Vacation rentals in Big Pine Key

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Top-rated holiday rentals in Big Pine Key

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

Superhost
Cottage in Cudjoe Key
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!
8–15 Jan
$1,102 NZD per night
4.92 out of 5 average rating, 130 reviews
Superhost
Tiny home in Big Pine Key
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.
16–23 Nov
$227 NZD per night
4.8 out of 5 average rating, 88 reviews
Guest favourite
Home in Cudjoe Key
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.
11–18 Jul
$699 NZD per night
4.91 out of 5 average rating, 101 reviews

Popular amenities for Big Pine Key holiday 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

Other great holiday rentals in Big Pine Key

Guest favourite
Campervan/RV in Big Pine Key
You’re on island time at The Island Girl
17–24 Jun
$385 NZD per night
4.92 out of 5 average rating, 36 reviews
Guest favourite
Home in Marathon
Beach House, Private Pool & Dock, Gulf Sunset view
9–16 Nov
$1,096 NZD per night
4.97 out of 5 average rating, 31 reviews
Guest favourite
Guest suite in Key Colony Beach
Turtle-By-The-Sea: the Best Deal in KCB!
14–21 Jul
$402 NZD per night
4.99 out of 5 average rating, 80 reviews
Guest favourite
Home in Big Pine Key
Fishermen`s Paradise: Huge pool, 220-foot dock
3–10 Sep
$1,825 NZD per night
4.89 out of 5 average rating, 62 reviews
Superhost
Home in Cudjoe Key
*Emerald Seas*-Florida Keys Ocean Front Paradise!
17–24 Nov
$1,396 NZD per night
4.83 out of 5 average rating, 36 reviews
Guest favourite
Home in Cudjoe Key
May Extravaganza - Relax in Paradise!
1–8 Oct
$435 NZD per night
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Marathon
Million Dollar View
31 Aug – 7 Sep
$1,545 NZD per night
5.0 out of 5 average rating, 7 reviews
Superhost
Campervan/RV in Big Pine Key
TIKI HIDEAWAY ~ 2 Bedroom RV w/pool and gazebo
8–15 Jul
$401 NZD per night
4.92 out of 5 average rating, 49 reviews
Superhost
Home in Marathon
Oceanfront mermaid house pool and dock
27 Oct – 3 Nov
$1,056 NZD per night
4.93 out of 5 average rating, 56 reviews
Guest favourite
Condo in Key West
Hidden Beach Duplex, Best Place in Key West
17–24 Nov
$1,213 NZD per night
4.99 out of 5 average rating, 83 reviews
Guest favourite
Home in Key Colony Beach
Captain’s Quarters Ahoy Mateys! Florida, Keys
8–15 Oct
$525 NZD per night
4.98 out of 5 average rating, 43 reviews
Guest favourite
Home in Marathon
Beautiful Beachfront Home w/ Pool/Tiki/Dock
11–18 Sep
$1,332 NZD per night
4.9 out of 5 average rating, 52 reviews

Quick stats about holiday 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

$82 NZD before taxes and fees

Destinations to explore

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