Vacation Rentals in Big Pine Key, FL

478 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Big Pine Key, FL vacation rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

478 Vacation rentals and Airbnb in Big Pine Key, FL

Best family friendly Big Pine Key, FL vacation rentals

Among the 478 accommodations in Big Pine Key, FL, here are the 4 best family friendly rentals

Parmer's Resort - Big Pine Key, FL
8.9 1610 reviews

Parmer's Resort

resort, Big Pine Key
Parmer's Resort is situated in Little Torch Key, just a short drive from the Florida Keys Aquarium Encounters and other popular attractions in Key West. It’s a peaceful retreat, offering a tranquil escape from the hustle and bustle of the city. The resort has received very good user ratings across the board, with guests particularly praising its excellent location and cleanliness.
The accommodation features a shared lounge, an outdoor swimming pool and a garden. Guests can enjoy a continental breakfast each morning and make use of the on-site grill to prepare their own meals. There's also a fitness centre, a bar, free Wi-Fi and a concierge service.
Ocean Front Paradise/ Private Dock/awesome Views - Big Pine Key, FL
9.0 213 reviews

Ocean Front Paradise/ Private Dock/awesome Views

apartment, Big Pine Key
This apartment is situated on Big Pine Key, just 3km from Winn Dixie grocery store and a short drive from the Key Deer National Wildlife Refuge and Bahia Honda State Park. The apartment has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
The apartment has two separate units, accommodating up to 8 guests. It boasts a private dock with mooring, a fish cleaning station, and a picnic island, perfect for enjoying the area's fishing and diving opportunities.
Old Wooden Bridge Resort & Marina - Big Pine Key, FL
8.4 906 reviews

Old Wooden Bridge Resort & Marina

house, Big Pine Key
This property is located in Big Pine Key, just 25 miles from Florida Keys Aquarium Encounters and 15 miles from Seven Mile Bridge, offering a peaceful escape with easy access to local attractions. The house has received very good user ratings for its cleanliness and overall experience, and the location has been rated excellent.
The accommodation features a fully equipped kitchen, a private bathroom, and a terrace or balcony. Guests can enjoy the swimming pool, the garden, and the bar, as well as free Wi-Fi, parking, and a grill for outdoor cooking.
Conch House - Ocean Front With Dock And Pool - Big Pine Key, FL
10 44 reviews

Conch House - Ocean Front With Dock And Pool

apartment, Big Pine Key
This waterfront property in Big Pine Key is conveniently located just 4km from the Big Pine Key Flea Market and 4.2km from the National Key Deer Refuge Visitor Center, making it a great base for exploring the area. The house has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This four-bedroom, four-bathroom home can comfortably accommodate up to eight guests. The property offers a range of amenities, including a private pool, a spacious terrace, a fully equipped kitchen, and a barbecue grill, perfect for enjoying the Florida sunshine and creating lasting memories.

Best Big Pine Key, FL vacation rentals with a pool

Among the 478 accommodations in Big Pine Key, FL, here are the 4 best rentals with a pool

Rv In The Keys | Tropical Retreat - Big Pine Key, FL
9.4 28 reviews

Rv In The Keys | Tropical Retreat

cabin, Big Pine Key
This Big Pine Key motorhome rental, ‘Rv In The Keys | Inside/outside Living W/patio’, is situated in a convenient RV park, approximately 48km from Key West and 32km from Marathon, offering easy access to both destinations.
The 1-bedroom, 1-bathroom mobile home sleeps four guests, features a fully equipped kitchen, two TVs, air conditioning, and access to an on-site swimming pool, garden, and laundry facilities; its unique design allows for indoor/outdoor living via a convertible patio area.
Private Island - The True Privilege Of Seclusion - Big Pine Key, FL
No reviews

Private Island - The True Privilege Of Seclusion

apartment, Big Pine Key
This exclusive eco-luxury villa offers a rare private island experience, accessible only by boat, situated approximately 24 to 32 kilometres from the mainland of Big Pine Key.
This secluded accommodation, perfect for romantic retreats and creative getaways, accommodates up to eight guests with three bedrooms, two bathrooms, and features direct beachfront access, solar power, and all essential amenities including air conditioning and WiFi.
New Deluxe Duplex Unit, 2 Queen Beds, Unit J-7 - Big Pine Key, FL
9.8 69 reviews

