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Best Vacation rentals and Airbnb offers in Big Pine Key, FL
10 11 reviews
Big Pine Key, FL
10/13 – 10/15
$1119/nighttotal: $2238 (2 )
Waterfront Beach House With Dock & Heated Pool!
1 3
apartment , Big Pine Key
This Big Pine Key waterfront home boasts a 200-foot private dock, direct ocean access, and proximity to Little Torch Key's boat ramp. The four-bedroom, three-bathroom house sleeps eight, features a heated pool with ocean views, a full kitchen, washer/dryer, BBQ grills, and ample parking for your Big Pine Key vacation.
9.9 142 reviews
Big Pine Key, FL
10/13 – 10/15
$666/nighttotal: $1332 (2 )
Waterfront Haven House With Boat Basin & Ramp!
1 3
apartment , Big Pine Key
This waterfront property, located in Little Torch Key near the intersection of State Road 4A, offers easy boat access via a private ramp and is close to Big Pine Key's fishing and snorkeling opportunities. The 1120-square-foot houseboat, accommodating up to eight guests, features three bedrooms, a full kitchen with modern appliances, a spa, and a private boat basin with a 50-foot boat ramp; additional amenities include beach chairs, a BBQ grill, and smart TVs.
9.0 209 reviews
Big Pine Key, FL
10/13 – 10/15
$983/nighttotal: $1966 (2 )
Ocean Front Paradise/290 Ft Private Dock/awesome Views
1 3
apartment , Big Pine Key
This oceanfront apartment on Big Pine Key is located just 3 minutes from Winn Dixie and a short boat ride from Picnic Island, Looe Key Reef, and the Key Deer National Wildlife Preserve. The property has received excellent ratings for location, cleanliness, and user experience. The apartment can be rented as a whole house with 3 bedrooms and 2 bathrooms, or just the downstairs unit with 2 bedrooms and 1 bathroom, accommodating up to 8 guests. The home offers a private dock, a spacious garden, a spa, a fitness center, a terrace, a large parking lot, a fully equipped kitchen, and a washer and dryer.
9.6 257 reviews
Big Pine Key, FL
10/13 – 10/15
$315/nighttotal: $630 (2 )
Tiny House | 35 Min To Kw + Free Parking & Pool
1 3
house , Big Pine Key
This cozy home is located in the Breezy Pines RV Resort in Big Pine Key, just a short drive from the beach and a quick trip to Key West's attractions. The house has received excellent ratings for location, cleanliness, and overall experience. This tiny house has two bedrooms and accommodates up to four guests, making it perfect for families or small groups. Enjoy the Florida sunshine on the patio with a grill, relax by the pool, and take advantage of the fully equipped kitchen, laundry facilities, and free parking.
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.
9.7 13 reviews
Big Pine Key, FL
10/13 – 10/15
$525/nighttotal: $1050 (2 )
Keys Beach Retreat Close To Key West
1 3
apartment , Big Pine Key
This Big Pine Key condo offers a prime location, situated 3 miles from Bahia Honda Beach and 27 miles from Key West, with close proximity to the National Key Deer Refuge and Looe Key Reef. This 3-bedroom, 2-bathroom vacation rental accommodates up to 11 guests and features a full kitchen, air conditioning, garden, and parking, making it ideal for exploring the Florida Keys' natural attractions and fishing spots.
9.9 63 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.
8.8 2133 reviews
Big Pine Key, FL
10/13 – 10/15
$242/nighttotal: $484 (2 )
Parmer's Resort
1 3
resort , Big Pine Key
Parmer's Resort is located in Little Torch Key, just a short drive from the Florida Keys Aquarium Encounters and about 30 miles from Key West. The resort has received very good ratings for its cleanliness, user experience, and excellent location. The resort offers a peaceful escape from the hustle and bustle of Key West while still being close to attractions. Guests can enjoy a variety of amenities, including a swimming pool, a garden, a bar, a fitness center, and a grill, as well as fishing opportunities and a continental breakfast.
9.2 99 reviews
Big Pine Key, FL
10/13 – 10/15
$313/nighttotal: $626 (2 )
2 Bedroom Pink Cabin Half/duplex # 11
2 3
cabin , Big Pine Key
This Big Pine Key cabin offers a tranquil escape, just a short drive from the island's best beaches and attractions. It consistently receives excellent ratings for its cleanliness, location, and overall experience. The two-bedroom, one-bathroom cabin comfortably accommodates up to seven guests. Enjoy a fully equipped kitchen, air conditioning, a private pool, and a lush garden perfect for relaxing and enjoying the peaceful surroundings.
