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Big Pine Key, FL accommodations
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410 Lodgings in Big Pine Key, FL

Top Lodgings with a Pool in Big Pine Key, FL

These lodgings in Big Pine Key, FL include a swimming pool, the perfect way to complement a day by the water.

New Deluxe Duplex Unit, 2 Queen Beds, Unit H-5 - Big Pine Key, FL
9.9 61 reviews
Big Pine Key, FL
10/13 – 10/15
$476/nighttotal: $952 (2 )

New Deluxe Duplex Unit, 2 Queen Beds, Unit H-5

1 3
apartment , Big Pine Key
This two-bedroom apartment is peacefully situated in Big Pine Key, just a short distance from the beach and close to local shops and restaurants. The tranquil atmosphere makes it ideal for families seeking a relaxing getaway.
The rental sleeps up to six guests and offers a well-equipped kitchen with a refrigerator, microwave, and dishwasher. Enjoy the tropical climate in the garden, take a dip in the swimming pool, or simply relax in the air-conditioned apartment.
Rv In The Keys | Tropical Retreat - Big Pine Key, FL
9.3 26 reviews
Big Pine Key, FL
12/01 – 12/04
$291/nighttotal: $873 (3 )

Rv In The Keys | Tropical Retreat

1 1
cabin , Big Pine Key
"Rv In The Keys" offers a Big Pine Key campervan rental conveniently located in an RV park, 30 miles from Key West and 20 miles from Marathon, providing easy access to both destinations.
This one-bedroom, one-bathroom toy hauler sleeps four, features a full kitchen with fridge, freezer, and microwave, and boasts on-site amenities including a swimming pool, laundry facilities, and BBQ grills, plus a unique convertible patio for indoor/outdoor living.
2 Bedroom Turquoise Cabin - Big Pine Key, FL
9.1 33 reviews
Big Pine Key, FL
10/13 – 10/15
$330/nighttotal: $660 (2 )

2 Bedroom Turquoise Cabin

1 3
cabin , Big Pine Key
This cozy cabin is located in Big Pine Key, just a short drive from the beautiful Bahia Honda State Park and the charming downtown area. The cabin has consistently received excellent ratings for its location, cleanliness, and overall experience.
This comfortable cottage offers two bedrooms and one bathroom, comfortably accommodating up to seven guests. Amenities include a fully equipped kitchen, air conditioning, a private swimming pool, a lush garden, and free parking.
300 Private Beach, Pool & Rooftop W Panoramic Ocean Views - Big Pine Key, FL
10 2 reviews
Big Pine Key, FL
07/25 – 08/22
$1210/nighttotal: $33880 (28 )

300 Private Beach, Pool & Rooftop W Panoramic Ocean Views

4 6
apartment , Big Pine Key
This beachfront Long Beach Estates home offers direct access to Coupon Bight Aquatic Preserve and is within five minutes of Cook Island and Newfound Harbor Keys.
This 2,590-square-foot vacation rental boasts four bedrooms, four bathrooms, a private pool, and can comfortably accommodate up to ten guests, featuring a fully equipped kitchen, laundry facilities, and outdoor barbecue grills.

Best family friendly Big Pine Key, FL lodging

Among the 410 accommodations in Big Pine Key, FL, here are the 4 best for families

Waterfront Captain House With Boat Basin & Ramp! - Big Pine Key, FL
9.8 8 reviews
Big Pine Key, FL
10/13 – 10/15
$975/nighttotal: $1950 (2 )

Waterfront Captain House With Boat Basin & Ramp!

3 3
apartment , Big Pine Key
This Summerland Key vacation home is located three miles from Florida Keys Beaches and the Big Pine Key Flea Market, and six miles from the Key West Visitor Center.
This three-bedroom, two-bathroom house offers 1,530 square feet of space, accommodating up to eight guests and boasting a private patio, Jacuzzi, and fully equipped kitchen including a dishwasher.
Luxury And Lovely Water Front House - Big Pine Key, FL
9.8 54 reviews
Big Pine Key, FL
10/01 – 10/09
$567/nighttotal: $4536 (8 )

Luxury And Lovely Water Front House

3 2
apartment , Big Pine Key
This waterfront vacation home is located in Big Pine Key, just a short distance from Coupon Bight Aquatic Preserve, the National Key Deer Refuge Visitor Center, and the Big Pine Key Flea Market. It has excellent user, location, and cleanliness ratings.
This two-bedroom house has a sofa bed and free Wi-Fi. It features a fully equipped kitchen, a private garden, a terrace, and parking.
135 M² House ∙ 3 Bedrooms ∙ 6 Guests - Big Pine Key, FL
Big Pine Key, FL
07/25 – 08/22
$233/nighttotal: $6524 (28 )

