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.
Cottage in Cudjoe Key
4.92 out of 5 average rating, 130 reviewsATLANTIS...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!
Dec 28 – Jan 4
Guest suite in Marathon
4.98 out of 5 average rating, 140 reviewsCasa Mariposa: Sombrero Beach Neighborhood
Book your 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, selected as 1 0f 24 amazing AirBNB rentals in the Keys, and 1 of 23 Amazing Airbnbs in The Keys. Step out the door from your private suite to a coral path that leads to our 50' heated/cooled lap pool, waterfall and large patio. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in an other lengths of stay.
May 3 – 10
Home in Cudjoe Key
4.91 out of 5 average rating, 102 reviewsSunrise 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.
Jul 6 – 13
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Big Pine Key vacation rentals
Big Pine Key cottage rentals
Cottage in Islamorada
4.85 out of 5 average rating, 124 reviews1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Nov 16 – 23
Cottage in Key West
4.95 out of 5 average rating, 84 reviewsMango Cottage 2 bedroom 2 bath with private pool
Oct 1 – 8
Cottage in Marathon
4.95 out of 5 average rating, 20 reviewsCatch n' Relax Canalfront Cottage in Marathon
Nov 24 – Dec 1
Cottage in Cudjoe Key
4.91 out of 5 average rating, 74 reviewsKing Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Feb 24 – Mar 3
Cottage in Islamorada
4.94 out of 5 average rating, 16 reviewsWaterfront Cottage Walk to World Famous Lorelei
Sep 5 – 12
Cottage in Islamorada
4.97 out of 5 average rating, 63 reviewsIslamorada 2BR, 1BA w/ heated pool and firepit
Aug 5 – 12
Cottage in Islamorada
4.94 out of 5 average rating, 36 reviewsIslamorada bungalow 2 bed & pool
Sep 18 – 25
Cottage in Cudjoe Key
4.94 out of 5 average rating, 52 reviewsTurtle Cove Views @ Venture Out - Waterfront
Feb 25 – Mar 4
Cottage in Key West
4.86 out of 5 average rating, 28 reviewsNamaste: A blissful one bedroom cottage
Oct 26 – Nov 2
Cottage in Key West
4.89 out of 5 average rating, 89 reviewsThe Dancing Rooster
Feb 9 – 16
Cottage in Marathon
4.96 out of 5 average rating, 25 reviewsWATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
Jan 23 – 30
Cottage in Key West
4.74 out of 5 average rating, 336 reviews1 bedroom Cottage
Apr 10 – 17
Big Pine Key condo rentals
Condo in Marathon
4.87 out of 5 average rating, 183 reviewsSombrero Beach Tropical Getaway
Sep 16 – 23
Condo in Key West
4.85 out of 5 average rating, 124 reviewsA Perfect Getaway
Oct 1 – 8
Condo in Key West
4.88 out of 5 average rating, 137 reviewsLarge waterfront 2/2 end unit with boat slip
Nov 9 – 16
Condo in Key West
4.85 out of 5 average rating, 142 reviewsAnchor Drop modern elegance upgrades throughout vi
Aug 11 – 18
Condo in Key West
4.83 out of 5 average rating, 237 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
Mar 21 – 28
Condo in Key Colony Beach
5.0 out of 5 average rating, 26 reviewsSea-Esta Condo beach and pool
Aug 31 – Sep 7
Condo in Marathon
4.93 out of 5 average rating, 14 reviewsParadise @ MM61 - Waterfront 1 BR / 1 Bath Condo
Dec 14 – 21
Condo in Marathon
5.0 out of 5 average rating, 5 reviewsOceanside Spacious Studio Escape
Jul 1 – 8
Condo in Marathon
5.0 out of 5 average rating, 11 reviewsParadise Palms NEW 1B/2B Desk; Pool; Balcony
Jun 9 – 16
Condo in Marathon
5.0 out of 5 average rating, 3 reviewsSalt Life: Experience Coastal Luxury, 2BR KCB
Sep 8 – 15
Condo in Key West
4.99 out of 5 average rating, 83 reviewsHidden Beach Duplex, Best Place in Key West
Aug 2 – 9
Condo in Marathon
4.95 out of 5 average rating, 60 reviewsOn the water, Pool, Tiki Bar, Beach Nearby!
Apr 5 – 12
Other great vacation rentals in Big Pine Key
Home in Marathon
4.99 out of 5 average rating, 103 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Jan 22 – 29
Tiny home in Big Pine Key
4.8 out of 5 average rating, 88 reviewsBreezy pines 28 foot 5th wheel trailer .
Nov 20 – 27
Camper/RV in Big Pine Key
4.91 out of 5 average rating, 34 reviewsHaving fun in the lower Keys
Jul 31 – Aug 7
Camper/RV in Big Pine Key
4.92 out of 5 average rating, 38 reviewsYou’re on island time at The Island Girl
May 26 – Jun 2
Camper/RV in Big Pine Key
4.94 out of 5 average rating, 34 reviewsDelightful 1 bedroom camper with pool
Jul 8 – 15
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 81 reviewsTurtle-By-The-Sea: the Best Deal in KCB!
May 3 – 10
Home in Marathon
4.97 out of 5 average rating, 31 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Nov 9 – 16
Home in Marathon
4.97 out of 5 average rating, 31 reviewsThe Gulf Cottage at Marathon Key
Jun 7 – 14
Home in Key Colony Beach
4.98 out of 5 average rating, 44 reviewsCaptain’s Quarters Ahoy Mateys! Florida, Keys
Oct 1 – 8
Home in Marathon
5.0 out of 5 average rating, 8 reviewsMillion Dollar View
Oct 12 – 19
Home in Cudjoe Key
4.84 out of 5 average rating, 38 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Jul 29 – Aug 5
Home in Marathon
5.0 out of 5 average rating, 29 reviews100' Dockage, Pool, Kayaks, Paddle Board, Bikes!
Oct 23 – 30
Quick stats about vacation rentals in Big Pine Key
Total rentals | 220 properties |
---|---|
Rentals with a pool | 90 properties have a pool |
Pet-friendly rentals | 110 properties allow pets |
Family-friendly rentals | 170 properties are a good fit for families |
Total number of reviews | 3.8K reviews |
Nightly prices starting at | R947 ZAR 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 80 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 90 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 house rentals in Big Pine Key?
Experience the best of Big Pine Key with our house rentals, starting at about $70 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 houseboat rentals in Big Pine Key have free parking?
Absolutely! We offer over 10 houseboat rentals with free parking 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.
Are there family-friendly house rentals in Big Pine Key?
Big Pine Key has more than 140 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 40 homes with self check-in, over 140 homes with free parking, over 10 homes with a gym, over 50 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Rentals with a kayak Big Pine Key
- Rentals with a washer and dryer Big Pine Key
- Fitness-friendly rentals Big Pine Key
- Rentals with pools Big Pine Key
- Rentals with beach access Big Pine Key
- Pet-friendly rentals Big Pine Key
- Rentals with a fire pit Big Pine Key
- Cabin rentals Big Pine Key
- Rentals with a patio Big Pine Key
- Kid-friendly rentals Big Pine Key
- Monthly Rentals Big Pine Key
- House rentals Big Pine Key
- Waterfront rentals Big Pine Key
- Rentals with outdoor seating Big Pine Key
- Family-friendly rentals Big Pine Key
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