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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, 159 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.

Top guest favorite
A serene view overlooks the water at sunrise, with soft pastels reflecting on the surface. A white patio table and chairs are positioned under the covered porch, inviting relaxation. The horizon features gentle clouds and distant islands, creating a peaceful atmosphere.
Home in Cudjoe Key
4.89 out of 5 average rating, 57 reviews

Rise And Shine On The Water

Spectacular sunrise view! Room to park one vehicle & have a free overflow lot if needed. Community amenities include tennis, pickle ball, bocce ball, heated pool, hot tub, designated swim area, pool table, ping pong, & darts. We provide bedding, towels, pots & pans., GRILL, TV in living room & one bedroom. We will also have boat bumpers installed all along the concrete dock that will accommodate a 40' boat. We offer 100% money back if your rental is in the projection cone of a named hurricane.

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, 104 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
4.89 out of 5 average rating, 94 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 sandy outdoor area features a fire pit surrounded by several colorful adirondack chairs. A large Tiki hut provides shade, with high-top bar seating nearby. The serene water view reflects soft evening light, enhancing the inviting space.
Home in Big Pine Key
4.85 out of 5 average rating, 26 reviews

Oceanfront new 360’ dock, tiki hut-dogs OK

Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut, fire pit area, and beach with NEW 360' dock for any size boat and fishing!! You will not want to go inside, but when you do, you will find a very "Keysey" living space with plenty of water views. Only 9 miles from Bahia Honda State Park one of top 25 beaches in the US. We are also famous for key deer only found on Big Pine Key. They are friendly and everywhere. You can also walk to No Name Pub a famous eatery.

Guest favorite
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.
Condo in Summerland Key
5 out of 5 average rating, 18 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
4.89 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
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
4.89 out of 5 average rating, 507 reviews

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!

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, 46 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

Guest favorite
Tiny home in Big Pine Key
4.93 out of 5 average rating, 98 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!

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

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor

Captain's Cove, your 4BR waterfront escape in Marathon, set on a quiet canal with direct ocean access. Designed for unforgettable Keys living for families and boaters alike. 🏊‍♂️ Private backyard pool ⛵ 30’ boat dock + 4 kayaks 🍳 Covered outdoor kitchen & BBQ 🚿 Spa-style rain & jet showers w/ luxury toiletries 🛏️ Ground-level comfort for 8 🐾 Pet & kid friendly

Top guest favorite
Adirondack chairs are positioned on a coastal patio, providing views of the water and distant shoreline. Gentle waves reflect the sky, dotted with clouds. A palm tree sways lightly nearby, enhancing the serene environment by the water's edge.
Home in Cudjoe Key
4.96 out of 5 average rating, 67 reviews

Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW

Don’t be fooled by canal front listings. Ocean's Edge has forever ocean views, a 52 foot seawall, paddle boards, bikes, a kayak, 24 hour security and is just 30 minutes from Duval Street in Key West.

Popular amenities for Big Pine Key vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Other great vacation rentals in Big Pine Key

Guest favorite
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/RV in Big Pine Key
4.92 out of 5 average rating, 12 reviews

Glamping in the Keys

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, 186 reviews

Cudjoe Key Home with a View

Guest favorite
A bright, elevated house with a coastal design sits amid lush palm trees under a clear blue sky. Vibrant green shutters contrast with the white exterior, while a spacious deck and railing are visible, inviting outdoor relaxation. The surrounding landscape features well-maintained shrubbery.
Home in Cudjoe Key
5 out of 5 average rating, 17 reviews

The Lookout #659 Venture Out - Gated Community

Superhost
An open-concept interior features a full kitchen with modern appliances and ample cabinetry. A comfortable seating area is present, with a grey sofa and decorative yellow pillow. Natural light floods through the windows, highlighting the wooden beams and white walls that create a bright and welcoming space.
Houseboat in Marathon
4.74 out of 5 average rating, 84 reviews

Tiny Home Aqua Lodges 2/1

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

Starlight Serenity - Hideaway with Stunning Views

Top guest favorite
Home in Cudjoe Key
5 out of 5 average rating, 23 reviews

Oceanfront Cottage with 60’ Dock

Top guest favorite
A spacious backyard features a heated swimming pool surrounded by colorful tropical landscaping. Sun loungers line the poolside, with palm trees offering shade. A hammock is visible in the background, and a canal can be seen just beyond the pool area.
Home in Marathon
5 out of 5 average rating, 24 reviews

Keys Waterfront Pool Home - Dock - Ocean - Kayaks

Top guest favorite
An outdoor theater area is outlined by a modular seating arrangement with blue cushions and dark wicker. A large projection screen is mounted on a wooden wall, creating an inviting space for movie nights. Soft lighting from overhead strands completes the ambiance.
Home in Marathon
4.92 out of 5 average rating, 39 reviews

Oceanview Marathon - Screened Porch, Theater & Bar

When is the best time to visit Big Pine Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR3,725 ZARR3,895 ZARR3,861 ZARR3,455 ZARR3,319 ZARR3,471 ZARR3,725 ZARR3,387 ZARR3,251 ZARR3,505 ZARR3,590 ZARR3,573 ZAR
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.

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 R1,016 ZAR 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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