Cruise And Resorts - Vacation Rentals in Whispering Pines

Frigate's Nest in Little Torch From US $2,126
         

8.0 (4 Reviews)
House
  • Air Conditioner
  • Pool
  • TV
Waterfront Cozy Cottage with Boat Ramp & Dock! From US $536
         

10.0 (66 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Conch House on a Quiet Canal : Monthly Only From US $215
         

9.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Starfish - Ocean front with dock and pool From US $756
         

10.0 (53 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Whispering Pines

Over 387+ Luxury Places to Stay in or Near Whispering Pines
Fishermen`s Paradise From US $1,127
         

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9.0 (1 Review)
House
  • Pool
  • Security/Safety
  • Barbecue/Outdoor Cooking
Stunning 5 Bedroom Open Water Pool Home With Great Boating From US $1,022
         

Waterfront Beach House with Dock & Heated Pool! From US $927
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Conch House - Ocean front with dock and pool From US $865
         

10.0 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Whispering Pines

Over 158+ Top-Rated Vacation Rentals with a Pool in or Near Whispering Pines
Beautiful Open-Water Property From US $576
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
Mickey and Lynn's House of Windows From US $403
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut From US $420
         

10.0 (7 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 Whispering Pines

Over 173+ Pet-Friendly Vacation Rentals in or Near Whispering Pines
key Deer Retreat/direct gulf access/hot tub From US $310
         

9.4 (6 Reviews)
House
  • Parking
  • Pet Friendly
  • Security/Safety
Old Wooden Bridge Resort and Marina From US $275
         

8.6 (344 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautiful House on Canal - minutes to the Atlantic, no bridges From US $304
         

Manatee Watch | 5 bedrooms, pool, ocean access From US $639
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
Canal Front Home With Pool And Hot Tub From US $263
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Whispering Pines

Over 40+ Large Vacation Homes & Villas in or Near Whispering Pines
Sunrise Oasis in big pine key From US $517
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Old Wooden Bridge Resort & Marina From US $257
         

8.0 (315 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Little Torch Key Nest - Ocean view with pool From US $846
         

5-4 house with canal and pool From US $379
         

Hibiscus House - Heated Pool From US $158
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Whispering Pines

Over 4+ Wheelchair Accessible Vacation Homes in or Near Whispering Pines
Beautiful Keys Home w/Open Water Views & 90' Dock From US $421
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Parmer's Resort From US $304
         

8.6 (412 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Florida Keys Pine Canal Water Front - Deep Canal From US $216
         

Whispering Pines Vacation Rentals and Airbnb Places to Stay Under $200

Over 65+ Whispering Pines Vacation Rentals and Airbnb Places to Stay Under $200
Reel Paradise From US $164
         

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New
House
  • Security/Safety
  • Barbecue/Outdoor Cooking
  • Child Friendly
Bungalow oasis with lots of room From US $163
         

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

Instantly Bookable Vacation Homes in Whispering Pines

Over 186+ Instantly Bookable Vacation Homes in or Near Whispering Pines
Luxury and Lovely Water Front House From US $590
         

10.0 (6 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
LiL Piece of Paradise From US $366
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Unwind in the Keys! Extended-Stay Big Pine Home From US $252
         

About Whispering Pines Vacation Rentals

With more than 396 Whispering Pines vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cruiseandresorts 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 Whispering Pines.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruiseandresorts Whispering Pines, 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 Whispering Pines. Places to stay near Whispering Pines are 764.9 ft² on average, with prices averaging US $415 a night.

Cruiseandresorts makes it easy and safe to find and compare vacation rentals in Whispering Pines 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 Whispering Pines

Type Count
Vacation Homes 334
Hotels 27
Holiday Apartments 11
B&B 7
Cottages 7
Cabin Rentals 3
Others 2
Resorts 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Whispering Pines

Pro Tip: Cruiseandresorts makes it easy to compare the best listings on Cruiseandresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruiseandresorts 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 Whispering Pines.

Weather in Whispering Pines

View the weather forecast for Whispering Pines before booking your Whispering Pines Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Whispering Pines Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Whispering Pines?

Currently, the total number of properties listed in 2026 is over 396 in the Whispering Pines area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Whispering Pines.