Family-Friendly Vacation Rentals in Port Pine Heights, FL: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  USA

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

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70 Best Family Vacation Rentals in Port Pine Heights (Starting from $161)

Tradewinds Treat
Tradewinds Treat
House
Big Pine Key, FL, USA
0.2k from Port Pine Heights center

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

2 Bedrooms6 Guests
New to Booking
$258
Average price / night
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Newly Remodeled Corner House on the Water
Newly Remodeled Corner House on the Water
House
Big Pine Key, FL, 33043, United States
0.2k from Port Pine Heights center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$211
Average price / night
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Magnolia's By The Sea
Magnolia's By The Sea
House
Big Pine Key, FL, USA
3.3k from Port Pine Heights center

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

2 Bedrooms11 Guests
New to Booking
$474
Average price / night
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Amazing Paradise House Canal Front with access to  Atlantic and Gulf.
Amazing Paradise House Canal Front with access to Atlantic and Gulf.
House
Big Pine Key, FL, 33043, United States
0.2k from Port Pine Heights center

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

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$232
Average price / night
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Cedar Cottage
Cedar Cottage
House
Big Pine Key, FL, USA
3.8k from Port Pine Heights center

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

2 Bedrooms4 Guests
New to Booking
$184
Average price / night
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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
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Reel Paradise
Reel Paradise
House
Big Pine Key, FL, USA
3.8k from Port Pine Heights center

Barbecue/Outdoor Cooking, Internet, Security/Safety, Laundry, Child Friendly

2 Bedrooms6 Guests
New to Booking
$164
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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key Deer Retreat/direct gulf access/hot tub
key Deer Retreat/direct gulf access/hot tub
House
Big Pine Key, FL, USA
5.1k from Port Pine Heights center

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

2 Bedrooms7 Guests
10.0

Exceptional

3 reviews

$310
Average price / night
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Bungalow oasis with lots of room
Bungalow oasis with lots of room
House
Big Pine Key, FL, 33043, United States
2.7k from Port Pine Heights center

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

2 Bedrooms6 Guests
9.2

Superb

5 reviews

$161
Average price / night
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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
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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
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Sunset Villa
Sunset Villa
House
Big Pine Key, FL, USA
5.1k from Port Pine Heights center

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

3 Bedrooms6 Guests
New to Booking
$210
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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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
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Beachside @ Torchview Waterfront Retreat
Beachside @ Torchview Waterfront Retreat
House
Summerland Key, FL, 33042, United States
4.8k from Port Pine Heights center

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

2 Bedrooms6 Guests
10.0

Exceptional

51 reviews

$495
Average price / night
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Big Pine Key Dreams
Big Pine Key Dreams
House
Big Pine Key, FL, USA
5.3k from Port Pine Heights center

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

2 Bedrooms6 Guests
New to Booking
$263
Average price / night
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Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
House
Summerland Key, FL, 33042, United States
4.9k from Port Pine Heights center

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

3 Bedrooms6 Guests
9.6

Exceptional

62 reviews

$494
Average price / night
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Cayo Loco
Cayo Loco
House
Little Torch Key, FL, USA
5.4k from Port Pine Heights center

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

3 Bedrooms6 Guests
New to Booking
$188
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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SEA EVERYWHERE!  Open Water & 2 Boat Basins!
SEA EVERYWHERE! Open Water & 2 Boat Basins!
House
Big Pine Key, FL, 33043, United States
5.1k from Port Pine Heights center

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

4 Bedrooms9 Guests
New to Booking
$462
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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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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Private water front property with ocean access
Private water front property with ocean access
House
Big Pine Key, FL, 33043, United States
5.3k from Port Pine Heights center

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

3 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$555
Average price / night
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Oceanfront Paradise w new 365' Dock Huge Tiki and Firepit.  Dogs OK
Oceanfront Paradise w new 365' Dock Huge Tiki and Firepit. Dogs OK
House
Big Pine Key, FL, 33043, United States
5.3k from Port Pine Heights center

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

3 Bedrooms6 Guests
9.4

Superb

20 reviews

$463
Average price / night
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OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
House
Little Torch Key, FL, 33042, United States
5.4k from Port Pine Heights center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
9.2

Superb

108 reviews

$801
Average price / night
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Incredible~Ocean Views~ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
Incredible~Ocean Views~ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
House
Big Pine Key, FL, 33043, United States
5.5k from Port Pine Heights center

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

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$513
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 Family Vacation Rentals in Port Pine Heights.

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Port Pine Heights Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 70 verified family-friendly vacation rentals in Port Pine Heights. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Port Pine Heights vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $161 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Port Pine Heights offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Port Pine Heights are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Port Pine Heights often include amenities such as Child Friendly, Laundry, and Balcony/Terrace. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.