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

apartment, Big Pine Key
This apartment is located just a short distance from Old Wooden Bridge Marina, offering stunning views of the waterfront and easy access to Big Pine Key's attractions. The surrounding area is peaceful and provides a relaxing atmosphere for your stay.
This modern flat is ideal for groups of up to six people and features a well-equipped kitchen with a fridge, microwave, and dishwasher. Amenities include air conditioning, a swimming pool, a garden, and parking.
2 Bedroom Aqualodge # 14 Yellowtail - Big Pine Key, FL
9.8 12 reviews

2 Bedroom Aqualodge # 14 Yellowtail

boat, Big Pine Key
This brand-new houseboat, situated at Old Wooden Bridge Marina in Big Pine Key, Florida, offers convenient access to resort amenities.
The one-bedroom, one-bathroom vessel sleeps six guests and boasts a kitchen, air conditioning, and internet access, plus the unique experience of staying on a houseboat with swimming pool and parking.

Frequently asked questions about holiday rentals in Big Pine Key, FL

  • What are some interesting places to visit in or near Big Pine Key, FL?

    Big Pine Key is a beautiful island with a laid-back vibe. You can visit the National Key Deer Refuge, where you can see the endangered Key deer. The Bahia Honda State Park is a great spot for swimming, fishing, and camping. Just a short drive away, you can explore the historic Old Seven Mile Bridge, offering stunning views.
  • What are the best Airbnb and vacation rentals in Big Pine Key, FL?

    Old Wooden Bridge Resort & Marina, Waterfront Beach House With Dock & Heated Pool and Cheerful Tiny House In The Florida Keys are the most popular Airbnb and vacation rentals in Big Pine Key, FL among travelers.

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

    The best walking or cycling route is definitely the Big Pine Key Loop Road. It's a scenic 10km loop that takes you past the beautiful beaches, mangrove forests, and the historic Old Seven Mile Bridge. You can also explore the National Key Deer Refuge on foot or by bike, keeping an eye out for the adorable Key deer.
  • What are the most popular Airbnbs in Big Pine Key, FL?

  • What sports or outdoor activites can visitors enjoy in and around Big Pine Key, FL?

    Big Pine Key is a paradise for outdoor enthusiasts. You can enjoy swimming, sunbathing, and kayaking at the beautiful beaches. Fishing is a popular activity, with plenty of charter boats available. For those seeking adventure, there's scuba diving and snorkeling at the nearby Looe Key Reef, known for its vibrant coral and marine life.
  • What are the best vacation rentals with a pool in Big Pine Key, FL?

  • What other towns or cities can be easily accessed from Big Pine Key, FL?

    Big Pine Key is part of the Florida Keys, a chain of islands connected by bridges. You can easily drive to the nearby towns of Marathon, Islamorada, and Key West. Marathon is known for its fishing and dolphin watching, while Islamorada is a popular spot for boating and watersports. Key West is the southernmost point of the US and offers a vibrant nightlife and historical attractions.
  • What are the best rentals for families and kids in Big Pine Key, FL?

  • What amenities are commonly available in vacation rentals in Big Pine Key, FL?

    Vacation rentals in Big Pine Key usually offer a range of amenities to make your stay comfortable. Most properties include air conditioning, Wi-Fi, and a fully equipped kitchen. You can also find rentals with private pools, hot tubs, and outdoor grills. Some rentals even offer kayaks or paddleboards for exploring the surrounding waters.
  • What are the best rentals or Airbnbs with a jacuzzi 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. This is also the peak season, so expect higher prices and more crowds. If you prefer a quieter and more affordable trip, consider visiting during the shoulder seasons, from April to June or September to November.
  • What are the local dishes in Big Pine Key, FL region?

    The local cuisine in the Florida Keys is a mix of Caribbean and American influences. Some popular dishes include fresh seafood like conch fritters, stone crab claws, and Key lime pie. You can also find delicious Cuban sandwiches and other Latin American specialties. Don't forget to try the local Key lime juice, a refreshing and tart drink made from the famous Key lime.

