Vacation rentals in Pine Key

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pine Key

Guests agree: these stays 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

$660 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 .

Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.

Nov 20 – 27

$102 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

$169 per night

Popular amenities for Pine Key vacation rentals

Other great vacation rentals in Pine Key

Superhost

Houseboat in Marathon

4.82 out of 5 average rating, 56 reviews

Houseboat Getaway In Marathon

Feb 11 – 18

$237 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 6 – 13

$142 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

$485 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 9 – 16

$153 per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

Jun 8 – 15

$131 per night
Superhost

Home in Cudjoe Key

4.85 out of 5 average rating, 39 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Jun 4 – 11

$569 per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

Oct 12 – 19

$675 per night
Guest favorite

Home in Marathon

4.9 out of 5 average rating, 52 reviews

Beautiful Beachfront Home w/ Pool/Tiki/Dock

Sep 19 – 26

$599 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

$608 per night
Superhost

Home in Upper Sugarloaf Key

4.86 out of 5 average rating, 43 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Dec 6 – 13

$774 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

Sep 2 – 9

$176 per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 19 reviews

Paradise in the Keys

Oct 1 – 8

$750 per night

Destinations to explore

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