Holiday rentals near Big Pine Key Flea Market
We found 1,283 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Big Pine Key Flea Market, scroll through and discover holiday rentals to choose your home away from home. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, such as air conditioning and a TV. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Big Pine Key Flea Market
Showing deals for:8 Aug - 15 Aug
Image gallery for A Tropical Luxury Getaway, Your own private resort!!
1010 out of 10 rating
Exceptional
(34 reviews)
A Tropical Luxury Getaway, Your own private resort!!
Summerland Key, FL
8% off
Price is NZ$35,872
NZ$35,872
NZ$5,125 per night
includes taxes & fees
Image gallery for 2 Bedroom 2.5 Bath Luxury Townhome in the Keys
9.69.6 out of 10 rating
Exceptional
(35 reviews)
2 Bedroom 2.5 Bath Luxury Townhome in the Keys
Summerland Key, FL
8% off
Price is NZ$5,454
NZ$5,454
NZ$779 per night
includes taxes & fees
Image gallery for Water View Town Home
8.88.8 out of 10 rating
Excellent
(5 reviews)
Water View Town Home
Summerland Key, FL
8% off
Price is NZ$5,454
NZ$5,454
NZ$779 per night
includes taxes & fees
Image gallery for 2 Bedroom 2 Bathroom Home with Private Pool Walking Distance to a Water View
9.09.0 out of 10 rating
Wonderful
(26 reviews)
2 Bedroom 2 Bathroom Home with Private Pool Walking Distance to a Water View
Summerland Key, FL
8% off
Price is NZ$5,454
NZ$5,454
NZ$779 per night
includes taxes & fees
Image gallery for A slice of paradise
9.09.0 out of 10 rating
Wonderful
(95 reviews)
A slice of paradise
Summerland Key, FL
8% off
Price is NZ$3,079
NZ$3,079
NZ$440 per night
includes taxes & fees
Image gallery for Tropical Retreat in the Heart of the Keys
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Tropical Retreat in the Heart of the Keys
Marathon, FL
8% off
Price is NZ$5,063
NZ$5,063
NZ$723 per night
includes taxes & fees
Image gallery for Private Secluded Ocean View & Pool Near Key West
8.48.4 out of 10 rating
Very good
(90 reviews)
Private Secluded Ocean View & Pool Near Key West
Summerland Key, FL
8% off
Price is NZ$8,822
NZ$8,822
NZ$1,260 per night
includes taxes & fees
Image gallery for *Snowbirds Paradise*
1010 out of 10 rating
Exceptional
(7 reviews)
*Snowbirds Paradise*
Marathon, FL
7% off
Price is NZ$2,909
NZ$2,909
NZ$416 per night
includes taxes & fees
Image gallery for Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244
Marathon, FL
8% off
Price is NZ$4,033
NZ$4,033
NZ$576 per night
includes taxes & fees
Image gallery for Fishermen’s Paradise
9.29.2 out of 10 rating
Wonderful
(95 reviews)
Fishermen’s Paradise
Summerland Key, FL
8% off
Price is NZ$3,463
NZ$3,463
NZ$495 per night
includes taxes & fees
Image gallery for WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
1010 out of 10 rating
Exceptional
(9 reviews)
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
Summerland Key, FL
8% off
Price is NZ$8,548
NZ$8,548
NZ$1,221 per night
includes taxes & fees
Image gallery for Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.89.8 out of 10 rating
Exceptional
(231 reviews)
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Summerland Key, FL
8% off
Price is NZ$5,759
NZ$5,759
NZ$823 per night
includes taxes & fees
Image gallery for Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Summerland Key, FL
8% off
Price is NZ$4,653
NZ$4,653
NZ$665 per night
includes taxes & fees
Image gallery for NAUTILUS...ocean front cottage retreat ~
8.48.4 out of 10 rating
Very good
(5 reviews)
NAUTILUS...ocean front cottage retreat ~
Summerland Key, FL
8% off
Price is NZ$8,265
NZ$8,265
NZ$1,181 per night
includes taxes & fees
Image gallery for ATLANTIS...Ocean Front Cottage Retreat!
