Vacation Rentals in Big Pine Key, FL: Compare 10+ Sites & Save

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264 Best Vacation Rentals in Big Pine Key (Starting from $178)

Fishermen`s Paradise
Fishermen`s Paradise
House
Big Pine Key, FL, USA
1.6k from Big Pine Key center

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

3 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$1127
Average price / night
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Stunning 5 Bedroom Open Water Pool Home With Great Boating
Stunning 5 Bedroom Open Water Pool Home With Great Boating
House
Big Pine Key, FL, 33043, United States
0.8k from Big Pine Key center

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

5 Bedrooms10 Guests
New to Booking
$1021
Average price / night
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Tiki Beach - Big Pine Key
Tiki Beach - Big Pine Key
House
Big Pine Key, FL, USA
1.6k from Big Pine Key center

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

4 Bedrooms10 Guests
New to Booking
$831
Average price / night
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Charming 3-bedroom house in \nBig Pine Key near Beach and Key West
Charming 3-bedroom house in \nBig Pine Key near Beach and Key West
House
Big Pine Key, FL, 33043, United States
1.1k from Big Pine Key center

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

3 Bedrooms11 Guests
8.0

Good

9 reviews

$738
Average price / night
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Old Wooden Bridge Resort & Marina
Old Wooden Bridge Resort & Marina
Cabin
Big Pine Key, FL, USA
2.6k from Big Pine Key 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
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3bd/2.5 bath comfortable home with large dock located on a direct access canal!
3bd/2.5 bath comfortable home with large dock located on a direct access canal!
House
Big Pine Key, FL, 33043, United States
1.1k from Big Pine Key center

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

3 Bedrooms9 Guests
2.0

Review score

1 reviews

$359
Average price / night
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Hellenga Haven
Hellenga Haven
House
Big Pine Key, FL, USA
2.9k from Big Pine Key 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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Boater's Paradise with Boat Dock / Quick Open Water Access
Boater's Paradise with Boat Dock / Quick Open Water Access
House
Big Pine Key, FL, 33043, United States
1.2k from Big Pine Key center

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

2 Bedrooms4 Guests
8.0

Good

3 reviews

$227
Average price / night
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Big Pine Key Dreams
Big Pine Key Dreams
House
Big Pine Key, FL, USA
2.9k from Big Pine Key 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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The Friendly Pelican\n2-BDR 2-BATH on a canal w/AC in Big Pine Key
The Friendly Pelican\n2-BDR 2-BATH on a canal w/AC in Big Pine Key
House
Big Pine Key, FL, 33043, United States
1.2k from Big Pine Key center

AC, Barbecue, Dryer, Free Parking, Laundry, Living Area, Microwave, No Smoking, TV

2 Bedrooms6 Guests
New to Booking
$196
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
3.1k from Big Pine Key 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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Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
House
Big Pine Key, FL, 33043, United States
1.2k from Big Pine Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

34 reviews

$330
Average price / night
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Sunset Villa
Sunset Villa
House
Big Pine Key, FL, USA
3.1k from Big Pine Key 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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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
1.2k from Big Pine Key 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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RV In The Keys a Tropical Retreat
RV In The Keys a Tropical Retreat
House
Big Pine Key, FL, USA
3.6k from Big Pine Key center

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

1 Bedroom4 Guests
New to Booking
$178
Average price / night
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Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home
Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home
House
Big Pine Key, FL, 33043, United States
1.2k from Big Pine Key center

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

3 Bedrooms6 Guests
New to Booking
$423
Average price / night
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Florida Keys /Big Pine Key/ Dear Haven
Florida Keys /Big Pine Key/ Dear Haven
Apartment
Big Pine Key, Florida, USA
3.7k from Big Pine Key center

Air Conditioner, Parking

2 Bedrooms4 Guests
New to Booking
$7000
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
1.2k from Big Pine Key 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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Sunset Retreat
Sunset Retreat
House
Big Pine Key, FL, USA
4.4k from Big Pine Key center

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

3 Bedrooms6 Guests
New to Booking
$742
Average price / night
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Peaceful Big Pine Tropical Seaside-BP#22
Peaceful Big Pine Tropical Seaside-BP#22
House
Big Pine Key, FL, 33043, United States
1.3k from Big Pine Key center

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

3 Bedrooms8 Guests
New to Booking
$274
Average price / night
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Open 360 water view,  boat dockage, 4 bedroom Home in Big Pine Key
Open 360 water view, boat dockage, 4 bedroom Home in Big Pine Key
House
Big Pine Key, FL, 33043, United States
1.3k from Big Pine Key center

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

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$623
Average price / night
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Captain & Mermaid's Diamond #BP25
Captain & Mermaid's Diamond #BP25
House
Big Pine Key, FL, 33043, United States
1.3k from Big Pine Key center

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

1 Bedroom4 Guests
New to Booking
$196
Average price / night
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Keys Breeze | 2 bedroom, 2 bath canalfront home
Keys Breeze | 2 bedroom, 2 bath canalfront home
House
Big Pine Key, FL, 33043, United States
1.3k from Big Pine Key center

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

2 Bedrooms4 Guests
New to Booking
$264
Average price / night
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Yeya's Hideaway | 4 bedrooms, POOL on the way by 2027!
Yeya's Hideaway | 4 bedrooms, POOL on the way by 2027!
House
Big Pine Key, FL, 33043, United States
1.3k from Big Pine Key center

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

4 Bedrooms12 Guests
New to Booking
$490
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
1.5k from Big Pine Key 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
1.5k from Big Pine Key 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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Boat dockage & a great Gulf-front Big Pine retreat
Boat dockage & a great Gulf-front Big Pine retreat
House
Big Pine Key, FL, 33043, United States
1.6k from Big Pine Key center

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

4 Bedrooms10 Guests
9.0

Fabulous

4 reviews

$1149
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 in Big Pine Key.

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Frequently Asked Questions

You can explore 264 verified vacation rentals in Big Pine Key. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Big Pine Key vary depending on the season, property size, and location. Rates typically start from around $178 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Big Pine Key include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Big Pine Key welcome pets. Currently, 39 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Big Pine Key often include amenities such as Laundry, Internet, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.