Popular destinations

Best Big Pine Key, FL holiday rentals with a balcony

Beach View Room Dormitory Room Barnacle Resort - Big Pine Key, FL
No reviews

Beach View Room Dormitory Room Barnacle Resort

apartment, Big Pine Key
This oceanfront apartment in Long Beach Estates, Big Pine Key, is situated 11km from Bahia Honda State Park and 55km from Key West.
The 46-square-metre self-catering flat offers one bedroom, one bathroom, sleeps two, and includes a private terrace, garden access, parking, Wi-Fi, and complimentary kayaks and bicycles; guests can also enjoy nearby restaurants and explore Coupon Bight Aquatic Preserve.
Treehouse Private Village Barnacle Resort - Big Pine Key, FL
8.6 4 reviews

Treehouse Private Village Barnacle Resort

cabin, Big Pine Key
This beachfront cottage in Long Beach Estates, Big Pine Key, offers easy access to Coupon Bight Aquatic Preserve and is near Big Munson Island and Blue Hole.
The 65 square metre (700 square foot) property sleeps four, boasting a bedroom, bathroom, kitchen with fridge, air conditioning, Wi-Fi, a terrace, garden, parking, and complimentary kayaks and bicycles.
Frigate's Nest Extraordinary 8bed/8bath Nightly Rental With Dockage & Private Pool - Big Pine Key, FL
8.8 6 reviews

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

apartment, Big Pine Key
This waterfront residence is located in Little Torch Key, approximately 4.8 kilometres from Looe Key Reef and a short drive from the lower Florida Keys' islands.
This exclusive eight-bedroom, eight-bathroom holiday home accommodates sixteen guests and features a private pool, dockage for boats up to 10.6 metres, and kayaks, offering direct open water views.

Best Big Pine Key, FL holiday rentals with parking

Tranquility Bayview House-ocean Front With Pool, Boat Basin And Boat Ramp - Big Pine Key, FL
10 13 reviews

Tranquility Bayview House-ocean Front With Pool, Boat Basin And Boat Ramp

apartment, Big Pine Key
This waterfront vessel, located on Little Torch Key at mile marker 28.5, offers direct access to the Gulf and Atlantic, situated approximately 5.6 kilometres by road from Big Pine Key's Blue Hole trails and key deer habitat.
This pet-friendly accommodation sleeps ten guests and boasts a 36-foot boat capacity with a dedicated boat basin, ramp, water hose, and catch cleaning station, plus walking distance to Kiki's Sandbar Restaurant and a short boat trip to Looe Key reef for diving and snorkelling, with discounted boat rentals available through RENTTHEBOATNOW.COM.
2 Bedroom Turquoise Cabin - Big Pine Key, FL
9.1 37 reviews

2 Bedroom Turquoise Cabin

cabin, Big Pine Key
This charming cabin is situated on Big Pine Key, just a short distance from the island's beautiful beaches and natural attractions, offering a tranquil escape. The cabin consistently receives excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom cabin comfortably accommodates up to seven guests, providing a spacious and inviting space for families or groups of friends. The cabin features a well-equipped kitchen, air conditioning, a swimming pool, and a garden, ensuring a comfortable and enjoyable stay. Guests can also enjoy nearby activities such as fishing, kayaking, and snorkeling, as well as dining options in the area.
2 Bedroom Aqua Lodge # 15 Porgie - Big Pine Key, FL
10 9 reviews

2 Bedroom Aqua Lodge # 15 Porgie

boat, Big Pine Key
This Big Pine Key houseboat, situated at the Old Wooden Bridge Resort and Marina, offers convenient access to resort amenities and is a short distance from Big Pine Key's natural attractions.
The self-catering vessel sleeps six guests in one bedroom and one bathroom, boasting a kitchen, air conditioning, and internet access; on-site parking and swimming pool are also available.
Ocean Mist - Big Pine Key, FL
9.3 3 reviews

Ocean Mist

apartment, Big Pine Key
This two-bedroom, two-bathroom house offers tranquil Key Deer Refuge accommodation in Big Pine Key, Florida, conveniently located near Bahia Honda State Park and other attractions.
The property boasts a spacious layout sleeping up to six guests, featuring a fully equipped kitchen with dishwasher, air conditioning, a private garden with outdoor furniture and Traeger grill, plus optional RV parking.
©2026 cozycozy.com