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.

Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 130 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!

Dec 28 – Jan 4

R14,319 ZAR per night
Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 140 reviews

Casa 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

R3,681 ZAR per night
Superhost

Home in Cudjoe Key

4.91 out of 5 average rating, 102 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.

Jul 6 – 13

R7,563 ZAR per night

Popular amenities for Big Pine Key vacation rentals

Stay near Big Pine Key's top sights

No Name Pub54 locals recommend
Little Palm Island Resort & Spa9 locals recommend
Kiki's Sandbar Bar & Grille28 locals recommend
National Key Deer Refuge24 locals recommend
Big Pine Rooster16 locals recommend
Big Pine Key Park4 locals recommend

Big Pine Key cottage rentals

Guest favorite

Cottage in Islamorada

4.85 out of 5 average rating, 124 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Nov 16 – 23

R3,703 ZAR per night
Superhost

Cottage in Key West

4.95 out of 5 average rating, 84 reviews

Mango Cottage 2 bedroom 2 bath with private pool

Oct 1 – 8

R12,922 ZAR per night
Guest favorite

Cottage in Marathon

4.95 out of 5 average rating, 20 reviews

Catch n' Relax Canalfront Cottage in Marathon

Nov 24 – Dec 1

R5,522 ZAR per night
Guest favorite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 74 reviews

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

Feb 24 – Mar 3

R15,779 ZAR per night
Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Sep 5 – 12

R5,136 ZAR per night
Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 63 reviews

Islamorada 2BR, 1BA w/ heated pool and firepit

Aug 5 – 12

R7,347 ZAR per night
Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 36 reviews

Islamorada bungalow 2 bed & pool

Sep 18 – 25

R8,161 ZAR per night
Superhost

Cottage in Cudjoe Key

4.94 out of 5 average rating, 52 reviews

Turtle Cove Views @ Venture Out - Waterfront

Feb 25 – Mar 4

R18,671 ZAR per night
Superhost

Cottage in Key West

4.86 out of 5 average rating, 28 reviews

Namaste: A blissful one bedroom cottage

Oct 26 – Nov 2

R15,240 ZAR per night
Guest favorite

Cottage in Key West

4.89 out of 5 average rating, 89 reviews

The Dancing Rooster

Feb 9 – 16

R12,637 ZAR per night
Guest favorite

Cottage in Marathon

4.96 out of 5 average rating, 25 reviews

WATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE

Jan 23 – 30

R10,589 ZAR per night

Cottage in Key West

4.74 out of 5 average rating, 336 reviews

1 bedroom Cottage

Apr 10 – 17

R6,890 ZAR per night

Big Pine Key condo rentals

Guest favorite

Condo in Marathon

4.87 out of 5 average rating, 183 reviews

Sombrero Beach Tropical Getaway

Sep 16 – 23

R4,444 ZAR per night
Guest favorite

Condo in Key West

4.85 out of 5 average rating, 124 reviews

A Perfect Getaway

Oct 1 – 8

R8,423 ZAR per night
Guest favorite

Condo in Key West

4.88 out of 5 average rating, 137 reviews

Large waterfront 2/2 end unit with boat slip

Nov 9 – 16

R14,558 ZAR per night
Guest favorite

Condo in Key West

4.85 out of 5 average rating, 142 reviews

Anchor Drop modern elegance upgrades throughout vi

Aug 11 – 18

R9,815 ZAR per night
Guest favorite

Condo in Key West

4.83 out of 5 average rating, 237 reviews

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

Mar 21 – 28

R9,558 ZAR per night
Guest favorite

Condo in Key Colony Beach

5.0 out of 5 average rating, 26 reviews

Sea-Esta Condo beach and pool

Aug 31 – Sep 7

R4,379 ZAR per night
Guest favorite

Condo in Marathon

4.93 out of 5 average rating, 14 reviews

Paradise @ MM61 - Waterfront 1 BR / 1 Bath Condo

Dec 14 – 21

R3,617 ZAR per night
Guest favorite

Condo in Marathon

5.0 out of 5 average rating, 5 reviews

Oceanside Spacious Studio Escape

Jul 1 – 8

R3,759 ZAR per night
Guest favorite

Condo in Marathon

5.0 out of 5 average rating, 11 reviews

Paradise Palms NEW 1B/2B Desk; Pool; Balcony

Jun 9 – 16

R4,324 ZAR per night
Superhost

Condo in Marathon

5.0 out of 5 average rating, 3 reviews

Salt Life: Experience Coastal Luxury, 2BR KCB

Sep 8 – 15

R6,830 ZAR per night
Guest favorite

Condo in Key West

4.99 out of 5 average rating, 83 reviews

Hidden Beach Duplex, Best Place in Key West

Aug 2 – 9

R13,128 ZAR per night
Guest favorite

Condo in Marathon

4.95 out of 5 average rating, 60 reviews

On the water, Pool, Tiki Bar, Beach Nearby!

Apr 5 – 12

R6,642 ZAR per night

Other great vacation rentals in Big Pine Key

Guest favorite

Home in Marathon

4.99 out of 5 average rating, 103 reviews

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

Jan 22 – 29

R12,588 ZAR per night
Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Nov 20 – 27

R2,235 ZAR per night
Guest favorite

Camper/RV in Big Pine Key

4.91 out of 5 average rating, 34 reviews

Having fun in the lower Keys

Jul 31 – Aug 7

R3,118 ZAR per night
Guest favorite

Camper/RV in Big Pine Key

4.92 out of 5 average rating, 38 reviews

You’re on island time at The Island Girl

May 26 – Jun 2

R3,842 ZAR per night
Guest favorite

Camper/RV in Big Pine Key

4.94 out of 5 average rating, 34 reviews

Delightful 1 bedroom camper with pool

Jul 8 – 15

R3,330 ZAR per night
Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 81 reviews

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

May 3 – 10

R3,405 ZAR per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Nov 9 – 16

R10,598 ZAR per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

Jun 7 – 14

R2,839 ZAR per night
Guest favorite

Home in Key Colony Beach

4.98 out of 5 average rating, 44 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Oct 1 – 8

R4,693 ZAR per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

Oct 12 – 19

R14,768 ZAR per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 38 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Jul 29 – Aug 5

R14,103 ZAR per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 29 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

Oct 23 – 30

R9,495 ZAR per night

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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Big Pine Key