House
Big Pine Key, FL, 33043, United States
0.5k from Port Pine Heights center

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

3 Bedrooms6 Guests
8.8

Fabulous

16 reviews

$327
Average price / night
Check Availability
RV In The Keys a Tropical Retreat
RV In The Keys a Tropical Retreat
House
Big Pine Key, FL, USA
6.6k from Port Pine Heights center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$178
Average price / night
Check Availability
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
Check Availability
Sunset Retreat
Sunset Retreat
House
Big Pine Key, FL, USA
7.6k from Port Pine Heights center

Barbecue/Outdoor Cooking, Pool, Internet, Laundry, Child Friendly

3 Bedrooms6 Guests
New to Booking
$742
Average price / night
Check Availability
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
Check Availability
Fishermen`s Paradise
Fishermen`s Paradise
House
Big Pine Key, FL, USA
8.4k from Port Pine Heights center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$1127
Average price / night
Check Availability
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
Check Availability
Tiki Beach - Big Pine Key
Tiki Beach - Big Pine Key
House
Big Pine Key, FL, USA
8.5k from Port Pine Heights center

Pool, Parking, Security/Safety, View, Sports/Activities, Spa, Barbecue/Outdoor Cooking

4 Bedrooms10 Guests
New to Booking
$831
Average price / night
Check Availability
FISHERMANS DREAM HOUSE
FISHERMANS DREAM HOUSE
House
Big Pine Key, FL, 33043, United States
3.9k from Port Pine Heights center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Patio, Pool, Washer

3 Bedrooms8 Guests
New to Booking
$341
Average price / night
Check Availability
Summerland Canal
Summerland Canal
House
Summerland Key, FL, USA
8.8k from Port Pine Heights center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms5 Guests
New to Booking
$160
Average price / night
Check Availability
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
Check Availability
Skyway Living
Skyway Living
House
Summerland Key, FL, USA
8.8k from Port Pine Heights center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

2 Bedrooms6 Guests
New to Booking
$237
Average price / night
Check Availability
Tropical 5BR Paradise,  Private Pool, Hot Tub, Canal Access – Sleeps 12
Tropical 5BR Paradise, Private Pool, Hot Tub, Canal Access – Sleeps 12
House
Big Pine Key, FL, 33043, United States
4.1k from Port Pine Heights center

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

5 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$468
Average price / night
Check Availability
Canal Front Home in Big Pine Key with Pool
Canal Front Home in Big Pine Key with Pool
House
BIG PINE KEY, FL, 33043, United States
4.1k from Port Pine Heights center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$283
Average price / night
Check Availability
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
Check Availability
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
Check Availability
Private 1 Acre property outdoor retreat on boatable canal- Monthly Rental!
Private 1 Acre property outdoor retreat on boatable canal- Monthly Rental!
House
Summerland Key, FL, 33042, United States
4.5k from Port Pine Heights center

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

3 Bedrooms8 Guests
New to Booking
$264
Average price / night
Check Availability
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
Check Availability
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
Check Availability
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
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 Pool in Port Pine Heights.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Stay Near Port Pine Heights's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Port Pine Heights Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 128 verified vacation rentals with a pool in Port Pine Heights. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Port Pine Heights vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $160 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Port Pine Heights offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Port Pine Heights welcome pets. Currently, 37 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Port Pine Heights often include additional outdoor features such as Pool, Laundry, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Port Pine Heights offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.