Holiday rentals near Florida Keys Wilderness
We found 5,042 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals within easy reach of Florida Keys Wilderness that can be your home away from home. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Florida Keys Wilderness
Showing deals for:15 Aug - 22 Aug
Image gallery for Private, Gated, Oceanfront, Beachfront 5-Star Estate with dock, putting green.
1010 out of 10 rating
Exceptional
(73 reviews)
Private, Gated, Oceanfront, Beachfront 5-Star Estate with dock, putting green.
Marathon, FL
8% off
Price is NZ$20,665
NZ$20,665
NZ$2,952 per night
includes taxes & fees
Image gallery for "Tranquility " At Ann Street Gardens Steps From Duval
1010 out of 10 rating
Exceptional
(78 reviews)
"Tranquility " At Ann Street Gardens Steps From Duval
Key West, FL
8% off
Price is NZ$6,864
NZ$6,864
NZ$981 per night
includes taxes & fees
Image gallery for Steps from Duval with Private Pool – Southern Palms
8.08.0 out of 10 rating
Very good
(7 reviews)
Steps from Duval with Private Pool – Southern Palms
Key West, Florida
8% off
Price is NZ$28,080
NZ$28,080
NZ$4,011 per night
includes taxes & fees
Image gallery for Old Town Bali Hideaway For 2, Just Steps From Duval
1010 out of 10 rating
Exceptional
(88 reviews)
Old Town Bali Hideaway For 2, Just Steps From Duval
Key West, Fl
8% off
Price is NZ$5,571
NZ$5,571
NZ$796 per night
includes taxes & fees
Image gallery for The Cathouse, an Old Town tropical poolside oasis with huge, heated pool
1010 out of 10 rating
Exceptional
(9 reviews)
The Cathouse, an Old Town tropical poolside oasis with huge, heated pool
Key West, FL
9% off
Price is NZ$12,923
NZ$12,923
NZ$1,846 per night
includes taxes & fees
Image gallery for Parking, Pet Friendly, Pool, Dock - Suncoast House
9.69.6 out of 10 rating
Exceptional
(36 reviews)
Parking, Pet Friendly, Pool, Dock - Suncoast House
Key West, Florida
8% off
Price is NZ$24,208
NZ$24,208
NZ$3,458 per night
includes taxes & fees
Image gallery for Ocean views! <br>Luxury suites
1010 out of 10 rating
Exceptional
(26 reviews)
Ocean views! <br>Luxury suites
Key West, FL
11% off
Price is NZ$6,956
NZ$6,956
NZ$994 per night
includes taxes & fees
Image gallery for Parking, Pet Friendly, Pool & Dock - Aquaria House
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Parking, Pet Friendly, Pool & Dock - Aquaria House
Key West, Florida
8% off
Price is NZ$19,315
NZ$19,315
NZ$2,759 per night
includes taxes & fees
Image gallery for Key West 44ft Sailboat Wild Thing-Summer Fun Sandbar Motorboat Trips
9.49.4 out of 10 rating
Exceptional
(76 reviews)
Key West 44ft Sailboat Wild Thing-Summer Fun Sandbar Motorboat Trips
Key West, FL
8% off
Price is NZ$6,598
NZ$6,598
NZ$943 per night
includes taxes & fees
Image gallery for Pool View 3BR Residence | Beachside Resort
9.89.8 out of 10 rating
Exceptional
(47 reviews)
Pool View 3BR Residence | Beachside Resort
Key West, Florida
8% off
Price is NZ$9,318
NZ$9,318
NZ$1,331 per night
includes taxes & fees
Image gallery for Key West style cottage w/ dock overlooking Florida Bay. Wrap around windows!
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Key West style cottage w/ dock overlooking Florida Bay. Wrap around windows!
