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Holiday rentals in Big Pine Key

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Quick stats about holiday rentals in Big Pine Key

  • Total holiday rentals

    Explore 270 holiday rentals in Big Pine Key

  • Nightly prices starting at

    Big Pine Key holiday rentals start at ₹4,756 per night before taxes and fees

  • Verified guest reviews

    Over 5,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    190 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    130 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    260 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!

Top-rated holiday rentals in Big Pine Key

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

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Guest favourite
An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.
Cottage in Cudjoe Key

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

4.89 out of 5 average rating, 177 reviews
Guest favourite
A tranquil pool is set against a backdrop of palm trees and a vibrant sunset. The water reflects the hues of the sky, creating a calming scene. Loungers are positioned along the poolside, offering a inviting space to relax.
Cottage in Cudjoe Key

2Bd/1Ba Waterfront Retreat w/35’ Dock

Discover the FL Keys in this bright & beachy 2-queen bed, 1-bath waterfront modular home in Venture Out on Cudjoe Key. Enjoy your fresh catch in the full kitchen, laundry in-house, nice wide canal with 35’ dock for your boat just steps from your door. Indulge in unparalleled amenities & scenic beauty: oceanfront pool, hot tub, marina w/marine fuel, wash station, store; tennis, bball, pickle ball, & playground. $125 add’l resort fee paid direct to Venture Out at gate. Incl Bikes & kayaks for use.

4.83 out of 5 average rating, 35 reviews
Top guest favourite
Home in Cudjoe Key

Oceanfront Cottage with Open Water Views

Oceanview 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. One-time $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON

5.0 out of 5 average rating, 47 reviews
Guest favourite
A serene beach scene captures soft sands meeting clear waters under a bright blue sky. Lush palm trees frame the view, while visitors are seen enjoying the tranquil coastline and gentle waves. Green foliage and distant beach cabanas are also visible, enhancing the natural beauty.
Tiny home in Big Pine Key

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!

4.88 out of 5 average rating, 131 reviews
Superhost
Tiny home in Summerland Key

Cottage

Experience island living at Sugarloaf RV Resort & Cottages in the Lower Keys, just 25 minutes from Key West. Our NEW Two-Bedroom Cottages sleep up to 6 guests with two queen beds and a full-size pull-out sofa. Enjoy a kitchenette with a double-burner stovetop, pots, pans, dorm fridge, microwave, K-Cup coffee maker, toaster, dishes, and utensils. Relax on your private patio and enjoy resort amenities including a heated / chilled pool, kayaks, paddle boards, bicycles, and a peaceful private lake.

4.94 out of 5 average rating, 80 reviews
Superhost
Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.

4.77 out of 5 average rating, 148 reviews
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

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!

4.89 out of 5 average rating, 184 reviews
Superhost
Home in Marathon

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

5.0 out of 5 average rating, 4 reviews
Guest favourite
A scenic view of a calm waterway, featuring a thatched-roof hut on a dock and several palm trees. A second dock with covered areas can be seen in the distance under clear blue skies, creating a relaxing waterfront setting.
Home in Cudjoe Key

Relaxing and Inviting home with 35' Private Dock

This 2 bedroom, one bath located in Venture Out on Cudjoe Key, FL. Featuring 35' of dock space. 23 miles outside of Key West!. Venture Out is a gated community that features a community pool, hot tub, tennis courts, basketball coart, boat ramp and much more. There is a dishwasher, grill, TV & free WIFI. Unit includes a 2 person Kayak an 1 Paddle board at no extra charge. ATTENTION: The community charges a non-refundable security/registration fee upon arrival to the renter.

4.85 out of 5 average rating, 60 reviews
Superhost
Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.
Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

4.86 out of 5 average rating, 609 reviews
Guest favourite
An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.
Home in Cudjoe Key

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

4.96 out of 5 average rating, 209 reviews
Guest favourite
A spacious outdoor dining area features a glass-top table with several red chairs, set against a vibrant backdrop of greenery and water. The view of the calm sea and fluffy clouds can be seen in the distance, enhancing the tranquil setting.
Home in Cudjoe Key

Yellow Home - Receive $400 towards a Boat Rental!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our homes staying between the dates of Sept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026 Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home. Kayaks included. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

4.88 out of 5 average rating, 42 reviews

Popular amenities for Big Pine Key holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Big Pine Key's top sights

No Name Key

3 locals recommend

Big Pine Key Flea Market

13 locals recommend

Big Pine Bicycle Center

12 locals recommend

Other great holiday rentals in Big Pine Key

Guest favourite
Flat in Key West

Designer Waterfront Estate - Lunara Bay Collection

4.85 out of 5 average rating, 33 reviews
Superhost
A resort-style pool is surrounded by lounge chairs, set on a brick patio with a view of palm trees and the ocean. The scene is bright and open, showing a clear sky with scattered clouds, enhancing the outdoor leisure space.
Home in Marathon

Oceanview Rooftop Retreat 3BR 3BA in Marathon FL

4.8 out of 5 average rating, 15 reviews
Superhost
Home in Cudjoe Key

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks

4.92 out of 5 average rating, 97 reviewsThe kitchen features modern white cabinetry with a granite countertop. Appliances include a refrigerator, oven, microwave, and dishwasher. A coffee maker is also visible, along with a sink located beneath a window with patterned curtains. The backsplash is designed with light-colored tiles for an elegant touch.
Flat in Big Pine Key

New Deluxe Duplex Unit, 2 Queen Beds, Unit G-4

4.81 out of 5 average rating, 104 reviewsA rustic wooden cabin features a welcoming entrance with a sturdy set of steps leading to the front door. Large windows allow natural light to illuminate the exterior, which is complemented by a natural stone pathway and lush greenery in the background.
Cabin in Marathon

New Waterfront 2/1 Cabin With Loft at Bonefish Bay

4.8 out of 5 average rating, 286 reviews
Guest favourite
An aerial view captures a charming home situated beside a tranquil canal, bordered by lush greenery and tropical landscapes. The house features a light blue exterior with a white roof. The 60-foot dock extends into the water, providing convenient access for boating and water activities.
Home in Big Pine Key

The Tarpon Retreat

5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Big Pine Key

Cozy house with relaxing pool

4.83 out of 5 average rating, 12 reviews
Home in Big Pine Key

Keys Beach Retreat Close to Key West

4.77 out of 5 average rating, 22 reviews

When is the best time to visit Big Pine Key?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price₹23,778₹23,968₹24,444₹23,588₹20,830₹21,400₹20,925₹19,023₹18,262₹19,688₹20,164₹20,069
Avg. temp21°C22°C24°C25°C27°C29°C30°C30°C29°C27°C25°C23°C

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.

Destinations to explore