9.89.8 out of 10 rating
Exceptional
(13 reviews)
ATLANTIS...Ocean Front Cottage Retreat!
Summerland Key, FL
5% off
Price is NZ$12,910
NZ$12,910
NZ$1,844 per night
includes taxes & fees
Image gallery for Bay View 2 Bed / 2.5 Bath Vacation Townhome Rental in Key West Area
9.89.8 out of 10 rating
Exceptional
(82 reviews)
Bay View 2 Bed / 2.5 Bath Vacation Townhome Rental in Key West Area
Summerland Key, FL
8% off
Price is NZ$5,454
NZ$5,454
NZ$779 per night
includes taxes & fees
Image gallery for 2 Bedroom 2.5 Bath Luxury Townhome 26 Miles from Downtown Key West
9.69.6 out of 10 rating
Exceptional
(27 reviews)
2 Bedroom 2.5 Bath Luxury Townhome 26 Miles from Downtown Key West
Summerland Key, FL
8% off
Price is NZ$5,454
NZ$5,454
NZ$779 per night
includes taxes & fees
Image gallery for Enjoy Caribbean weather in the USA. Openings in May 2025!! Book now!
9.49.4 out of 10 rating
Exceptional
(137 reviews)
Enjoy Caribbean weather in the USA. Openings in May 2025!! Book now!
Summerland Key, FL
8% off
Price is NZ$4,229
NZ$4,229
NZ$604 per night
includes taxes & fees
Image gallery for Luxury Ocean View 2 Bed / 2.5 Bath Townhome in the Keys
9.69.6 out of 10 rating
Exceptional
(50 reviews)
Luxury Ocean View 2 Bed / 2.5 Bath Townhome in the Keys
Summerland Key, FL
8% off
Price is NZ$5,454
NZ$5,454
NZ$779 per night
includes taxes & fees
Image gallery for Connecting 2 Bed / 2.5 Bath Luxry Townhomes w/Seperate Entrances - Can Sleep 12
9.69.6 out of 10 rating
Exceptional
(30 reviews)
Connecting 2 Bed / 2.5 Bath Luxry Townhomes w/Seperate Entrances - Can Sleep 12
Summerland Key, FL
8% off
Price is NZ$10,868
NZ$10,868
NZ$1,553 per night
includes taxes & fees
Image gallery for waterfront cottage near key west, sleeps 6
9.49.4 out of 10 rating
Exceptional
(22 reviews)
waterfront cottage near key west, sleeps 6
Summerland Key, FL
7% off
Price is NZ$3,821
NZ$3,821
NZ$546 per night
includes taxes & fees
Image gallery for Water View Town home
1010 out of 10 rating
Exceptional
(11 reviews)
Water View Town home
Summerland Key, FL
8% off
Price is NZ$5,454
NZ$5,454
NZ$779 per night
includes taxes & fees
Image gallery for Lower Keys paradise
1010 out of 10 rating
Exceptional
(32 reviews)
Lower Keys paradise
Summerland Key, FL
8% off
Price is NZ$4,059
NZ$4,059
NZ$580 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Big Pine Key Flea Market
430 Empty RV Lot with 35' Seawall
Sleeps 6 · 1 bathroom
Cozy RV in campground in Beautiful Big Pine Key!
Sleeps 4 · 1 bedroom · 1 bathroom
Captains Quarters: Charming 3-Bed/2-Bath Home with Convenient Boot Key Harbor
Sleeps 8 · 3 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
4 reviews(4 reviews)
Dreamy waterfront getaway with private pool, kayak, bikes, fast WiFi & gas grill
Sleeps 8 · 3 bedrooms · 2+ bathrooms
7.47.4 out of 10
Goodgood
8 reviews(8 reviews)
Angler`s Retreat: Updated 3-Bed/2-Bath Home with Dockage
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Private paradise! Gorgeous 4/3 Half duplex w/ private pool & dockage!
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value