Holiday Rentals in Big Pine Key, FL

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Big Pine Key, FL holiday rentals
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478 Holiday rentals and Airbnb in Big Pine Key, FL

Best family friendly Big Pine Key, FL holiday rentals

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

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.
Charming 3-bedroom House In  Big Pine Key Near Beach And Key West - Big Pine Key, FL
8.4 15 reviews

Charming 3-bedroom House In Big Pine Key Near Beach And Key West

apartment, Big Pine Key
This holiday flat in the Sands district of Big Pine Key is a short walk from the Key West Visitors Centre and Coupon Bight Aquatic Preserve, offering convenient access to local attractions.
Accommodating up to 11 guests across 3 bedrooms and 2 bathrooms, this property boasts a fully equipped kitchen with a lobster pot, complimentary Wi-Fi, and an on-site car park, with the Beaches of the Keys and Blue Hole within easy reach.
Private Florida Keys Escape W/ Pool, Dock, Tiki Bar  Pet Friendly - Big Pine Key, FL
10 1 review

Private Florida Keys Escape W/ Pool, Dock, Tiki Bar Pet Friendly

apartment, Big Pine Key
This spacious four-bedroom, three-bathroom apartment is situated in Summerland Key, Florida, approximately 1.6km from Bahia Honda State Park and offering easy access to Big Munson Island and Blue Hole.
The 110 square metre property boasts a private pool, tiki bar, 25-foot dock with deep-water access, over 61 square metres of outdoor living space, and kayaks and bicycles for guest use; accommodating up to eight guests and including a fully equipped kitchen, laundry facilities, and a large screened-in entertainment area.
Hibiscus House - Heated Pool - Big Pine Key, FL
No reviews

Hibiscus House - Heated Pool

apartment, Big Pine Key
This Big Pine Key holiday home is situated near the National Key Deer Refuge, approximately 24 kilometres from Bahia Honda State Park and 48 kilometres from Key West or Marathon.
Sleeping up to ten guests, this newly renovated four-bedroom property boasts a heated saltwater swimming pool with a tiki hut, three parking spaces plus boat trailer parking near a boat ramp, and two porches offering views of the refuge.

Best Big Pine Key, FL holiday rentals with a pool

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

Vacation Home In Little Torch - Big Pine Key, FL
10 1 review

Vacation Home In Little Torch

apartment, Big Pine Key
This waterside residence in Big Pine Key's Apretreats canal area offers a substantial 61-metre private dockage, including 30 metres on the basin side with a 5.5-metre depth, ideal for large boats.
This five-bedroom, four-bathroom holiday home accommodates up to fourteen guests, featuring two separate 1/1 private downstairs units, a newly finished swimming pool ready by late May, and is strictly pet-free.
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.
Little Torch Treasure: Pool, Dock, Tiki Bar - Big Pine Key, FL
10 3 reviews

Little Torch Treasure: Pool, Dock, Tiki Bar

apartment, Big Pine Key
This four-bedroom, three-bathroom holiday home is situated in Little Torch Key, Lower Florida Keys, a short drive from Big Pine Key and within easy reach of restaurants such as Kiki's Sandbar and the Square Grouper.
Offering a private pool, 25-foot private dock with Gulf of Mexico and Atlantic Ocean access, kayaks, bicycles, and space for up to eight guests, this property also boasts a fully fenced yard, screened entertainment areas, and a propane grill.
Big Pine Turtle House Retreat Short Drive Key-west - Big Pine Key, FL
8.0 2 reviews

Big Pine Turtle House Retreat Short Drive Key-west

apartment, Big Pine Key
Big Pine Turtle House offers a canal-side three-bedroom property, less than 48 kilometres from Key West, providing easy access to water activities and the island's attractions.
This fully renovated house sleeps eight guests, boasting a fully equipped kitchen with modern appliances, three bathrooms, a canal deck with BBQ, beach gear, and an in-house washer and dryer; all within easy reach of the ocean.