9.8 66 reviews
Big Pine Key, FL
10/13 – 10/15
$442/nighttotal: $884 (2 )
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7
1 3
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.
8.8 105 reviews
Big Pine Key, FL
10/13 – 10/15
$313/nighttotal: $626 (2 )
1 Bedroom Cabin Half/duplex Unit A Up On Stilts
1 3
apartment , Big Pine Key
This apartment is situated at the Old Wooden Bridge Resort and Marina in Big Pine Key, Florida, just a short distance from the famous Looe Key Reef. The apartment has a very good user rating, and excellent location and cleanliness ratings. The apartment has two full-size beds in the bedroom and a queen sofa sleeper in the living room, comfortably accommodating up to four guests. The apartment features a shared deck, a saltwater pool, boat rentals, pet-friendly accommodations, and convenient parking.
9.4 14 reviews
Big Pine Key, FL
10/13 – 10/15
$225/nighttotal: $450 (2 )
Airstream Flying Cloud
1 3
apartment , Big Pine Key
This Airstream travel trailer is located in Big Pine Key, a short drive from Bahia Honda State Park, offering a peaceful escape from the hustle and bustle of larger cities. The trailer has received excellent ratings for location, cleanliness, and user experience. The Airstream comfortably sleeps four guests in a cozy space with a queen bed and convertible couch. Amenities include a fully equipped kitchen, two air conditioning units, and parking, allowing you to explore the island's natural beauty and enjoy the tranquil atmosphere.
Best Big Pine Key, FL vacation rentals with a balcony
8.0 48 reviews
Big Pine Key, FL
10/13 – 10/15
$447/nighttotal: $894 (2 )
Barnacle Resort
1 3
resort , Big Pine Key
Barnacle Resort, a beachfront bed and breakfast in Big Pine Key's Long Beach Estates, offers easy access to Coupon Bight Aquatic Preserve and is within a 15-minute drive of Newfound Harbor Keys and Cook Island. This lodging provides guests with free continental breakfast, free WiFi in public areas, free self-parking, free bicycle use, a rooftop terrace with scenic views, and gas grills for guest use.
8.5 767 reviews
Big Pine Key, FL
10/13 – 10/15
$264/nighttotal: $528 (2 )
Old Wooden Bridge Resort & Marina
1 3
house , Big Pine Key
This house is located in Big Pine Key, just 25 miles from Florida Keys Aquarium Encounters and 15 miles from Seven Mile Bridge, offering easy access to the area's attractions. Guests have consistently rated the house very good for cleanliness and excellent for location. The house features a kitchen with a fridge, microwave oven, and dishwasher, as well as a swimming pool, terrace, and garden. Guests can enjoy stunning sea views, take advantage of free Wi-Fi, and relax on the sun terrace.
9.6 105 reviews
Big Pine Key, FL
10/13 – 10/15
$681/nighttotal: $1362 (2 )
Old Florida Style, Wrap Around Porch, Boat Basin For Dockage, Open Water
3 3
apartment , Big Pine Key
This waterfront Big Pine Key vacation home boasts stunning views and direct water access, situated within three miles of Florida Keys Beaches and the Big Pine Key Flea Market, and six miles from the Key West Visitor Center. This 1700-square-foot house features three bedrooms, two bathrooms, and accommodates six guests, offering a fully equipped kitchen, in-house laundry, and a terrace—perfect for enjoying the Key's natural beauty.
8.4 12 reviews
Big Pine Key, FL
10/13 – 10/15
$599/nighttotal: $1198 (2 )
Charming 3-bedroom House In \Nbig Pine Key Near Beach And Key West
3 3
apartment , Big Pine Key
This 3-bedroom, 2-bathroom vacation home is located in the Sands district of Big Pine Key, a short walk to the Key West Visitors Center and Coupon Bight Aquatic Preserve. This pet-friendly apartment accommodates up to 11 guests with a fully equipped kitchen, in-unit washer/dryer, complimentary Wi-Fi, and on-site parking, offering easy access to attractions like Plages de l’archipel des Keys and Blue Hole.
Our Favorite Family-Friendly Vacation Rentals in Big Pine Key, FL
Find the perfect family vacation rental or Airbnb in Big Pine Key, FL with plenty of room to spread out near local beaches.