135 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 6
house , Big Pine Key
This canal-front home in a serene waterfront district of Big Pine Key offers direct access with dockage for boats up to 35 feet.
This 1440 square foot residence accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring a gourmet kitchen, air conditioning, internet, parking, and included kayaks and bicycles for exploring the waterways.
Sterling Bay House - Big Pine Key, FL
10 5 reviews
Big Pine Key, FL
10/01 – 10/09
$2883/nighttotal: $23064 (8 )

Sterling Bay House

1 2
apartment , Big Pine Key
This Big Pine Key apartment is directly on the water with plenty of dock space and is a short boat ride to Picnic Island and Content Key. It has been rated excellent for location, cleanliness, and user experience.
This 6-bedroom, 6-bathroom home comfortably accommodates 16 guests. It includes a private pool, a game room, a fully-equipped bar area, and various outdoor lounging and dining spaces.

Frequently Asked Questions about accommodations in Big Pine Key, FL

  • What outdoor activities can visitors enjoy in and around Big Pine Key, FL?

    Big Pine Key is a paradise for outdoor enthusiasts. You can go fishing, kayaking, diving, snorkeling, or just relax on the beach. There are also plenty of hiking and biking trails in the area, like the one along the Overseas Highway. If you're feeling adventurous, you can even rent a boat and explore the backcountry.
  • What are the best accommodations in Big Pine Key, FL?

    Among the accommodations in Big Pine Key, FL, Little Torch Cottages, Old Island Life and Old Wooden Bridge Resort & Marina are the most popular ones.

  • When is the ideal time to plan a trip to Big Pine Key, FL?

    The best time to visit Big Pine Key is during the winter months, from November to April, when the weather is warm and sunny. You'll avoid the summer humidity and the hurricane season, which runs from June to November. But even during the summer, you can find some great deals and enjoy the less crowded beaches.
  • What are the best accommodations with a pool in Big Pine Key, FL?

    Little Torch Cottages, Old Wooden Bridge Resort & Marina and Looe Key Reef Resort And Dive Center are the best accommodations with a pool in Big Pine Key, FL.

  • What are the best walking or cycling routes in Big Pine Key, FL?

    The Overseas Highway is a great place to walk or bike, especially on the weekends when traffic is lighter. You can also explore the Big Pine Key National Wildlife Refuge on foot or by bike. There's a nice paved trail that goes through the refuge, offering beautiful views of the mangrove forests and the ocean.
  • What are the best accommodations with a jacuzzi in Big Pine Key, FL?

  • What nearby towns or cities can be explored from Big Pine Key, FL?

    Big Pine Key is a great base for exploring the rest of the Florida Keys. You can easily drive to Key West, Marathon, and Islamorada, all of which have their own unique charm and attractions. If you're looking for a more laid-back experience, you can also check out the smaller towns of Cudjoe Key and Summerland Key.
  • What are the best accommodations for families and kids in Big Pine Key, FL?

  • What amenities can travelers expect from accommodations in Big Pine Key, FL?

    You'll find a variety of accommodations in Big Pine Key, from cozy guesthouses to luxurious resorts. Many places offer swimming pools, restaurants, and bars, as well as amenities like boat docks and fishing charters. You can also find places with direct access to the beach.
  • What are the best pet friendly accommodations in Big Pine Key, FL?

    The best pet friendly accommodations in Big Pine Key, FL are Little Torch Cottages, Old Wooden Bridge Resort & Marina and Looe Key Reef Resort And Dive Center.

  • What are the best accommodations with parking in Big Pine Key, FL?

    Little Torch Cottages, Old Island Life and Old Wooden Bridge Resort & Marina are the best accommodations with parking in Big Pine Key, FL.

Destinations nearby

Best Big Pine Key, FL accommodation with a balcony

Frigate's Nest Extraordinary 8bed/8bath Nightly Rental With Dockage & Private Pool - Big Pine Key, FL
8.0 4 reviews
Big Pine Key, FL
10/01 – 10/09
$2205/nighttotal: $17640 (8 )

Frigate's Nest Extraordinary 8bed/8bath Nightly Rental With Dockage & Private Pool

8 2
apartment , Big Pine Key
This waterfront estate in Little Torch Key offers an exclusive retreat with open water views, located a short drive from Looe Key Reef and Summerland Key attractions.
This expansive 8-bedroom, 8-bathroom residence accommodates up to 16 guests and features a private pool, dockage, two living areas, two propane grills, and kayaks, with central air conditioning and WiFi provided.
Free Kayaks & Bikes! Private Pool Home. Little Torch Key. Great Fishing Area. - Big Pine Key, FL
9.8 32 reviews
Big Pine Key, FL
07/25 – 08/22
$280/nighttotal: $7840 (28 )

Free Kayaks & Bikes! Private Pool Home. Little Torch Key. Great Fishing Area.

