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Big Pine Key vacation rentals

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Top-rated vacation rentals in Big Pine Key

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

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Cottage in Cudjoe Key

4.91 out of 5 average rating, 133 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

May 25 – Jun 1

G$159,291 GYD per night

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

May 5 – 12

G$45,298 GYD per night

Home in Cudjoe Key

4.9 out of 5 average rating, 104 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.

Apr 13 – 20

G$83,300 GYD per night

Cottage in Islamorada

4.85 out of 5 average rating, 124 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Sep 26 – Oct 3

G$38,183 GYD per night

Cottage in Little Torch Key

4.91 out of 5 average rating, 145 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!

Feb 12 – 19

G$112,796 GYD per night

Condo in Key Colony Beach

4.91 out of 5 average rating, 197 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Jul 28 – Aug 4

G$71,240 GYD per night

Villa in Marathon

4.89 out of 5 average rating, 145 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!

Mar 5 – 12

G$91,894 GYD per night

Home in Cudjoe Key

4.97 out of 5 average rating, 120 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Oct 5 – 12

G$69,481 GYD per night

Home in Marathon

4.99 out of 5 average rating, 106 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Aug 17 – 24

G$84,850 GYD per night

Home in Marathon

4.96 out of 5 average rating, 125 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Jul 10 – 17

G$100,957 GYD per night

Apartment in Key West

4.92 out of 5 average rating, 1034 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Sep 18 – 25

G$59,788 GYD per night

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise and Cudjoe Bay

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

Nov 13 – 20

G$84,352 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Big Pine Key vacation rentals

Laptop-friendly workspace

Stay near Big Pine Key's top sights

No Name Pub54 locals recommend

Little Palm Island Resort & Spa9 locals recommend

National Key Deer Refuge24 locals recommend

Kiki's Sandbar Bar & Grille28 locals recommend

Big Pine Rooster16 locals recommend

Big Pine Key Park4 locals recommend

Other great vacation rentals in Big Pine Key

Cottage in Marathon

4.95 out of 5 average rating, 22 reviews

Catch n' Relax Canalfront Cottage in Marathon

Oct 24 – 31

G$60,814 GYD per night

Cottage in Key West

4.95 out of 5 average rating, 84 reviews

Mango Cottage 2 bedroom 2 bath with private pool

Sep 18 – 25

G$139,434 GYD per night

Cottage in Cudjoe Key

4.91 out of 5 average rating, 79 reviews

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

Jan 29 – Feb 5

G$156,789 GYD per night

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Sep 1 – 8

G$57,581 GYD per night

Cottage in Islamorada

4.95 out of 5 average rating, 40 reviews

Islamorada bungalow 2 bed & pool

Aug 16 – 23

G$89,882 GYD per night

Cottage in Islamorada

4.97 out of 5 average rating, 66 reviews

Key Lime Cottage 2br 1ba w/pool

Nov 30 – Dec 7

G$77,377 GYD per night

Cottage in Key West

4.87 out of 5 average rating, 30 reviews

Namaste: A blissful one bedroom cottage

Jul 28 – Aug 4

G$132,153 GYD per night

Cottage in Cudjoe Key

4.84 out of 5 average rating, 32 reviews

Tidewater Views @ Venture Out - Waterfront

Jul 27 – Aug 3

G$100,110 GYD per night

Big Pine Key condo rentals

Condo in Marathon

4.87 out of 5 average rating, 191 reviews

Sombrero Beach Tropical Getaway

Oct 4 – 11

G$48,095 GYD per night

Condo in Key Colony Beach

4.8 out of 5 average rating, 107 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

Apr 5 – 12

G$69,889 GYD per night

Condo in Key West

4.86 out of 5 average rating, 129 reviews

A Perfect Getaway

May 26 – Jun 2

G$90,341 GYD per night

Condo in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

Feb 20 – 27

G$148,507 GYD per night

Condo in Key West

4.85 out of 5 average rating, 110 reviews

Rooftop Penthouse

Aug 21 – 28

G$122,270 GYD per night

Condo in Key West

4.83 out of 5 average rating, 243 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

Aug 20 – 27

G$55,357 GYD per night

Condo in Key West

4.85 out of 5 average rating, 143 reviews

Anchor Drop modern elegance upgrades throughout vi

Sep 15 – 22

G$101,471 GYD per night

Condo in Marathon

5.0 out of 5 average rating, 6 reviews

Oceanside Spacious Studio Escape

Aug 27 – Sep 3

G$40,513 GYD per night

Other great vacation rentals in Big Pine Key

Tiny home in Big Pine Key

4.8 out of 5 average rating, 89 reviews

Breezy pines 28 foot 5th wheel trailer .

Nov 12 – 19

G$22,589 GYD per night

Camper/RV in Big Pine Key

4.93 out of 5 average rating, 40 reviews

Having fun in the lower Keys

Jun 19 – 26

G$25,159 GYD per night

Camper/RV in Big Pine Key

4.92 out of 5 average rating, 37 reviews

Delightful 1 bedroom camper with pool

Jul 8 – 15

G$35,856 GYD per night

Home in Marathon

4.97 out of 5 average rating, 34 reviews

The Gulf Cottage at Marathon Key

Jul 14 – 21

G$28,313 GYD per night

Home in Marathon

4.97 out of 5 average rating, 32 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Dec 7 – 14

G$120,938 GYD per night

Home in Cudjoe Key

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

Oct 1 – 8

G$46,831 GYD per night

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 83 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

Jul 7 – 14

G$43,619 GYD per night

Boat in Key West

4.93 out of 5 average rating, 42 reviews

Sailboat in Luxury Marina

Jun 2 – 9

G$29,984 GYD per night

Quick stats about vacation rentals in Big Pine Key

Total rentals
230 properties
Rentals with a pool
100 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
190 properties are a good fit for families
Total number of reviews
4.4K reviews
Nightly prices starting at
G$10,428 GYD before taxes and fees

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 110 vacation rentals for guests traveling with pets.
Are there Big Pine Key vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 100 vacation homes with pools in Big Pine Key, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in rv rentals in Big Pine Key?
Experience the best of Big Pine Key with our rv rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Big Pine Key?
Big Pine Key has more than 190 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Big Pine Key have a bbq area?
Absolutely! We offer over 60 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 40 house rentals with self check-in in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Do houseboat rentals in Big Pine Key have wifi?
Absolutely! We offer over 10 houseboat rentals with wifi in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
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 160 homes with wifi, over 10 homes with a gym, over 40 homes with self check-in, over 60 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore