Surfside Vacation Rental - Vacation Rentals in Big Pine Key

Sunshine Key King Travel Trailer 4 From US $238
         

|
8.9 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunshine Key RV Resort & Marina From US $343
         

8.8 (163 Reviews)
House
  • Air Conditioner
  • Pool
  • TV
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut From US $580
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Big Pine Key

Over 297+ Luxury Places to Stay in or Near Big Pine Key
Fishermen`s Paradise From US $1,127
         

New
House
  • Pool
  • Security/Safety
  • Barbecue/Outdoor Cooking
Stunning 5 Bedroom Open Water Pool Home With Great Boating From US $1,017
         

Tiki Beach - Big Pine Key From US $831
         

6.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Big Pine Key

Over 99+ Top-Rated Vacation Rentals with a Pool in or Near Big Pine Key
Mickey and Lynn's House of Windows From US $403
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Canal Front Home in Big Pine Key with Pool From US $283
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Big Pine Key

Over 140+ Pet-Friendly Vacation Rentals in or Near Big Pine Key
Deer Run on the Atlantic From US $500
         

|
10.0 (3 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Old Wooden Bridge Resort and Marina From US $423
         

8.6 (309 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Manatee Watch | 5 bedrooms, pool, ocean access From US $575
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
Canal Front Home With Pool And Hot Tub From US $224
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Escape the Ordinary and Experience Island Paradise From US $242
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Tarpon Tales | Fantastic boating, pet-friendly From US $241
         

Large Vacation Homes & Villas in Big Pine Key

Over 33+ Large Vacation Homes & Villas in or Near Big Pine Key
Big Pine Key House 4/2 with 75’ dock and a stunning bay view. From US $255
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Old Wooden Bridge Resort & Marina From US $257
         

8.2 (287 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunrise Oasis in big pine key From US $517
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hibiscus House - Heated Pool From US $400
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private water front property with ocean access From US $555
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Big Pine Key

Over 3+ Wheelchair Accessible Vacation Homes in or Near Big Pine Key
Big Pine Key Dreams From US $263
         

|
New
House
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace
Florida Keys Pine Canal Water Front - Deep Canal From US $216
         

Big Pine Key Vacation Rentals and Airbnb Places to Stay Under $200

Over 47+ Big Pine Key Vacation Rentals and Airbnb Places to Stay Under $200
RV In The Keys a Tropical Retreat From US $179
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bungalow oasis with lots of room From US $161
         

9.2 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Captain & Mermaid's Diamond #BP25 From US $197
         

Instantly Bookable Vacation Homes in Big Pine Key

Over 125+ Instantly Bookable Vacation Homes in or Near Big Pine Key
Luxury and Lovely Water Front House From US $626
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Dates available Oct, Nov, Dec 2023 From US $236
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Big Pine Key Vacation Rentals

With more than 306 Big Pine Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Surfsidevacationrental and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Big Pine Key.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Surfsidevacationrental Big Pine Key, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Big Pine Key. Places to stay near Big Pine Key are 779.87 ft² on average, with prices averaging $387 a night.

Surfsidevacationrental makes it easy and safe to find and compare vacation rentals in Big Pine Key with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Big Pine Key

Type Count
Vacation Homes 273
Holiday Apartments 11
B&B 9
Cabin Rentals 3
Cottages 3
Hotels with Suites 2
Others 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Big Pine Key

Pro Tip: Surfsidevacationrental makes it easy to compare the best listings on Surfsidevacationrental homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Surfsidevacationrental homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Big Pine Key.

Weather in Big Pine Key

View the weather forecast for Big Pine Key before booking your Big Pine Key Vacation Rentals to confirm your best time to go.

December - February
High 81°F       Low 67°F
March - May
High 87°F       Low 70°F
June - August
High 91°F       Low 80°F
September - November
High 90°F       Low 73°F

Big Pine Key Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Big Pine Key?
How many vacation rentals have private pools in Big Pine Key?
How many vacation rentals are available in Big Pine Key?

Currently, the total number of properties listed in 2026 is over 306 in the Big Pine Key area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Big Pine Key.