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

Top-Rated Oceanfront Lodgings in Big Pine Key, FL

Plan a refreshing beach-town holiday at these seaside accommodations in Big Pine Key, FL, located just a short distance from popular coastal attractions.

Tree Top Paradise - Big Pine Key, FL
9.5 104 reviews

Tree Top Paradise

apartment, Cudjoe Key
This family-friendly vacation home is located in Summerland Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, with Florida Keys Beaches located a short drive away. This property has received excellent ratings for user experience, location, and cleanliness.
This 2-bedroom, 2-bathroom home offers 860 square feet of space and can comfortably accommodate up to 6 guests. Enjoy amenities like a private pool, a hot tub, and a game room, perfect for relaxation and entertainment.

Best family friendly Big Pine Key, FL lodging

Among the 548 accommodations in Big Pine Key, FL, here are the 4 best for families

Open Water View From Porch , Golf Cart, Dock, Bikes, Kayaks, Trailer Parking - Big Pine Key, FL
9.8 141 reviews

Open Water View From Porch , Golf Cart, Dock, Bikes, Kayaks, Trailer Parking

apartment, Cudjoe Key
This waterfront vacation home is located in Cudjoe Key, Florida, just a short walk from Venture Key, Venture Out Keys, and Out Key, and within six miles of Upper Sugarloaf Key and Florida Keys Beaches.
The 870-square-foot house features two bedrooms, one bathroom, a sofa bed, and can accommodate up to four guests, offering a comfortable and convenient space with amenities like a private pool, spa, tennis court, and a fully equipped kitchen.
Wonderful Chalet, With Terrace & Private Patio  20 Miles From Key West. - Big Pine Key, FL
10 45 reviews

Wonderful Chalet, With Terrace & Private Patio 20 Miles From Key West.

cottage, Cudjoe Key
This smoke-free cottage is located in Summerland Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, and less than four miles from Florida Keys Beaches. This "Little Gem In Paradise" is rated excellent by guests and offers a peaceful garden setting perfect for relaxing.
This one-bedroom, one-bathroom cottage can accommodate up to four guests and features a private garden, terrace, and patio. Enjoy amenities like a fully equipped kitchen, washer/dryer, free WiFi, a swimming pool, a tennis court, and barbecue grills.
Powell Family Resort - Big Pine Key, FL
9.7 42 reviews

Powell Family Resort

apartment, Big Pine Key
This Big Pine Key apartment is situated on a private 2.5-acre estate with direct access to the water and deep water dockage, offering tranquility and privacy. It has earned excellent ratings for location, cleanliness, and user experience.
This spacious rental sleeps up to 10 guests and includes a kitchen with a fridge, microwave, and dishwasher. Enjoy the private beach, Tiki bar, outdoor grill, enclosed porches, outdoor shower, kayaks, paddle boards, and more.
Pelican's Roost, Waterfront Comfort At Venture Out - Big Pine Key, FL
8.9 23 reviews

Pelican's Roost, Waterfront Comfort At Venture Out

house, Cudjoe Key
This beachfront vacation home in Cudjoe Key is a short drive from both the Ernest Hemingway Home and Museum and Duval Street in Key West, both approximately 23 miles away.
The 860 square foot house boasts two bedrooms, two bathrooms, and can accommodate up to nine guests, offering amenities such as a private pool, hot tub, fitness center, tennis court, and a private beach area.

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.

Popular destinations

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.

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Big Pine Key, FL
8.6 84 reviews

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West

cottage, Cudjoe Key
This waterfront cottage is located on Cudjoe Key, just a short drive from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offering easy access to popular attractions and activities. It has received very good user ratings, making it a popular choice for travelers.
The cottage has two bedrooms and one bathroom, providing comfortable accommodations for up to four guests. It features a fully equipped kitchen, a private pool, a terrace, a garden, and laundry facilities for a convenient and enjoyable stay.
Turtle Cove Views At Venture Out - Big Pine Key, FL
9.7 128 reviews

Turtle Cove Views At Venture Out

apartment, Cudjoe Key
This charming cottage is located on Cudjoe Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to fishing, snorkeling, and the beautiful Florida Keys scenery. The cottage consistently receives excellent ratings for location, cleanliness, and overall user experience.
The 850-square-foot cottage comfortably sleeps up to 6 guests in its two bedrooms and two bathrooms. Enjoy a relaxing vacation with amenities like a private pool, spa, and tennis court, along with a fully equipped kitchen, barbecue grills, and a spacious terrace.
Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Big Pine Key, FL
9.0 64 reviews

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West

cottage, Cudjoe Key
This waterfront cottage is located in Cudjoe Key, just a short distance from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offering a peaceful and laid-back atmosphere. Guests consistently rate this property as excellent. This two-bedroom, one-bathroom cottage offers 750 square feet of space, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, a private garden, a swimming pool, and a barbecue grill, perfect for enjoying the Florida Keys lifestyle.
Tropical Island Paradise W / Open Water Views! - Big Pine Key, FL
9.6 110 reviews

Tropical Island Paradise W / Open Water Views!

apartment, Cudjoe Key
This waterfront vacation home, located in Summerland Key near Cudjoe Key, offers easy access to Marathon and Key West.
The 820-square-foot house features two bedrooms, two bathrooms, sleeps six, and includes a private pool, spa, tennis court, and direct waterfront access with a dock, perfect for boating, fishing, and exploring nearby attractions like Coupon Bight Aquatic Preserve and Big Munson Island.

