Are there vacation rentals with a dedicated workspace in Big Pine Key?

Yes! Work meets play with ease at over 90 vacation rentals in Big Pine Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

Are there pet-friendly vacation rentals in Big Pine Key?

Four-legged friends are welcome in Big Pine Key. Choose from more than 130 vacation rentals for guests traveling with pets.

How much does it cost to stay in house rentals in Big Pine Key?

Experience the best of Big Pine Key with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do house rentals in Big Pine Key have a bbq area?

Absolutely! We offer over 50 house rentals with a bbq area in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Big Pine Key have a gym?

Absolutely! We offer over 10 house rentals with a gym in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Big Pine Key have self check-in?

Absolutely! We offer over 30 house rentals with self check-in in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Big Pine Key have wifi?

Absolutely! We offer over 170 house rentals with wifi in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.

Are there Big Pine Key house rentals on Airbnb with pools?

Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Big Pine Key, available on Airbnb. Make a splash and soak up the sun in style!

Are there family-friendly house rentals in Big Pine Key?

Big Pine Key has more than 160 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

What are the most popular amenities for House Rentals in Big Pine Key?

Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with self check-in, over 170 homes with wifi, over 50 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Big Pine Key vacation rentals

Book unique cottages, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Big Pine Key

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Condo in Tavernier

4.86 out of 5 average rating, 268 reviews

Condo in the Keys, Peaceful ocean view retreat!

Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key West, this condo is close to state parks and coral reefs great for diving, fishing, and snorkeling. Relax on the private beach where kayak and paddle board rentals are available. Then enjoy a stroll on the pier to the gazebo. Splash around in the beautifully renovated heated pool and hot tub with mermaid bar! You can also enjoy food and beverages in the on-site cafe and bar

Guest favorite

Cottage in Marathon

4.96 out of 5 average rating, 24 reviews

Catch n' Relax Canalfront Cottage in Marathon

Enjoy our cottage right on a deep canal with 50' dock. Step right into your boat to fish the Atlantic Ocean & Gulf or just relax & enjoy the view! Enjoy an outdoor kitchen space for fish fry & Happy Hour drinks. Tan on our loungers or enjoy dinner under the stars. Kayaks/Bikes for you too. A Perfect location Minutes from Airport, 7Mile Bridge, Sombrero Beach & other Attractions. Close to shops & restaurants. Easily launch your boat from a free public marina nearby. Rental License #VACA-22-85

Guest favorite

Condo in Tavernier

4.96 out of 5 average rating, 174 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 105 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Guest favorite

Rental unit in Key Largo

4.92 out of 5 average rating, 132 reviews

2/1 Oceanfront Apartment with Dockage

The Seaside Vista is a luxurious ocean front retreat located in Key Largo. Only 1 hour from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From great dining, to water sports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled , enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer. MC Permit #: 21302180

Guest favorite

Rental unit in Marathon

5 out of 5 average rating, 10 reviews

"O" Fish Ally Paradise @Ocean Isle Fishing Village

Enjoy our unique condo, great for snowbirds or families. Located in Ocean Isles Fishing Village! Gorgeous skies right from the balcony. On property there is a heated pool, fishing dock, and a club house. The kitchen is fully equipped. This condo has air conditioning and heat. A 75 inch tv and free Wi-Fi. 1st floor has the kitchen, living room and bathroom. Upstairs is the bedroom with a Queen bed, bathroom with walk in shower and balcony. Separate area with queen bed large hall closet.

Guest favorite

Home in Marathon

5 out of 5 average rating, 18 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Superhost

Home in Cudjoe Key

5 out of 5 average rating, 14 reviews

Venture Out- Million Dollar Island Resort

Oceanfront Home, Pool Access/50 Ft Dock Fresh & Fabulous best describes this island listing . This fantastic Ocean home is in a Island resort community that is one the most unique places in the world. The stylish 2 Bedrooms, King or 2 Twins & living area will make your stay in Paradise one to remember. Deep water dock so in minutes you can visit tropical islands by boat or kayak . Enjoy the two Pools/ Resort amenities or just BBQ & fish off your dock. Resort one time fee $125

Superhost

Rental unit in Key West

4.76 out of 5 average rating, 138 reviews

Key West - Cool Shade ❀ The Green House

Unique and beautiful apartments in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen, your own garden. Best location for exploring Key West. The Green House is in the epicenter of Old-Town, with all attractions. One corner from world-famous Sloppy Joe's (Hemingway's favorite place) and Duval Loop, the free local ride, stops on Caroline street, next to the house.

Superhost

Home in Marathon

5 out of 5 average rating, 5 reviews

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort featuring 13 luxury vacation homes, 74 private marina slips and a centrally located pool deck and clubhouse. We provide unparalleled service in an intimate setting allowing you to relax and unwind. We are located in Marathon in The Middle Keys, so you can easily explore all that The Keys have to offer.

Guest favorite

Home in Cudjoe Key

4.82 out of 5 average rating, 11 reviews

Blue Vacation Home. Free cancellation policy

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. We provide bedding, towels, pots and pans. Vacation home sits far off of the main road for a great quiet vacation. We have 2 other properties with fantastic reviews that sit next to this vacation home.

