Holiday rentals in Big Pine Key
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Top-rated holiday rentals in Big Pine Key
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Oceanfront Rooftop Views w/ 75ft of Dockage
Welcome aboard Captains Rooftop, Your 4BR Rooftop Deck Hot Tub Oasis on a direct ocean access canal with 75ft of dockage. This three story stilted rooftop home provides a unique unforgettable Florida Keys experience for your entire family. 🏊♂️ 2 Luxury jet Hot Tubs (One on the roof, one in the backyard) ⛵ Private 75ft dock surrounded by a mangrove jungle 🕹️ Foosball Table 🍳 Rooftop patio with BBQ grill & open ocean view dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable
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
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!
Perfect Couple Oasis!
You’ll treasure your time at this memorable location. New camper recently added to lot. Queen bedroom, bathroom, open living room with a full kitchen. Located on Big Pine Key, FL, between Marathon and Key West. Parking for 1 vehicle on lot, large vehicles will not fit. Key deer and roosters walk around park. Community pool and laundry facility. Great place to relax after fun in the sun or a night on the town! Renters must 25 years old or over. Community requires a rental form to be completed.
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.
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!
Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***
Gorgeous Ocean View Home!
Beautiful family friendly ocean view home centrally located in the heart of Marathon (only 10min from Sombrero Beach) were you’ll be able to do many things like snorkeling, fishing, boating, Scuba, museums, visit the aquarium, and/or the dolphin research center, and even dine on the water with many restaurants selections near by. This property does NOT have dock space for a boat or trailer parking. Licensed and inspected by the city of Marathon Lic.# VACA-23-144
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 .
3 Bedroom Home - Perfect Location & Private Pool
The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street and all major attractions. This rental listing includes the second and third floors of the home, which features three bedrooms, a private swimming pool, spacious living areas inside and outside, off-street parking, and a newly renovated chef's kitchen to prepare meals. The first story of the home will be left vacant when this listing is rented.
Palm Breezes! Room for Everyone on the Ocean.
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.
*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.
Popular amenities for Big Pine Key holiday rentals
Other great holiday rentals in Big Pine Key
Kelly’s Kabin - Private FL Keys Cottage
Cudjoe Key Home with a View
106- Newly Renovated House with Oceanview and Pool
Starlight Serenity - Hideaway with Stunning Views
Island Girl Big Pine Key
The Island Gypsy
Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean
Cozy house with relaxing pool
When is the best time to visit Big Pine Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £186 | £188 | £192 | £152 | £146 | £153 | £164 | £149 | £143 | £154 | £158 | £157 |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°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 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 £30 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!
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- Sombrero Beach
- Smathers Beach
- Ernest Hemingway Home & Museum
- Robbies Marina Of Islamorada
- Seven Mile Bridge
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Conch Key
- Dolphin Research Center
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- History Of Diving Museum
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Curry Hammock State Park
- Key West Aquarium