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

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

  4.  Florida
  5.  Big Pine Key

Refine your search

Price per night

Amenity Filter

Rating

93 Best Vacation Rentals with Pool 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
Check Availability
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
Check Availability
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
Check Availability
🐠 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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
3 BR Canal Home in Big Pine Key, FL - Private Pool/Spa - Great Boating Access!!!
3 BR Canal Home in Big Pine Key, FL - Private Pool/Spa - Great Boating Access!!!
House
Big Pine Key, FL, 33043, United States
1.7k from Big Pine Key center

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

3 Bedrooms6 Guests
New to Booking
$259
Average price / night
Check Availability
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
Check Availability
Family friendly canal home,150 ft dock, easy access to Atl & Gulf
Family friendly canal home,150 ft dock, easy access to Atl & Gulf
House
Big Pine Key, FL, 33043, United States
1.7k from Big Pine Key center

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

5 Bedrooms13 Guests
10.0

Exceptional

1 reviews

$538
Average price / night
Check Availability
Salty Air Retreat
Salty Air Retreat
House
Little Torch Key, FL, USA
5.8k from Big Pine Key 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
Florida Keys Water Front Vacation Home with Pool
Florida Keys Water Front Vacation Home with Pool
House
Big Pine Key, FL, 33043, United States
1.9k from Big Pine Key center

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

3 Bedrooms6 Guests
New to Booking
$296
Average price / night
Check Availability
Parmer's Resort
Parmer's Resort
Resort
Little Torch Key, FL, USA
5.8k from Big Pine Key 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
Awesome Open Water View at Blue Heron Estate
Awesome Open Water View at Blue Heron Estate
House
Big Pine Key, FL, 33043, United States
2.0k from Big Pine Key center

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

4 Bedrooms9 Guests
10.0

Exceptional

63 reviews

$851
Average price / night
Check Availability
Sunshine Key King Travel Trailer 4
Sunshine Key King Travel Trailer 4
House
Big Pine Key, Florida, USA
8.6k from Big Pine Key center

View, Internet, Ocean View, Air Conditioner, Pool, Balcony/Terrace, Laundry

1 Bedroom4 Guests
8.9

Fabulous

20 reviews

$238
Average price / night
Check Availability
Mickey and Lynn's House of Windows
Mickey and Lynn's House of Windows
House
Big Pine Key, FL, 33050, United States
2.0k from Big Pine Key center

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

3 Bedrooms7 Guests
10.0

Exceptional

8 reviews

$403
Average price / night
Check Availability
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
House
Big Pine Key, FL, 33043, United States
2.2k from Big Pine Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$451
Average price / night
Check Availability
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
House
Big Pine Key, FL, 33043, United States
2.3k from Big Pine Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$575
Average price / night
Check Availability
Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and Marina
Cottage
1791 Bogie Drive, Big Pine Key, FL, 33043, United States
2.6k from Big Pine Key center

AC, Barbecue, Free Parking, Heater, Internet, Living Area, Microwave, Outdoor Space, Pool

1 Bedroom4 Guests
8.6

Fabulous

316 reviews

$311
Average price / night
Check Availability
Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage!
Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage!
House
Big Pine Key, FL, 33043, United States
2.7k from Big Pine Key center

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

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$612
Average price / night
Check Availability
Private water front property with ocean access
Private water front property with ocean access
House
Big Pine Key, FL, 33043, United States
2.9k from Big Pine Key center

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

3 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$555
Average price / night
Check Availability
Sunrise Oasis in big pine key
Sunrise Oasis in big pine key
House
Big Pine Key, FL, 33043, United States
3.0k from Big Pine Key center

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

3 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$516
Average price / night
Check Availability
A Serene Florida Escape in Big Pine Key 3 bed 2 bath house, pool, dock, sleep 8
A Serene Florida Escape in Big Pine Key 3 bed 2 bath house, pool, dock, sleep 8
House
Big Pine Key, FL, 33043, United States
3.0k from Big Pine Key center

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

3 Bedrooms8 Guests
New to Booking
$410
Average price / night
Check Availability
Beautiful 2 Bedroom Pool Home On Big Pine Key
Beautiful 2 Bedroom Pool Home On Big Pine Key
House
Big Pine Key, FL, 33043, United States
3.0k from Big Pine Key center

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

2 Bedrooms6 Guests
New to Booking
$311
Average price / night
Check Availability
SEA FOREVER! Gorgeous Ocean-Front Paradise!
SEA FOREVER! Gorgeous Ocean-Front Paradise!
House
Big Pine Key, FL, 33043, United States
3.0k from Big Pine Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Internet, Kitchen

5 Bedrooms12 Guests
New to Booking
$574
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 Big Pine Key.

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

Stay Near Big Pine Key's Top Attractions

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

Big Pine Key Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 93 verified vacation rentals with a pool in Big Pine Key. 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 Big Pine Key vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $178 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Big Pine Key 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 Big Pine Key welcome pets. Currently, 36 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 Big Pine Key often include additional outdoor features such as Pool, Laundry, and Internet. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Big Pine Key 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.