Superhost

Condo in Tavernier

4.76 out of 5 average rating, 345 reviews

Florida Keys Getaway - Slps 4 - Ocean View

Check out this recently remodeled 1-bedroom condo with relaxing and tasteful beach decor - perfect for your Keys Getaway. Ideally located between Key Largo and Islamorada, it offers the best of both worlds! Ocean Pointe is an oceanfront condo property that's just steps away from all the Keys have to offer - the world's best fishing, diving, snorkeling, paddle boarding, and kayaking.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Big Pine Key vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Big Pine Key's top sights

No Name Pub54 locals recommend

Boondocks Grille and Draft House and Miniature Golf50 locals recommend

Looe Key Reef Resort & Dive Center33 locals recommend

Kiki's Sandbar Bar & Grille28 locals recommend

National Key Deer Refuge24 locals recommend

Big Pine Rooster16 locals recommend

Big Pine Key cottage rentals

Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 59 reviews

Islamorada bungalow 2 bed & pool

Guest favorite

Cottage in Little Torch Key

4.9 out of 5 average rating, 156 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Guest favorite

Cottage in Islamorada

4.96 out of 5 average rating, 26 reviews

Waterfront Cottage Walk to World Famous Lorelei

Guest favorite

Cottage in Key West

5 out of 5 average rating, 23 reviews

Pete's West Cottage steps from Duval

Superhost

Cottage in Cudjoe Key

4.86 out of 5 average rating, 35 reviews

Tidewater Views at Venture Out

Guest favorite

Cottage in Cudjoe Key

4.92 out of 5 average rating, 101 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Guest favorite

Cottage in Islamorada

4.98 out of 5 average rating, 93 reviews

2br/1ba w pool, 5 mins to beach and robbies marina

Superhost

Cottage in Key West

4.9 out of 5 average rating, 111 reviews

The Dancing Rooster

Show all

Big Pine Key cabin rentals

Cabin in Key West

4.56 out of 5 average rating, 107 reviews

Downtown 2BR Dog Friendly | Hot Tub | Deck

Superhost

Private room in Marathon

4.63 out of 5 average rating, 16 reviews

Viamarhe Cabin-Private beach, Kayak, yard games

Superhost

Cabin in Big Pine Key

4.63 out of 5 average rating, 19 reviews

2 Bedroom Turquoise Cabin

Superhost

Cabin in Big Pine Key

4.68 out of 5 average rating, 73 reviews

2 Bedroom Pink Cabin Half/Duplex # 11

Superhost

Cabin in Big Pine Key

4.55 out of 5 average rating, 20 reviews

1 Bedroom Cabin Half/Duplex Unit B up on Stilts

Cabin in Key West

4.72 out of 5 average rating, 86 reviews

Rustic 4BR Dog Friendly | Hot Tub | Deck

Guest favorite

Cabin in Key West

4.82 out of 5 average rating, 11 reviews

Living life Dockside

Show all

Big Pine Key condo rentals

Superhost

Condo in Tavernier

4.9 out of 5 average rating, 125 reviews

1BR - Key Largo Sun & Sand Hideaway

Superhost

Condo in Tavernier

4.87 out of 5 average rating, 139 reviews

Reel Large END Unit in Ocean Point Suites

Guest favorite

Condo in Tavernier

4.94 out of 5 average rating, 125 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Superhost

Condo in Tavernier

4.77 out of 5 average rating, 69 reviews

Pelican Bend Paradise [Ocean Pointe 4215]

Superhost

Condo in Key West

4.87 out of 5 average rating, 93 reviews

Key Wes't Best- Upgraded condo 5 mins to Smathers

Superhost

Condo in Key Colony Beach

4.9 out of 5 average rating, 145 reviews

Ocean Blue Condo, Key Colony Beach Heated Pool

Guest favorite

Condo in Key West

4.94 out of 5 average rating, 114 reviews

Fully renovated 2/2 bath condo w/ shared pool!

Guest favorite

Condo in Tavernier

5 out of 5 average rating, 31 reviews

Key Largo Sunrise Resort Style | Ocean Pointe 5315

Show all

Quick stats about vacation rentals in Big Pine Key

Total rentals
240 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
4.4K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with a pool
100 properties have a pool

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Big Pine Key?
Yes! Work meets play with ease at over 90 vacation rentals in Big Pine Key featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Big Pine Key?
Four-legged friends are welcome in Big Pine Key. Choose from more than 130 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Big Pine Key?
Experience the best of Big Pine Key with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Big Pine Key have a bbq area?
Absolutely! We offer over 50 house rentals with a bbq area in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Big Pine Key have a gym?
Absolutely! We offer over 10 house rentals with a gym in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Big Pine Key have self check-in?
Absolutely! We offer over 30 house rentals with self check-in in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Big Pine Key have wifi?
Absolutely! We offer over 170 house rentals with wifi in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Are there Big Pine Key house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Big Pine Key, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Big Pine Key?
Big Pine Key has more than 160 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Big Pine Key?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with self check-in, over 170 homes with wifi, over 50 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Big Pine Key vacation rentals

Top-rated vacation rentals in Big Pine Key

Vacation rentals for every style

Cottages

Houses

Cabins

Popular amenities for Big Pine Key vacation rentals

Stay near Big Pine Key's top sights

Big Pine Key cottage rentals

Cottage in Islamorada

Cottage in Little Torch Key

Cottage in Islamorada

Cottage in Key West

Cottage in Cudjoe Key

Cottage in Cudjoe Key

Cottage in Islamorada

Cottage in Key West

Big Pine Key cabin rentals

Cabin in Key West

Private room in Marathon

Cabin in Big Pine Key

Cabin in Big Pine Key

Cabin in Big Pine Key

Cabin in Key West

Cabin in Key West

Big Pine Key condo rentals

Condo in Tavernier

Condo in Tavernier

Condo in Tavernier

Condo in Tavernier

Condo in Key West

Condo in Key Colony Beach

Condo in Key West

Condo in Tavernier

Quick stats about vacation rentals in Big Pine Key

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Frequently Asked Questions

Destinations to explore