3 6
apartment , Big Pine Key
This apartment is located on Little Torch Key, a small island just off the Overseas Highway (US Route 1) at mile marker 28, offering a peaceful and secluded getaway. The property is approximately 30 minutes from Key West and 20 minutes from Marathon. Guests have consistently rated this rental as excellent.
This 3-bedroom, 3-bathroom apartment is perfect for families or groups of up to 8 people. The apartment has a private pool, a hot tub, a wet bar, a barbecue area, and a large dock for fishing and boating.
Beach View Room Dormitory Room Barnacle Resort - Big Pine Key, FL
Big Pine Key, FL
12/01 – 12/04
$441/nighttotal: $1323 (3 )

Beach View Room Dormitory Room Barnacle Resort

1 1
apartment , Big Pine Key
This oceanfront apartment rental in Long Beach Estates, Big Pine Key, is 6.8 miles from Bahia Honda State Park and 34 miles from Key West.
The 500-square-foot unit features one bedroom, one bathroom, accommodates two guests, and includes a kitchen, air conditioning, a terrace, private beach access, complimentary kayaks and bicycles, and proximity to local restaurants and supermarkets.
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax In Paradise! - Big Pine Key, FL
10 34 reviews
Big Pine Key, FL
07/25 – 08/22
$337/nighttotal: $9436 (28 )

Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax In Paradise!

3 6
apartment , Big Pine Key
This waterfront apartment is located in Sands, a neighborhood in Big Pine Key, just minutes from the beach and National Seashore park. It has consistently received excellent user ratings, making it a popular choice for travelers. The apartment features three bedrooms and two bathrooms, offering ample space for up to six guests. You'll enjoy access to a range of amenities, including a private porch deck, kayaks, bikes, and stand-up paddleboards, as well as a garden, a spa, and parking.

Neighborhoods and points of interest in Big Pine Key, FL

Best Big Pine Key, FL accommodation with a kitchen

Dates Available Oct, Nov, Dec 2023 - Big Pine Key, FL
9.9 19 reviews
Big Pine Key, FL
07/25 – 08/22
$197/nighttotal: $5516 (28 )

Dates Available Oct, Nov, Dec 2023

1 6
apartment , Big Pine Key
This Big Pine Key vacation home in Doctor's Arm offers convenient access to Blue Hole (within 3 miles), the National Key Deer Refuge Visitor Center (under 3 miles), and the Big Pine Key Flea Market (less than 3 miles).
The two-bedroom, two-bathroom house sleeps seven and boasts a fully equipped kitchen, Jacuzzi, fitness center, terrace, and free Wi-Fi, plus barbecue grills for outdoor dining.
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7 - Big Pine Key, FL
9.8 66 reviews
Big Pine Key, FL
12/01 – 12/04
$404/nighttotal: $1212 (3 )

New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7

1 1
apartment , Big Pine Key
This Big Pine Key apartment is located near Old Wooden Bridge Marina, a popular spot for fishing and boating. The apartment offers stunning views of the marina and surrounding area.
The apartment is a duplex unit with two bedrooms and can accommodate up to six guests. It comes equipped with modern amenities such as central AC, a dishwasher, and brand new furnishings, making it ideal for families or groups of friends.
Ocean Breeze House - Sleeps 8 - Escape The Cold; Our Pool Is Heated! - Big Pine Key, FL
9.4 32 reviews
Big Pine Key, FL
12/30 – 01/03
$514/nighttotal: $2056 (4 )

Ocean Breeze House - Sleeps 8 - Escape The Cold; Our Pool Is Heated!

2 8
cottage , Cudjoe Key
This Summerland Key vacation home is less than 1.2 miles from Florida Keys beaches, Crab Key, and Pye Key, offering easy access to water activities and located within 6 miles of Coupon Bight Aquatic Preserve and Venture Out Keys.
This 1500-square-foot rental boasts two bedrooms, two bathrooms, sleeps eight guests, and includes a private pool, terrace, free Wi-Fi, a fully equipped kitchen, in-unit laundry, and an on-site arcade.
Waterfront Beach House With Dock & Heated Pool! - Big Pine Key, FL
10 1 review
Big Pine Key, FL
10/13 – 10/15
$1155/nighttotal: $2310 (2 )

Waterfront Beach House With Dock & Heated Pool!

4 3
apartment , Big Pine Key
This waterfront home, located in Summerland Key at mile marker 28.5, offers easy access to Big Pine Key's attractions, including the Blue Hole trails and Kiki's Sandbar Restaurant, a short drive away.
This 2,000-square-foot vacation rental boasts four bedrooms, three bathrooms, sleeps eight, and features a private dock, heated pool with ocean views, and a fully equipped kitchen, plus amenities like beach chairs and BBQ grills.
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