Holiday houses in Big Pine Key
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Top-rated holiday rentals in Big Pine Key
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Blue House - 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. Vacation home has a view over Cudjoe Bay to the Atlantic from the common deck and from the private pool deck. 4 bedroom and 2 bathrooms. Large dock with water access for a small boat.
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.
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.
Tiny House | 35 min to KW + Free Parking & Pool
Discover a hidden gem in the Florida Keys with this charming Tiny House, surrounded by nature and the famous Key Deer. Located in the peaceful Breezy Pine RV Resort, it offers a cozy yet spacious layout for the whole family. Relax outdoors on the private patio with sofa and grill, perfect for enjoying the laid-back Keys lifestyle. With all the essentials for comfort and just a short drive to Key West, Bahia Honda beaches, shops and restaurants. This retreat is ideal for relaxation and fun.
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.
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!
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
Waterfront Haven 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 Anchor 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!
Coco Plum Waterfront Hideaway Home in Marathon
This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.
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!
Waterfront Oceanside, 60 Ft Dock, As seen on HGTV
See our home on HGTV's "Vacation House for Free", (Rental Lisc#VACA-20-690) BRING YOUR BOAT TO OUR PRIVATE 60 FOOT DOCK WITH 30 AMP SHORE POWER OUTLET. We call our home "Bahama Breeze" because that's what you feel blowing in as you spend your vacation at this Oceanside single family home.
Popular amenities for Big Pine Key holiday rentals
Other great holiday rentals in Big Pine Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Starlight Serenity - Hideaway with Stunning Views
Oceanview Rooftop Retreat 3BR 3BA in Marathon FL
OCEANIA... water front cottage retreat ~
Nautical Retreat
Keys Beach Retreat Close to Key West
Casa Marquez
The Hideaway - Private Paradise at its Best!
When is the best time to visit Big Pine Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $376 NZD | $393 NZD | $390 NZD | $349 NZD | $335 NZD | $350 NZD | $376 NZD | $342 NZD | $328 NZD | $354 NZD | $362 NZD | $360 NZD |
| 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 250 holiday rentals in Big Pine Key
Nightly prices starting at
Big Pine Key holiday rentals start at $103 NZD per night before taxes and fees
Verified guest reviews
Over 4,920 verified reviews to help you choose
Family-friendly holiday rentals
190 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 140 rentals that welcome pets
Holiday 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 holiday 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!
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- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- Sea Oats Beach
- Long Beach
- Bahia Honda State Park
- Conch Key
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Sunset Park
- Dolphin Research Center
- Robbies Marina Of Islamorada
- Key West Butterfly & Nature Conservatory
- Florida Keys Aquarium Encounters
- Key West Lighthouse Museum
- The Turtle Hospital
- History Of Diving Museum
- Southernmost Point
- Boyd's Key West Campground