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.
9.9 103 reviews
Big Pine Key, FL
10/13 – 10/15
$356/nighttotal: $712 (2 )
Tiny Fish Haus
1 3
cabin , Big Pine Key
This Big Pine Key vacation home is located in a quiet RV park, just a short drive from the main Key West attractions and across the highway from an oceanfront park. The property has earned excellent ratings for location, cleanliness, and overall user experience. This two-bedroom, one-bathroom home can comfortably sleep up to four guests. It offers modern amenities like Wi-Fi, Alexa, and a mini washing machine, along with an outdoor patio featuring a sink, black stone grill, and an outdoor shower.
Frequently Asked Questions about vacation rentals in Big Pine Key, FL
What sports or outdoor activites can visitors enjoy in and around Big Pine Key, FL?
Fishing is definitely king here, with great spots for both inshore and offshore fishing. You can also go kayaking, paddleboarding, or windsurfing in the calm waters. For the adventurous, there's scuba diving and snorkeling, with amazing coral reefs and marine life just off the coast.
What are the best Airbnb and vacation rentals in Big Pine Key, FL?
What other towns or cities can be easily accessed from Big Pine Key, FL?
You can easily drive to Marathon, which is about 15 minutes away and has a lot of shops and restaurants. Key West is about an hour and a half drive, and offers a lot of attractions and nightlife. If you want to explore the mainland, Miami is about a 3-hour drive.
What are the most popular Airbnbs in Big Pine Key, FL?
What amenities are commonly available in vacation rentals in Big Pine Key, FL?
Most vacation rentals in Big Pine Key come with basic amenities like air conditioning, Wi-Fi, and a fully equipped kitchen. Many also have private pools, hot tubs, and laundry facilities. You can find rentals with boats, kayaks, or paddleboards for exploring the waters.
What are the best vacation rentals with a pool in Big Pine Key, FL?
What time of year is best to rent a vacation rental 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 with little rain. The summer months can be hot and humid with occasional storms.
What are the best rentals for families and kids in Big Pine Key, FL?
What are the local dishes in Big Pine Key, FL region?
Fresh seafood is a big part of the local cuisine, with conch fritters, stone crab claws, and grouper sandwiches being popular choices. You can also find some great Key lime pie, a sweet and tangy treat that is a must-try while you're here.
What are the best rentals or Airbnbs with a jacuzzi in Big Pine Key, FL?
Best Big Pine Key, FL vacation rentals with parking
8.5 15 reviews
Big Pine Key, FL
10/13 – 10/15
$505/nighttotal: $1010 (2 )
Ocean View Room At Barnacle Resort
1 3
studio , Big Pine Key
Ocean View Room at Barnacle Resort, a beachfront vacation home in Big Pine Key, Florida, is located 15 miles from the Seven Mile Bridge and 22 miles from Florida Keys Aquarium Encounters. This 600-square-foot rental boasts one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchenette, free Wi-Fi, a private patio, and access to a garden.
9.9 129 reviews
Big Pine Key, FL
10/13 – 10/15
$1076/nighttotal: $2152 (2 )
Waterfront Anchor House With Boat Basin & Ramp!
4 3
apartment , Big Pine Key
This Big Pine Key apartment is located just steps from the ocean and a short distance from the Little Torch Key boat ramp, offering easy access to both the beach and boating adventures. The property has received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay. The spacious 1430 square foot apartment can comfortably accommodate up to 10 guests in its four bedrooms and two bathrooms. Enjoy a fully equipped kitchen, laundry facilities, a private boat basin and ramp, a patio with BBQ grill, and plenty of space for outdoor activities, making it perfect for families or groups.
8.6 4 reviews
Big Pine Key, FL
10/13 – 10/15
$624/nighttotal: $1248 (2 )
Treehouse Private Village Barnacle Resort
1 3
cabin , Big Pine Key
This beachfront cottage in Long Beach Estates, Big Pine Key offers easy access to Florida Keys Beaches and Coupon Bight Aquatic Preserve, with Big Munson Island and Blue Hole also nearby. The 700-square-foot home features one bedroom, one bathroom, sleeps four, and includes a kitchen, air conditioning, a terrace, a garden, parking, internet, and complimentary kayaks and bicycles.
