Short-Term Rentals in Big Pine Key, FL: Compare 10+ Sites & Save

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263 Best Short-Term 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 Short-Term Rentals in Big Pine Key.

Where to stay in Big Pine Key? Best neighborhoods & areas

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

Big Pine Key Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 263 verified short-term rentals in Big Pine Key, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Big Pine Key vary depending on location, property size, and travel dates. Rates typically start from around $178 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Big Pine Key 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 Big Pine Key, 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 Big Pine Key often include amenities such as Laundry, Internet, and Balcony/Terrace, providing a comfortable and convenient stay.

Short-term rentals in Big Pine Key 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.