Surfside Vacation Rental - Vacation Rentals in Long Pine Key

Beautiful and Cozy 3- bedroom townhouse From US $243
         

10.0 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Damari Soto From US $342
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Hoosville Hostel From US $78
         

8.0 (152 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
CozyHouse: Near National Parks Between Miami & The Keys From US $183
         

Cozy Studio Close to the Keys From US $97
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Travelodge by Wyndham Florida City/Homestead/Everglades From US $102
         

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9.2 (1885 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Cozy Green Apartment From US $125
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Tru by Hilton Florida City From US $107
         

9.0 (192 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Homestead Green retreat From US $272
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Perfect 5-bedroom house with AC in cool Florida City From US $637
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunny Oasis with Private Pool, Sunny Oasis with Private Pool From US $502
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Green Keys Ranch From US $268
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Green Apartment From US $193
         

10.0 (1 Review)
Apartment
  • Balcony/Terrace
  • Security/Safety
  • Child Friendly
Cozy, Historic Family Home From US $435
         

9.8 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Garden House, Pool in Lush Peaceful Homestead From US $492
         

9.8 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Cozy bedroom near Florida Keys From US $115
         

9.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Heated Pool Family Retreat- Games/Everglades/Keys From US $590
         

9.2 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Family Home near Everglades, FL Keys, Miami From US $236
         

9.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 1-bedroom studio in marvelous Florida City From US $97
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Casa Serenity - 4BR Homes for big families - Near Florida Keys! From US $321
         

7.6 (4 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
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 Long Pine Key.

Weather in Long Pine Key

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

December - February
High 79°F       Low 52°F
March - May
High 91°F       Low 55°F
June - August
High 92°F       Low 73°F
September - November
High 90°F       Low 58°F

Long Pine Key Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Long Pine Key?
How many vacation rentals are available in Long Pine Key?

Currently, the total number of properties listed in 2026 is over 175 in the Long Pine Key area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Long Pine Key.