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Vacation rentals in Big Pine Key

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Quick stats about vacation rentals in Big Pine Key

  • Total vacation rentals

    Explore 270 vacation rentals in Big Pine Key

  • Nightly prices starting at

    Big Pine Key vacation rentals start at €43 per night before taxes and fees

  • Verified guest reviews

    Over 5,510 verified reviews to help you choose

  • Family-friendly vacation rentals

    190 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Vacation rentals with a pool

    130 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    260 of Big Pine Key vacation rentals include wi-fi 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 vacation rentals in Big Pine Key

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

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Guest favorite
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
4.89 out of 5 average rating, 177 reviews

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!

Top guest favorite
Home in Cudjoe Key
5.0 out of 5 average rating, 48 reviews

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

Guest favorite
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
4.81 out of 5 average rating, 36 reviews

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.

Guest favorite
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
4.88 out of 5 average rating, 131 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
Houseboat in Marathon
4.77 out of 5 average rating, 148 reviews

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.

Superhost
Home in Marathon
5.0 out of 5 average rating, 4 reviews

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

Guest favorite
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
4.96 out of 5 average rating, 210 reviews

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.

Guest favorite
A scenic waterfront area is depicted with vibrant green lounge chairs positioned on a sandy peninsula. Surrounding waters provide a tranquil blue hue. Wooden docks extend into the bay, complemented by lush palm trees and colorful buildings in the background.
Home in Summerland Key
4.95 out of 5 average rating, 116 reviews

Waterfront Anchor House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). 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 point and enjoy the underwater scenery!

Top guest favorite
Lounge chairs with blue umbrellas surround a sandy beach area, providing a relaxed setting by the water. Steps lead down to the shoreline, where vibrant greenery and palm trees offer a natural frame against the bright blue sky and turquoise sea.
Home in Summerland Key
4.95 out of 5 average rating, 20 reviews

Ocean front classic keys cottage

This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breathtaking sunrises and romantic moonrises, seabirds,dolphins, and a nearly south-easterly breeze. This lovely hideaway is next to last home on dead end street, this 3 BRs, 2 baths ground level home has a large kitchen and Master suite. this location is only 30 minutes from the historic key west, close to restaurants and a nearby marina.

Top guest favorite
A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.
Home in Cudjoe Key
4.99 out of 5 average rating, 74 reviews

Waterfront, Dock, Pool, Pickleball, near Key West!

Welcome to “The Barnacle” your waterfront home in the Florida Keys! Dock your boat behind this charming two bedroom home with 35’ sea wall! We have direct access to some of the best fishing, snorkeling and diving in the Keys! Beautiful neighborhood loaded with amenities. Bring a pole and fish from the dock! Relax, enjoy and have a wonderful vacation experience. Visit YouTube “The Barnacle at Venture Out”. Swim, Fish, Dive …Repeat!

Top guest favorite
Home in Marathon
4.94 out of 5 average rating, 205 reviews

70ft Dock, Bikes, Beach, Spacious, VACA23-16

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

Top guest favorite
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
4.93 out of 5 average rating, 96 reviews

b watervibe

Enjoy the sounds of nature when you stay in this unique place. It's something different to enjoy with your partner of a romantic and fun moment and thus relax and forget about the everyday life. You can enjoy fishing, kayaking, adventure, and other local activities. A great camping experience for guests who like something fun and different. Try it and you'll tell me. It offers a space for 2 people.

Popular amenities for Big Pine Key vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

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 vacation rentals in Big Pine Key

Guest favorite
A serene canal view during sunset, showcasing vibrant orange and pink hues reflecting off the water. A concrete dock extends into the water, equipped with a fish cleaning station. A table and chairs are positioned nearby for relaxation and enjoyment of the picturesque scene.
Home in Cudjoe Key
4.89 out of 5 average rating, 18 reviews

Blue Heaven Waterfront Home

Guest favorite
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
4.85 out of 5 average rating, 60 reviews

Relaxing and Inviting home with 35' Private Dock

Top guest favorite
A serene patio area showcases a private pool with illuminated edges, creating a calming ambiance. Outdoor furniture is arranged on a synthetic grass surface, framed by lush greenery and a tranquil water view, as the sky transitions to sunset hues in the background.
Home in Marathon
4.98 out of 5 average rating, 40 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Guest favorite
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
4.88 out of 5 average rating, 42 reviews

Yellow Home - Receive $400 towards a Boat Rental!

Superhost
Home in Cudjoe Key
4.92 out of 5 average rating, 97 reviews

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

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
4.8 out of 5 average rating, 15 reviews

Oceanview Rooftop Retreat 3BR 3BA in Marathon FL

A 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
4.8 out of 5 average rating, 286 reviews

New Waterfront 2/1 Cabin With Loft at Bonefish Bay

Guest favorite
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
5.0 out of 5 average rating, 19 reviews

The Tarpon Retreat

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.

Destinations to explore