Neighborhoods and points of interest in Big Pine Key, FL

Best Big Pine Key, FL accommodation with a kitchen

Waterfront Cozy Cottage With Boat Ramp & Dock! - Big Pine Key, FL
9.9 249 reviews

Waterfront Cozy Cottage With Boat Ramp & Dock!

apartment, Big Pine Key
This waterfront cottage is located in Big Pine Key, just a short drive from the Big Pine Key Flea Market and the National Key Deer Refuge Visitor Center. It has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms, one bathroom, and can accommodate up to six guests. It offers a fully equipped kitchen, a private patio, a spa, free Wi-Fi, and a smoke-free environment.
Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Big Pine Key, FL
8.6 98 reviews

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West

cottage, Cudjoe Key
This charming cottage is situated in Summerland Key, just a short drive from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offering a peaceful retreat in the Florida Keys. It has received excellent ratings from previous guests, making it a popular choice for travelers. This cozy cabin provides 750 square feet of space, comfortably accommodating up to four guests in its two bedrooms and one bathroom. Enjoy a refreshing dip in the private pool, grill up a meal on the barbecue, and stay connected with free Wi-Fi.
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7 - Big Pine Key, FL
9.8 68 reviews

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

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.
Palm Cottage - Sleeps 4  Summer Fun ..Lobster Season. - Big Pine Key, FL
9.8 55 reviews

Palm Cottage - Sleeps 4 Summer Fun ..Lobster Season.

cottage, Cudjoe Key
Palm Cottage, a pet-friendly Summerland Key vacation home, is located less than a mile from Florida Keys Beaches, Crab Key, and Pye Key, offering easy access to swimming, sunbathing, and exploring the natural beauty of the Keys.
This 480-square-foot cottage features two bedrooms, one bathroom, and accommodates four guests, providing a private patio, fully equipped kitchen, free Wi-Fi, and access to a shared pool and barbecue grills.

Best Big Pine Key, FL accommodation with a balcony

Reel Island Retreat #273 At Venture Out In The Florida Keys - Big Pine Key, FL
8.6 9 reviews

Reel Island Retreat #273 At Venture Out In The Florida Keys

apartment, Cudjoe Key
Sunny Escape - Venture Out Unit 128 - Big Pine Key, FL
9.8 6 reviews

Sunny Escape - Venture Out Unit 128

apartment, Cudjoe Key
Bright 2br 2ba In Cudjoe Key| Sleeps 6 | Wifi | Washer Dryer | Near Water & Key West - Big Pine Key, FL
No reviews

Bright 2br 2ba In Cudjoe Key| Sleeps 6 | Wifi | Washer Dryer | Near Water & Key West

apartment, Cudjoe Key
3 Night Minimum! Spectacular Ocean Views! - Big Pine Key, FL
8.6 29 reviews

3 Night Minimum! Spectacular Ocean Views!

apartment, Cudjoe Key

Compare 5-Star Accommodations in Big Pine Key, FL

Luxury lodging in Big Pine Key, FL elevates your stay with refined service, premium amenities, and a perfectly situated home base.

Island Therapy - Big Pine Key, FL
9.8 67 reviews

Island Therapy

apartment, Cudjoe Key

Browse Dog-Friendly Accommodations in Big Pine Key, FL

A quality pet-friendly lodging in Big Pine Key, FL means dog-friendly beaches and outdoor washing facilities are always part of the package.

Parmer's Resort - Big Pine Key, FL
8.9 1607 reviews

Parmer's Resort

resort, Big Pine Key
Old Wooden Bridge Resort & Marina - Big Pine Key, FL
8.5 889 reviews

Old Wooden Bridge Resort & Marina

house, Big Pine Key
Waterfront 2br W/ Dock & Pool Access - Big Pine Key, FL
9.4 58 reviews

Waterfront 2br W/ Dock & Pool Access

apartment, Cudjoe Key
2 Bedroom Aqualodge # 11 Grouper - Big Pine Key, FL
9.4 345 reviews

2 Bedroom Aqualodge # 11 Grouper

barge, Big Pine Key

Check Out Accommodations with On-Site Dining in Big Pine Key, FL

On-site dining featuring fresh local food comes with every of these lodgings in Big Pine Key, FL, so dinner is sorted without leaving the property.

Waterfront Haven House With Boat Basin & Ramp! - Big Pine Key, FL
9.9 145 reviews

Waterfront Haven House With Boat Basin & Ramp!

apartment, Big Pine Key
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