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Big Pine Key, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Big Pine Key, FL

Best Big Pine Key, FL vacation rentals with a balcony

Ocean View Suite Barnacle Resort - Big Pine Key, FL
Big Pine Key, FL
12/01 – 12/04
$495/nighttotal: $1485 (3 )

Ocean View Suite Barnacle Resort

1 1
apartment , Big Pine Key
This oceanfront Big Pine Key vacation rental, located in Long Beach Estates, is 6.8 miles from Bahia Honda State Park and 34 miles from Key West.
The 600-square-foot apartment features one bedroom, one bathroom, sleeps four, and includes a kitchen, private beach access, kayaks, bicycles, and a terrace; breakfast is also provided.
Bp10flr Big Pine Bungalow - Big Pine Key, FL
Big Pine Key, FL
07/25 – 08/22
$221/nighttotal: $6188 (28 )

Bp10flr Big Pine Bungalow

3 6
house , Big Pine Key
The Big Pine Bungalow in Big Pine Key offers a tranquil island escape, located 23 miles from Florida Keys Aquarium Encounters and 30 miles from the Ernest Hemingway Home and Museum and Duval Street.
This 1360 square foot home accommodates up to 13 guests with 3 bedrooms and 2 bathrooms, featuring air conditioning, a fully equipped kitchen with a dishwasher and oven, a private balcony, a garden, a tennis court, and an outdoor swimming pool.
167 M² House ∙ 4 Bedrooms ∙ 8 Guests - Big Pine Key, FL
10 6 reviews
Big Pine Key, FL
07/25 – 08/22
$267/nighttotal: $7476 (28 )

167 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 6
house , Big Pine Key
This oceanfront residence on Ramrod Key offers direct Atlantic Ocean views and immediate access to Niles Channel, a crucial passage connecting the Atlantic and Gulf in the lower Florida Keys. This 1800 sq ft vacation home accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, featuring a new heated swim/spa pool, an 85 ft concrete seawall, and nearly 70 ft of deep water dockage for boating and fishing enthusiasts.
Hibiscus House - Heated Pool - Big Pine Key, FL
Big Pine Key, FL
07/25 – 08/22
$163/nighttotal: $4564 (28 )

Hibiscus House - Heated Pool

4 6
apartment , Big Pine Key
This Big Pine Key vacation home is located near the National Key Deer Refuge, a 15-minute drive from Bahia Honda State Park and 30 minutes from Key West or Marathon.
This newly renovated four-bedroom house sleeps ten guests and boasts a heated saltwater pool, tiki hut, three-car parking, plus boat trailer parking near a boat ramp, and porches offering refuge views of the Key Deer.

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.

Dates Available Oct, Nov, Dec 2023 - Big Pine Key, FL
9.9 19 reviews
Big Pine Key, FL
07/25 – 08/22
$257/nighttotal: $7196 (28 )

Dates Available Oct, Nov, Dec 2023

2 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.
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.
3-bedroom House In Lower Keys With Hot Tub, Sleeps 10+, Pet Freindly - Big Pine Key, FL
Big Pine Key, FL
07/25 – 08/22
$435/nighttotal: $12180 (28 )

3-bedroom House In Lower Keys With Hot Tub, Sleeps 10+, Pet Freindly

3 6
apartment , Big Pine Key
This Big Pine Key waterfront home, located in the Pine Channel Estates neighborhood, offers easy access to both the Gulf of Mexico and the Atlantic Ocean, placing you near attractions like the Blue Hole and Big Munson Island.
The three-bedroom, two-bathroom house features a king bed, queen bed, two bunk beds, a 75-foot two-level dock, a hot tub, full laundry facilities, WiFi, and can comfortably accommodate up to 12 guests.

Frequently Asked Questions about vacation rentals in Big Pine Key, FL

Destinations nearby

Best Big Pine Key, FL vacation rentals with parking

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.
Waterfront Bungalow W/ Kitchen, Private Patio & Marina Views Near Snorkel Spots - Big Pine Key, FL
Big Pine Key, FL
12/01 – 12/04
$425/nighttotal: $1275 (3 )

Waterfront Bungalow W/ Kitchen, Private Patio & Marina Views Near Snorkel Spots

3 1
apartment , Big Pine Key
This waterfront vacation rental on Summerland Key is located just minutes from Looe Key Reef and Bahia Honda State Park, offering prime access to coastal activities.
This 660 sq. ft. condo accommodates up to six guests and features a kitchen, air conditioning, a shared heated pool, complimentary kayaks, paddleboards, and bikes, with pets welcome for an additional fee.

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.

1 Bedroom Aqualodge # 6 Tarpon - Big Pine Key, FL
9.5 51 reviews
Big Pine Key, FL
10/13 – 10/15
$375/nighttotal: $750 (2 )

1 Bedroom Aqualodge # 6 Tarpon

1 3
barge , Big Pine Key
This floating home is located in a tranquil area of Big Pine Key, overlooking the Bogie Channel, just a short distance from the Florida Keys Resort and Marina. It has received excellent ratings for location, cleanliness, and user experience.
The barge has one bedroom and one bathroom, accommodating up to four guests. Guests can enjoy access to resort amenities, including a swimming pool, and can explore the surrounding waterways by boat, kayak, or bike.
Fishermans Dream House - Big Pine Key, FL
Big Pine Key, FL
07/25 – 08/22
$377/nighttotal: $10556 (28 )

Fishermans Dream House

3 6
apartment , Big Pine Key
This vacation rental is situated in Big Pine Key's Eden Pines neighborhood, providing 180 feet of seawall on a secluded corner lot with convenient access to boat ramps and the Coupon Bight Aquatic Preserve.
This 3-bedroom, 2-bathroom house accommodates up to 8 guests and features an outdoor bar with an ice maker, a private pool, open decks, two living rooms, and opportunities for fishing and spotting key deer.
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.
Newly Renovated 3/2 With Pool And Canal Access!!! - Big Pine Key, FL
Big Pine Key, FL
07/25 – 08/22
$387/nighttotal: $10836 (28 )

Newly Renovated 3/2 With Pool And Canal Access!!!

3 6
apartment , Big Pine Key
This newly renovated 3-bedroom, 2-bathroom vacation home in Port Pine Heights, Big Pine Key, is located 0.2 miles from Florida Keys Beaches and near Coupon Bight Aquatic Preserve, Blue Hole, and Big Munson Island.
This waterfront retreat accommodates up to 8 guests and features air conditioning, a microwave oven, a dishwasher, a swimming pool, and parking, offering an immersive Florida Keys experience.

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.

Star Room Barnacle Resort - Big Pine Key, FL
8.8 5 reviews
Big Pine Key, FL
12/01 – 12/04
$333/nighttotal: $999 (3 )

Star Room Barnacle Resort

1 1
apartment , Big Pine Key
149 M² House ∙ 3 Bedrooms ∙ 6 Guests - Big Pine Key, FL
Big Pine Key, FL
12/01 – 12/04
$225/nighttotal: $675 (3 )

149 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 1
house , Big Pine Key
Go Fish Inn - Big Pine Key, FL
Big Pine Key, FL
10/13 – 10/15
$12061/nighttotal: $24122 (2 )

Go Fish Inn

2 3
house , Big Pine Key
Disfruta De La Sencillez De Este Alojamiento Tranquilo Y Céntrico. - Big Pine Key, FL
Big Pine Key, FL
07/25 – 08/22
$230/nighttotal: $6440 (28 )

Disfruta De La Sencillez De Este Alojamiento Tranquilo Y Céntrico.

3 6
apartment , Big Pine Key
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