Holiday rentals near Shark Key
We found 879 holiday rentals — enter your dates for availability
If you'd like to stay close to Shark Key, scroll through and discover holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the amenities that you expect and more, which might include Wi-Fi and a fireplace. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Shark Key
Showing deals for:31 Oct - 7 Nov
Image gallery for Waterfront, Private Heated Pool - Capmar House
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Waterfront, Private Heated Pool - Capmar House
Key West, Florida
8% off
Price is NZ$24,170
NZ$24,170
NZ$3,453 per night
includes taxes & fees
Image gallery for Parking, Heated Pool & Pet Friendly - Altair House
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Parking, Heated Pool & Pet Friendly - Altair House
Key West, Florida
8% off
Price is NZ$34,685
NZ$34,685
NZ$4,955 per night
includes taxes & fees
Image gallery for Parking, Pet Friendly, Pool, Dock - Suncoast House
9.69.6 out of 10 rating
Exceptional
(39 reviews)
Parking, Pet Friendly, Pool, Dock - Suncoast House
Key West, Florida
8% off
Price is NZ$34,325
NZ$34,325
NZ$4,904 per night
includes taxes & fees
Image gallery for Waterfront, Pool & Dock - Spindrift House
1010 out of 10 rating
Exceptional
(27 reviews)
Waterfront, Pool & Dock - Spindrift House
Key West, Florida
8% off
Price is NZ$26,068
NZ$26,068
NZ$3,724 per night
includes taxes & fees
Image gallery for Oceanfront Wellness home w/pool - Mastway House
9.69.6 out of 10 rating
Exceptional
(26 reviews)
Oceanfront Wellness home w/pool - Mastway House
Key West, Florida
8% off
Price is NZ$26,541
NZ$26,541
NZ$3,792 per night
includes taxes & fees
Image gallery for Parking, Pool & Waterfront - Springtide House
9.89.8 out of 10 rating
Exceptional
(42 reviews)
Parking, Pool & Waterfront - Springtide House
Key West, Florida
8% off
Price is NZ$22,712
NZ$22,712
NZ$3,245 per night
includes taxes & fees
Image gallery for Parking, Pet Friendly, Pool & Dock - Aquaria House
9.89.8 out of 10 rating
Exceptional
(37 reviews)
Parking, Pet Friendly, Pool & Dock - Aquaria House
Key West, Florida
8% off
Price is NZ$24,301
NZ$24,301
NZ$3,472 per night
includes taxes & fees
Image gallery for Luxury Home with Heated Pool - The Ebberly Estate
9.09.0 out of 10 rating
Wonderful
(11 reviews)
Luxury Home with Heated Pool - The Ebberly Estate
Key West, Florida
8% off
Price is NZ$30,848
NZ$30,848
NZ$4,407 per night
includes taxes & fees
Image gallery for Waterfront Home, Heated Pool - The Seagate Estate
1010 out of 10 rating
Exceptional
(16 reviews)
Waterfront Home, Heated Pool - The Seagate Estate
Key West, Florida
8% off
Price is NZ$24,073
NZ$24,073
NZ$3,439 per night
includes taxes & fees
Image gallery for 34’ Catamaran Sailboat
9.49.4 out of 10 rating
Exceptional
(35 reviews)
34’ Catamaran Sailboat
Key West, FL
8% off
Price is NZ$3,912
NZ$3,912
NZ$559 per night
includes taxes & fees
Image gallery for TRAVEL THE KEYS OR JUST RELAX AT THE DOCK
9.49.4 out of 10 rating
Exceptional
(28 reviews)
TRAVEL THE KEYS OR JUST RELAX AT THE DOCK
Key West, FL
8% off
Price is NZ$20,240
NZ$20,240
NZ$2,891 per night
includes taxes & fees
Image gallery for Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
1010 out of 10 rating
Exceptional
(35 reviews)
Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
Key West, FL
13% off
Price is NZ$11,195
NZ$11,195
NZ$1,599 per night
includes taxes & fees
Image gallery for Newly Updated! The Grand Cayman Suite
9.29.2 out of 10 rating
Wonderful
(24 reviews)
Newly Updated! The Grand Cayman Suite
Key West, FL
8% off
Price is NZ$9,238
NZ$9,238
NZ$1,320 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$6,907
NZ$6,907
NZ$987 per night
includes taxes & fees
Image gallery for Parking, Pool & Pet Friendly - The Grand Turk
8.48.4 out of 10 rating
Very good
(18 reviews)
Parking, Pool & Pet Friendly - The Grand Turk
Key West, Florida
8% off
Price is NZ$7,421
NZ$7,421
NZ$1,060 per night
includes taxes & fees
Image gallery for Tropical Key West out of the way
9.49.4 out of 10 rating
Exceptional
(172 reviews)
Tropical Key West out of the way
Key West, FL
15% off
Price is NZ$5,596
NZ$5,596
NZ$799 per night
includes taxes & fees
Image gallery for Ocean views! <br>I didn’t do it too
1010 out of 10 rating
Exceptional
(21 reviews)
Ocean views! <br>I didn’t do it too
Key West, FL
7% off
Price is NZ$6,107
NZ$6,107
NZ$872 per night
includes taxes & fees
Image gallery for Penthouse Beach Ocean Views- Live the Dream
9.89.8 out of 10 rating
Exceptional
(243 reviews)
Penthouse Beach Ocean Views- Live the Dream
Key West, FL
12% off
Price is NZ$9,396
NZ$9,396
NZ$1,342 per night
includes taxes & fees
Image gallery for Two Bedroom Residence
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Two Bedroom Residence
Key West, Florida
8% off
Price is NZ$11,904
NZ$11,904
NZ$1,701 per night
includes taxes & fees
Image gallery for Parking, Pool, & Pet Friendly - The Grenada Suite
8.68.6 out of 10 rating
Excellent
(11 reviews)
Parking, Pool, & Pet Friendly - The Grenada Suite
Key West, Florida
8% off
Price is NZ$7,480
NZ$7,480
NZ$1,069 per night
includes taxes & fees
Image gallery for Free Parking, Pool, & Pet Friendly - The Trinidad
9.29.2 out of 10 rating
Wonderful
(35 reviews)
Free Parking, Pool, & Pet Friendly - The Trinidad
Key West, Florida
8% off
Price is NZ$7,002
NZ$7,002
NZ$1,000 per night
includes taxes & fees
Image gallery for Two Bedroom Residence
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Two Bedroom Residence
Key West, Florida
8% off
Price is NZ$11,904
NZ$11,904
NZ$1,701 per night
includes taxes & fees
Image gallery for Two Bedroom Residence
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Two Bedroom Residence
Key West, FL
8% off
Price is NZ$11,904
NZ$11,904
NZ$1,701 per night
includes taxes & fees
Image gallery for Two Bedroom Residence
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Two Bedroom Residence
Key West, Florida
8% off
Price is NZ$11,904
NZ$11,904
NZ$1,701 per night
includes taxes & fees
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Find the best place to stay - Shark Key
Private and Exclusive Beach Getaway
Sleeps 8 · 2 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Florida Keys Beach Getaway
Sleeps 12 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
PET FRIENDLY! SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
213 reviews(213 reviews)
Key West - Stock Island
Sleeps 7 · 2 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront
Sleeps 10 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
52 reviews(52 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
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