Big Pine Key, FL
10/13 – 10/15
$242/nighttotal: $484 (2 )
Parmer's Resort
1 3
resort , Big Pine Key
Parmer's Resort is located in Summerland Key, just a short drive from the charming downtown area of Big Pine Key. The resort offers a convenient location for exploring the island's attractions, restaurants, and shops. The resort offers a variety of amenities for a comfortable stay, including a picnic area, barbecue facilities, and free Wi-Fi. Guests can also enjoy laundry and concierge services, as well as the option of connecting rooms.
Neighborhoods and points of interest in Big Pine Key, FL
Search Vacation Rentals with Swimming Pool in Big Pine Key, FL
Complement your time by the water with a dip in the pool at these Big Pine Key, FL vacation rentals with on-site swimming facilities.
9.5 105 reviews
Big Pine Key, FL
10/13 – 10/15
$375/nighttotal: $750 (2 )
2 Bedroom Aqualodge # 13 Barracuda
1 3
barge , Big Pine Key
This barge is located at the Old Wooden Bridge Resort and Marina in Big Pine Key, just a short distance from the beautiful saltwater pool and fish cleaning stations. It has received excellent ratings for its location, cleanliness, and overall user experience. This charming vessel features two bedrooms and can comfortably accommodate up to six guests. The barge offers a kitchen with a fridge and microwave, air conditioning, a swimming pool, a garden, parking, and internet access.
9.9 160 reviews
Big Pine Key, FL
10/13 – 10/15
$2156/nighttotal: $4312 (2 )
Waterfront Beach Houses With Dock & Heated Pool!
1 3
apartment , Big Pine Key
This Big Pine Key waterfront home is located 2.3 miles from the Big Pine Key Flea Market and 2.4 miles from the National Key Deer Refuge Visitor Center, offering easy access to local attractions and wildlife viewing. This 3400-square-foot vacation rental boasts eight bedrooms, five bathrooms, a private pool, and a fully equipped kitchen, comfortably accommodating large groups with amenities including free Wi-Fi, a DVD player, and outdoor barbecue grills.
9.3 26 reviews
Big Pine Key, FL
10/13 – 10/15
$305/nighttotal: $610 (2 )
Rv In The Keys | Tropical Retreat
1 3
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.
8.7 17 reviews
Big Pine Key, FL
10/13 – 10/15
$330/nighttotal: $660 (2 )
2 Bedroom Pink Cabin Half/duplex # 10
1 3
cabin , Big Pine Key
This cozy cabin is located at the Old Wooden Bridge Resort and Marina in Big Pine Key, Florida, just a short drive from Bahia Honda State Park and the Seven Mile Bridge. The cabin has received very good user ratings, an excellent location rating, and a very good cleanliness rating. The cabin features two bedrooms and one bathroom, comfortably accommodating up to seven guests. Enjoy access to a full kitchen, a living room, a swimming pool, a garden, and parking. You also have full access to the resort's amenities, including the marina and other recreational facilities.
Search Coastal Vacation Rentals near Big Pine Key, FL
Discover charming seaside vacation rentals in Big Pine Key, FL near the coast. Browse our favorite coastal picks to find your perfect beach-town match.
10 6 reviews
Big Pine Key, FL
10/13 – 10/15
$408/nighttotal: $816 (2 )
2 Bedroom Aqua Lodge # 15 Porgie
1 3
boat , Big Pine Key
9.6 99 reviews
Big Pine Key, FL
10/13 – 10/15
$442/nighttotal: $884 (2 )
New Deluxe Duplex Unit, 2 Queen Beds, Unit G-4
1 3
apartment , Big Pine Key
Big Pine Key, FL
10/13 – 10/15
$684/nighttotal: $1368 (2 )
Ocean View Suite Barnacle Resort
1 3
apartment , Big Pine Key
9.1 9 reviews
Big Pine Key, FL
10/13 – 10/15
$351/nighttotal: $702 (2 )
1 Bedroom Floating Cabin # 3 Hogfish
1 3
barge , Big Pine Key
Browse Luxury Vacation Rentals in Big Pine Key, FL
Premium waterfront rentals in Big Pine Key, FL combine upscale design with refined service for a truly superior getaway.
9.4 62 reviews
Big Pine Key, FL
10/13 – 10/15
$325/nighttotal: $650 (2 )
1 Bedroom Floating Cabin # 9 Hammerhead
1 3
barge , Big Pine Key
Choose the Right Vacation Rentals with a Steam Room in Big Pine Key, FL
Elevate your wellness routine with a vacation rental featuring a sauna in Big Pine Key, FL , ideal for a restorative end to your day.