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Holiday rentals in Big Pine Key

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Top-rated holiday rentals in Big Pine Key

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
A coastal scene showcases palm trees swaying gently by the water. Thatched roofs provide shaded seating areas along the shoreline. Sailboats are visible on the horizon, amidst clear turquoise waters under a bright blue sky, with a few fluffy clouds drifting by.
Tiny home in Big Pine Key
4.87 out of 5 average rating, 109 reviews

Cottage 30 min from Key West, free parking, pool

Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

Superhost
Home in Big Pine Key
4.9 out of 5 average rating, 10 reviews

Keys Beach Retreat Close to Key West

Your family will be close to everything when you stay at this centrally-located place. we are only 3 miles from Bahia Honda Beach and about 27 Miles from Key West. We are perfect for nature lovers and adventure seekers. 1. National Key Deer Refuge: Home to the endangered Key deer, this refuge offers beautiful trails and great for wildlife viewing and 2.Looe Key Reef: A popular snorkeling and diving location, featuring vibrant coral reefs. 3.Sand bars nearby & world famous fishing spots.

Top guest favourite
Home in Cudjoe Key
5 out of 5 average rating, 32 reviews

Oceanfront Cottage with 60’ Dock

Oceanviev Serenity provides stunning open water views, and a 60 foot seawall for your boat. Comes with paddle board, kayaks, and more. Newly renovated 2BR cottage sleeps MAXIMUM OF FOUR (4) GUESTS, with a King in the Master BR and one Queen size bed Guest BR (both with new JW Marriott mattresses for comfort). All new appliances! Enjoy resort amenities like a pool, hot tub, tennis, and marina store. Just 30 minutes from Key West. $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON).

Guest favourite
Home in Cudjoe Key
4.95 out of 5 average rating, 82 reviews

Ocean~View w/ Dock, Pool, Kayaks, King Bed

Experience waterfront luxury in Venture Out on peaceful Cudjoe Key! Enjoy stunning Atlantic Ocean views, amazing sunsets, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Keep your boat at the house and reach the Atlantic or Gulf in minutes. Near Key West, this updated Keys getaway includes resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, especially lobster season in August, so book now!

Guest favourite
An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.
Apartment in Summerland Key
4.96 out of 5 average rating, 27 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Superhost
A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.
Cottage in Little Torch Key
4.88 out of 5 average rating, 179 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Superhost
The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.
Home in Upper Sugarloaf Key
4.93 out of 5 average rating, 120 reviews

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

Top guest favourite
A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.
Houseboat in Marathon
4.95 out of 5 average rating, 64 reviews

b watervibe

Disfruta de los sonidos de la naturaleza cuando te quedes en este lugar único. Es algo diferente para disfrutar con tu pareja de un momento romántico y divertido y así relajarse y olvidarse de la vida cotidiana. Puedes disfrutar de la pesca ,de paseos en kayak ,vivir una aventura y disfrutar de otras actividades locales.Prueba de la expericiensa y ya ustedes diran.Esta casa flotante ofrece un espacio para 2 adultos. Está Esta es una experiencia de Acampada .

Superhost
A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.
Home in Cudjoe Key
4.88 out of 5 average rating, 130 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Superhost
A spacious RV is positioned on a gravel lot, surrounded by lush greenery. Tall palms provide shade, while a decorative potted plant adds a touch of color. The exterior features large windows and a sleek design, offering a welcoming exterior view.
Camper van/Motorhome in Big Pine Key
4.85 out of 5 average rating, 13 reviews

Glamping in the Keys

This roomy RV is set in the heart of the Key Deer Refuge and contains everything you need for a relaxing vacation. The friendly neighborhood contains a community pool, coin laundry and club house. You'll be in a well known fishing area with several restaurants, nature parks, including Bahia Honda State Park and a grocery store. Key West is 30 miles west and Marathon is 20 miles east across the picturesque 7-Mile Bridge.

Superhost
Tiny home in Big Pine Key
4.93 out of 5 average rating, 102 reviews

Tiny Fish Haus

Great location in the lower keys , 28 miles to Key West..8 miles to Bahia Honda State Park and right next to the National Key Deer Refuge! Relax on our covered patio next to a large Swimming Pool, Cook dinner on a Blackstone grill and enjoy WIFI, Games, a Flat Screen TV , we have Premium Organic Bedding on our Queen beds for comfort. Turkish Towels for bath and beach..Explore Big Pine Key with our 2 beach cruiser bicycles!

Guest favourite
Tiny home in Summerland Key
4.97 out of 5 average rating, 37 reviews

Cottage

Experience island living at Sugarloaf RV Resort's NEW Cottages in the Lower Keys, just 25 minutes from Key West. These Two-Bedroom Cottages sleep up to 4 guests with 2 Queen beds. Features include a kitchenette with double burner stovetop, dorm fridge, microwave, single serve coffee maker, toaster, plus outdoor seating. Coastal charm with keys-style design and a private patio perfect for morning coffee or sunset relaxation.