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Best Big Pine Key, FL holiday rentals with a balcony

House ∙ 3 Bedrooms ∙ 8 Guests - Big Pine Key, FL
No reviews

House ∙ 3 Bedrooms ∙ 8 Guests

house, Big Pine Key
Maracaibo Manor is a detached house located in Jolly Roger Estates on Little Torch Key, offering deep water canal access and situated approximately 5 kilometres from the renowned Looe Key Reef, ideal for diving, fishing, and snorkelling.
This residence accommodates up to 8 guests with 3 bedrooms and 2 bathrooms, featuring a screened lanai overlooking a tikihut and pool, alongside a separate downstairs apartment with a kitchenette and a private heated and chilled pool, with parking available and the potential for boat lift use.
Castaway On The Keys: Experience Spectacular Open Water Living On Bogie Channel, Pool & Dockage! - Big Pine Key, FL
10 9 reviews

Castaway On The Keys: Experience Spectacular Open Water Living On Bogie Channel, Pool & Dockage!

apartment, Big Pine Key
This luxurious four-bedroom apartment, situated in the Doctor's Arm subdivision of Big Pine Key, offers direct water views of Bogie Channel and is conveniently located near the No Name Pub, 40km from Marathon and 72km from Key West.
The 268 square metre property boasts a private saltwater pool, 80' private dock, a fully equipped kitchen, and sleeps up to ten guests, with pet-friendly options available (up to two dogs under 23kg, fees apply); enjoy fishing and explore the backcountry via the property's private dock.
3-bedroom Waterfront. Cable-wifi, Ac, Hot Tub, Dock. Book For Winter 2026-27 !! - Big Pine Key, FL
10 1 review

3-bedroom Waterfront. Cable-wifi, Ac, Hot Tub, Dock. Book For Winter 2026-27 !!

apartment, Big Pine Key
This three-bedroom Big Pine Key waterfront property, located in Doctor's Arm, offers direct canal access ideal for kayaking and boating, and is within walking/cycling distance of the No Name Pub and a short drive (approximately 8km) from Bahia Honda State Park.
The self-catering apartment sleeps six, boasts a fully equipped kitchen with granite countertops and wine fridge, two bathrooms, a jacuzzi, screened porches, and includes beach chairs, an umbrella, cooler, and bicycles for guest use.
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

Falcons Cove In Big Pine Key - Big Pine Key, FL
10 1 review

Falcons Cove In Big Pine Key

apartment, Big Pine Key
Falcon's Cove, a Big Pine Key half-duplex, offers a canal-front location with a 75-foot private dock, situated approximately 48 kilometres from Key West.
This two-bedroom, 1.5-bathroom property sleeps four, boasting a fully equipped kitchen, air conditioning, parking, internet access, and proximity to local amenities.
Beautiful Keys Home W/ Open Water Views & 90' Dock - Big Pine Key, FL
10 12 reviews

Beautiful Keys Home W/ Open Water Views & 90' Dock

house, Big Pine Key
This Big Pine Key holiday home boasts direct canal access with a private 27-metre dock, situated approximately 21 kilometres from Bahia Honda State Park.
Sleeping eight guests, the three-bedroom, two-bathroom property features a fully equipped kitchen, multiple entertainment areas including a screened porch and Tiki bar, plus kayaks, bikes, and other recreational equipment for water sports enthusiasts.
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.
Barnacle Resort House - Big Pine Key, FL
8.2 10 reviews

Barnacle Resort House

apartment, Big Pine Key
This five-bedroom, six-bathroom property at Barnacle Resort in Big Pine Key, Florida, offers stunning ocean views and is conveniently located near nature trails.
The 16-guest capacity dwelling boasts a fully equipped kitchen, air conditioning, parking, internet access, and kayak/bike rentals, perfect for exploring the island and spotting Key deer.
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