Marathon, FL
8% off
Price is NZ$5,074
NZ$5,074
NZ$725 per night
includes taxes & fees
Image gallery for The Hollinsed House "Victorian Delights" - Large 1 Bedroom
9.89.8 out of 10 rating
Exceptional
(122 reviews)
The Hollinsed House "Victorian Delights" - Large 1 Bedroom
Key West, FL
7% off
Price is NZ$3,636
NZ$3,636
NZ$519 per night
includes taxes & fees
Image gallery for Hollinsed House Poolside / King Studio / sleeps 2
9.69.6 out of 10 rating
Exceptional
(106 reviews)
Hollinsed House Poolside / King Studio / sleeps 2
Key West, FL
5% off
Price is NZ$3,533
NZ$3,533
NZ$505 per night
includes taxes & fees
Image gallery for Ocean Depth Room Barnacle Resort
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Ocean Depth Room Barnacle Resort
Big Pine Key, Florida
8% off
Price is NZ$5,984
NZ$5,984
NZ$855 per night
includes taxes & fees
Image gallery for Parking, Pool & Dock - Spindrift House
1010 out of 10 rating
Exceptional
(26 reviews)
Parking, Pool & Dock - Spindrift House
Key West, Florida
8% off
Price is NZ$19,145
NZ$19,145
NZ$2,735 per night
includes taxes & fees
Image gallery for Commodore's Compound - Epic Location Near Duval
9.09.0 out of 10 rating
Wonderful
(11 reviews)
Commodore's Compound - Epic Location Near Duval
Key West, Florida
8% off
Price is NZ$31,032
NZ$31,032
NZ$4,433 per night
includes taxes & fees
Image gallery for Access to Cabana Club/Private beach
1010 out of 10 rating
Exceptional
(8 reviews)
Access to Cabana Club/Private beach
Key Colony Beach, FL
7% off
Price is NZ$5,288
NZ$5,288
NZ$755 per night
includes taxes & fees
Image gallery for Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
9.69.6 out of 10 rating
Exceptional
(95 reviews)
Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
Marathon, FL
8% off
Price is NZ$8,024
NZ$8,024
NZ$1,146 per night
includes taxes & fees
Image gallery for Waterfront Island Escape with Private Plunge Pool
1010 out of 10 rating
Exceptional
(21 reviews)
Waterfront Island Escape with Private Plunge Pool
Marathon, FL
7% off
Price is NZ$4,450
NZ$4,450
NZ$636 per night
includes taxes & fees
Image gallery for BF Beach Front villa Pool Beach Dock Ocean Sleeps 6 W&D Kitchen Parking WiFi BBQ
9.49.4 out of 10 rating
Exceptional
(18 reviews)
BF Beach Front villa Pool Beach Dock Ocean Sleeps 6 W&D Kitchen Parking WiFi BBQ
Marathon, FL
30% off
Price is NZ$4,878
NZ$4,878
NZ$697 per night
includes taxes & fees
Image gallery for 3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel/Marina
1010 out of 10 rating
Exceptional
(44 reviews)
3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel/Marina
Key West, FL
8% off
Price is NZ$7,484
NZ$7,484
NZ$1,069 per night
includes taxes & fees
Image gallery for The Island Suite at KW Vacation
1010 out of 10 rating
Exceptional
(107 reviews)
The Island Suite at KW Vacation
Key West, FL
8% off
Price is NZ$3,695
NZ$3,695
NZ$528 per night
includes taxes & fees
Image gallery for NEW 4 Bedroom/3 Bath Home w/Private Pool,40 ft. Dock near Sombrero Beach!
1010 out of 10 rating
Exceptional
(59 reviews)
NEW 4 Bedroom/3 Bath Home w/Private Pool,40 ft. Dock near Sombrero Beach!
Marathon, FL
7% off
Price is NZ$7,853
NZ$7,853
NZ$1,122 per night
includes taxes & fees
Image gallery for Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location
1010 out of 10 rating
Exceptional
(49 reviews)
Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location
Key West, FL
7% off
Price is NZ$5,930
NZ$5,930
NZ$847 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Florida Keys Wilderness
Old Florida Style, wrap around porch, boat basin for dockage, open water
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
73 reviews(73 reviews)
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
204 reviews(204 reviews)
Direct Oceanfront Cottage-Sunrise View- #2,
Sleeps 4 · 2 bedrooms · 1 bathroom
8.68.6 out of 10
Excellentexcellent
176 reviews(176 reviews)
Ocean Front Access - just 30 miles to Key West
Sleeps 2 · 1 bedroom · 1 bathroom
8.28.2 out of 10
Very goodvery good
158 reviews(158 reviews)
Cottage with Pool and Boat Dockage just minutes to Key West!
Sleeps 2 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
138 reviews(138 reviews)
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Sleeps 6 · 2 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
231 reviews(231 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