Popular amenities for Big Pine Key holiday rentals

When is the best time to visit Big Pine Key?

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Frequently Asked Questions

  • What are the best places to stay in Big Pine Key?

    Big Pine Key has inviting stays near waterfronts, serene neighborhoods, and areas surrounded by lush nature. Those seeking quiet relaxation or easy access to outdoor activities often choose homes close to mangroves or community parks.

  • What are the best things to do in Big Pine Key with kids?

    Explore nature trails, picnic around local parks, or visit nearby beaches where families often enjoy swimming and snorkeling. Kids frequently delight in dolphin encounters or learning about local wildlife at nature centers.

  • What are some of the best things to do in Big Pine Key?

    Big Pine Key has nature walks, kayaking in calm waters, and snorkeling around reef areas. Visitors frequently explore the National Key Deer Refuge or unwind with fishing and wildlife watching.

  • How is the weather in Big Pine Key?

    Big Pine Key has warm, humid weather most of the year, ranging from around 65–91°F (19–33°C). Summers bring higher rainfall, while winter months are drier and comfortable for outdoor activities.

  • When is the best time to visit Big Pine Key?

    Late fall through early spring is often recommended for milder temperatures and reduced rainfall. Outdoor activities such as hiking, boating, and wildlife viewing become especially popular during these months.

  • What are the best places to visit in Big Pine Key?

    Visitors are often drawn to the National Key Deer Refuge, local beaches, and nearby nature preserves. Those interested in unique ecosystems can explore mangrove areas or designated wildlife observation spots.

  • What are some hiking trails in Big Pine Key?

    Big Pine Key has nature trails within wildlife refuges and community parks, where hikers explore pine forests and mangrove paths. The area around the National Key Deer Refuge is frequently suggested for easy walks and wildlife sightings.

  • What are some family activities we can do in Big Pine Key?

    Families often visit local beaches for swimming and shell collecting, participate in kayaking, or explore interactive exhibits at nature centers. Picnics in shaded parks and spotting Key deer are popular ways to connect with the area’s natural surroundings.

  • What are some of the best day trip ideas from Big Pine Key?

    Consider exploring neighboring islands, historic sites, or additional nature reserves for snorkeling, boating, or cultural activities. Art galleries, marine discovery centers, and local eateries in nearby communities are frequently suggested for a change of pace.

  • Are there any pet friendly accommodations available in Big Pine Key?

    Many accommodations in Big Pine Key welcome pets, especially in neighborhoods near parks and waterfronts. Outdoor spaces such as community trails and dog-friendly beaches make it easy to enjoy time with your companion.

  • What are some local tips for visiting Big Pine Key?

    Bring insect repellent, as local nature areas can have mosquitoes, and consider reusable water bottles to stay hydrated. Early mornings are often the best time for wildlife spotting, and respect preservation areas for Key deer and other fauna.

  • What is Big Pine Key known for?

    Big Pine Key is known for its protected Key deer population, expansive tropical forests, and laid-back atmosphere. The National Key Deer Refuge, snorkeling sites, and kayaking routes highlight its connection to unique coastal ecosystems.

  • What are the best hidden gems to explore in Big Pine Key?

    Explore secluded mangrove paths, lesser-known beaches, and local artisan shops for a quieter glimpse of Big Pine Key. Some tide pools around nature preserves are frequently suggested for their tranquil beauty and interesting marine life.

  • What are the best foods to try in Big Pine Key?

    Fresh seafood such as snapper, grouper, and stone crab are frequently suggested, along with locally inspired dishes like conch fritters. Tropical fruits and key lime pie showcase regional flavors many travelers enjoy.

  • What should I bring for a trip to Big Pine Key?

    Pack lightweight clothing, sun protection, insect repellent, and a reusable water bottle. For water activities, bring snorkel gear, swimwear, and sandals; binoculars can enhance wildlife viewing experiences.

  • What is the nightlife in Big Pine Key like?

    Big Pine Key has laid-back nightlife with casual bars, live music at local venues, and waterfront gathering spots. Social evenings are often centered around fresh seafood, storytelling, and community events.

  • What are the most popular events or festivals in Big Pine Key?

    Big Pine Key frequently hosts nature-centered events and seasonal wildlife festivals, especially in spring and autumn. Community gatherings, artisan markets, and environmental awareness celebrations are often recommended.

  • Are there family friendly vacation rentals in Big Pine Key?

    Big Pine Key has family friendly vacation rentals with spacious interiors, outdoor areas, and proximity to community parks or beaches. Many hosts provide amenities like cribs, outdoor grills, and recreational equipment to enhance your stay.

Quick stats about holiday rentals in Big Pine Key

  • Total holiday rentals

    Explore 240 holiday rentals in Big Pine Key

  • Nightly prices starting at

    Big Pine Key holiday rentals start at £29 per night before taxes and fees

  • Verified guest reviews

    Over 5,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    180 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 140 rentals that welcome pets

  • Holiday rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    240 of Big Pine Key holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Big Pine Key rentals

  • 4.8 Average rating

    Big Pine Key stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Big Pine Key