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Vacation rentals in Big Pine Key

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Top-rated vacation rentals in Big Pine Key

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

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Top guest favorite
A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.
Cottage in Cudjoe Key
4.94 out of 5 average rating, 157 reviews

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Guest favorite
The living room features a light-colored couch and love seat, complemented by decorative pillows. A coffee table sits in the center, and a Smart TV is mounted on the wall. Natural light is provided by the sliding glass doors, leading to an outdoor space.
Cottage in Cudjoe Key
4.96 out of 5 average rating, 103 reviews

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Guest favorite
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
4.9 out of 5 average rating, 90 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!

Guest favorite
A spacious deck is visible, offering a view of the Gulf of Mexico and a nearby dock. Comfortable outdoor seating is arranged against the backdrop of lush greenery and a sandy shoreline, providing a relaxing setting to enjoy the scenery.
Home in Marathon
4.82 out of 5 average rating, 108 reviews

Beautiful Waterfront book now 2026 filling up fast

This property is like having your own private resort. We are on the Gulf of Mexico with a Million-dollar waterfront view & sunsets. 4BR + bonus room w/queen bed & futon. 2 full bathrooms 4 TVs. Pool, Private Dock. Watch the Dolphins daily. We a located next to the World-Famous Dolphin Research Center. House has wrapped around deck plenty of seating inside/out. Large private yard with plenty of room for all your needs. Walking distance to restaurant, marina. Kayaks/Paddleboards mostly available.

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.
Home in Cudjoe Key
4.78 out of 5 average rating, 23 reviews

2Bd/1Ba Waterfront Retreat w/35’ Dock

Discover the FL Keys in this bright & beachy 2-queen bed, 1-bath waterfront 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 your use.

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
4.92 out of 5 average rating, 12 reviews

Blue Heaven Waterfront Home

Lobstering paradise 2 houses from open water, deep 60' canal, gorgeous water views, direct access to the Atlantic/Gulf, 35' dock/seawall. 3 zone mini split A/C and heat, overhead ceiling fans, fully stocked kitchen, microwave, washer/dryer, 42" Smart TV in living room and master bedroom, WIFI. King size bed in the master, queen bed in 2nd bedroom, and a queen sofa in the living room. Beach towels, linens. Marina store with bait & fuel onsite, 2 wide boat ramps, pool, hot tub & Rec center.

Superhost
Home in Cudjoe Key
4.83 out of 5 average rating, 6 reviews

Tropical Paradise

Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.

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
4.89 out of 5 average rating, 177 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
Bungalow in Cudjoe Key
4.8 out of 5 average rating, 25 reviews

Oceanfront Bungalow Venture Out

Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. 52' concrete dock/seawall complete with dock posts and fishing table. Lovely decor. Bocce ball, playground. Tennis, Hot Tub, 2 pools. Recreation center with billiards, darts, and ping pong. Post Office and a Library 24 Hour Gated Security. . 40" screened TV. WIFI Saturday to Saturday only 7 night minimum.

Top guest favorite
Home in Marathon
4.94 out of 5 average rating, 197 reviews

Spacious 3Br/3Ba, 70ft Dock, March avail 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.

Guest favorite
A boat is docked at a private marina, showcasing a spacious outdoor area. A fish cleaning station is visible nearby, along with a hose and power source. Colorful buildings line the waterfront, and clear blue skies reflect over the water.
Home in Cudjoe Key
5 out of 5 average rating, 9 reviews

35’ dock/Completely Remodeled VO 366

Dock your boat and enjoy open water views. Our 2 bedroom 2 bathroom newly remodeled home is perfect for your family get away or a couples retreat. Home comes with 2 kayaks and 2 bikes. The gated community offers pool, beach area, hot tub, pickle ball, playground area, basketball and a recreation room. THERE IS A $125 RESORT FEE DUE AT THE GATE UPON ENTRY.

Guest favorite
A charming waterfront villa is framed by lush palm trees, featuring a spacious sandy area with vibrant landscaping. A boat is docked nearby, with soft clouds drifting across the blue sky, contributing to a serene outdoor environment.
Home in Cudjoe Key
4.93 out of 5 average rating, 14 reviews

Secluded Waterfront home, Views, Dock, Amenities,

Step into your private oasis! This stunning home features a sprawling outdoor space, perfect for boating, fishing or relaxing under the stars. Complete with a beautiful landscaped butterfly garden, park benches and tables. This property is one of a kind compared to space and privacy. Perfect for relaxation and rejuvenation.

Popular amenities for Big Pine Key vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Other great vacation rentals in Big Pine Key

A charming exterior of a coastal home is presented, framed by tall palm trees. The front features a covered porch with steps leading to the entrance. Large windows allow natural light to enter. A spacious driveway is visible, complimented by a gravel landscape.
Home in Cudjoe Key
4.57 out of 5 average rating, 60 reviews

Relaxing Cottage in Cudjoe

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
4.98 out of 5 average rating, 63 reviews

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

Home in Marathon
5 out of 5 average rating, 8 reviews

Little Venice Family Affair 2 bedroom 1 bath One B

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
4.97 out of 5 average rating, 184 reviews

Cudjoe Key Home with a View

Superhost
A spacious pool area is framed by tropical landscaping, showcasing a large, clear swimming pool. Sun loungers are arranged around the pool, providing places to relax. A tiki hut offers shaded seating options, enhancing the outdoor living experience with serene water views.
Home in Marathon
4.8 out of 5 average rating, 40 reviews

Luxury Waterfront Retreat with Dockage & Pool

Guest favorite
Home in Summerland Key
4.91 out of 5 average rating, 11 reviews

Starlight Serenity - Hideaway with Stunning Views

Guest favorite
A beach home with a turquoise roof is nestled among palm trees and tropical landscaping. Two sets of chairs in yellow and blue are positioned on the sandy area in the foreground, inviting relaxation. A private pool and lush greenery are visible in the background.
Home in Marathon
4.92 out of 5 average rating, 72 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Superhost
An empty gravel lot is showcased, surrounded by lush greenery and palm trees. A picnic table is positioned to one side, providing a space for outdoor dining. The open area suggests ample room for a camper and additional parking.
Campsite in Big Pine Key
4.75 out of 5 average rating, 128 reviews

Bring Your Own RV! Our Lot Your RV B6 No Tents

When is the best time to visit Big Pine Key?

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Avg. priceﺩ.ﺇ808ﺩ.ﺇ845ﺩ.ﺇ837ﺩ.ﺇ749ﺩ.ﺇ720ﺩ.ﺇ753ﺩ.ﺇ808ﺩ.ﺇ735ﺩ.ﺇ705ﺩ.ﺇ760ﺩ.ﺇ779ﺩ.ﺇ775
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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 vacation rentals in Big Pine Key

  • Total vacation rentals

    Explore 250 vacation rentals in Big Pine Key

  • Nightly prices starting at

    Big Pine Key vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

  • Verified guest reviews

    Over 4,920 verified reviews to help you choose

  • Family-friendly vacation rentals

    190 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 140 rentals that welcome pets

  • Vacation rentals with a pool

    110 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    240 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!

Destinations to explore

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