Short-Term Rentals in Port Pine Heights, FL: Compare 10+ Sites & Save

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  3.  USA

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

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303 Best Short-Term Rentals in Port Pine Heights (Starting from $148)

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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House 2 bedroom  2 bath Large enclosed porch overlooking canal with boat dock
House 2 bedroom 2 bath Large enclosed porch overlooking canal with boat dock
House
Big Pine Key, FL, 33043, United States
0.1k from Port Pine Heights center

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

2 Bedrooms6 Guests
New to Booking
$178
Average price / night
Check Availability
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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Newly Renovated Boater’s Paradise -35' Dock + Ice • No Low Bridges
Newly Renovated Boater’s Paradise -35' Dock + Ice • No Low Bridges
House
Big Pine Key, FL, 33043, United States
0.2k from Port Pine Heights center

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

2 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$262
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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Pristine Waterfront Charmer - Outdoor Living & Dining, Dock, AC - Snowbirds OK
Pristine Waterfront Charmer - Outdoor Living & Dining, Dock, AC - Snowbirds OK
House
Big Pine Key, FL, 33043, United States
0.2k from Port Pine Heights center

2 Bedrooms6 Guests
New to Booking
$332
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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Fisherman’s Paradise - Ocean & Gulf Access!  Key Deer Preserve.  TIME TO FISH!
Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
House
Big Pine Key, FL, 33043, United States
0.2k from Port Pine Heights center

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

3 Bedrooms6 Guests
10.0

Exceptional

17 reviews

$159
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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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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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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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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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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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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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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1 story  3-bedroom house in tranquil Big Pine Key 100 ft dock
1 story 3-bedroom house in tranquil Big Pine Key 100 ft dock
House
Big Pine Key, FL, 33043, United States
0.3k from Port Pine Heights center

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

3 Bedrooms12 Guests
New to Booking
$267
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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Updated Canal Home with Dock for 25' Boat, Sandbar Access & Backcountry Fishing
Updated Canal Home with Dock for 25' Boat, Sandbar Access & Backcountry Fishing
House
Big Pine Key, FL, 33043, United States
0.3k from Port Pine Heights center

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

2 Bedrooms4 Guests
New to Booking
$204
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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\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"
\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"
House
Big Pine Key, FL, 33043, United States
0.3k from Port Pine Heights center

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

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$293
Average price / night
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Relaxing Florida Keys canal front home in nature preserve
Relaxing Florida Keys canal front home in nature preserve
House
Big Pine Key, FL, 33043, United States
0.3k from Port Pine Heights center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$148
Average price / night
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Boater’s Paradise: 3BR Canal Front Home + Fish Cleaning Station
Boater’s Paradise: 3BR Canal Front Home + Fish Cleaning Station
House
Big Pine Key, FL, 33043, United States
0.3k from Port Pine Heights center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$225
Average price / night
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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
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
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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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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Monthly rental  lap pool 40 ft dock wDavitz
Monthly rental lap pool 40 ft dock wDavitz
House
Big Pine Key, FL, 33043, United States
0.7k from Port Pine Heights center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms6 Guests
New to Booking
$387
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 Short-Term Rentals in Port Pine Heights.

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Port Pine Heights Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 303 verified short-term rentals in Port Pine Heights, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Port Pine Heights vary depending on location, property size, and travel dates. Rates typically start from around $148 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Port Pine Heights include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Port Pine Heights, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Port Pine Heights often include amenities such as Laundry, Fireplace/Heating, and Balcony/Terrace, providing a comfortable and convenient stay.

Short-term rentals in Port Pine Heights are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.