Holiday rentals near Key West Express
We found 13,902 holiday rentals — enter your dates for availability
If you'd like to stay close to Key West Express, take a look at private holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. At the end of the day, you're sure to 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 - Key West Express
Showing deals for:7 Nov - 14 Nov
Image gallery for RELAX and Unwind on Fort Myers Beach in a 2BR/2BA Gorgeous Gulf views and Pool
9.89.8 out of 10 rating
Exceptional
(64 reviews)
RELAX and Unwind on Fort Myers Beach in a 2BR/2BA Gorgeous Gulf views and Pool
Fort Myers Beach, FL
8% off
Price is AU$3,208
AU$3,208
AU$458 per night
includes taxes & fees
Image gallery for Toes In the Sand: 3Br/2BA with Pool,Bikes&Games- 4 min walk to Beach & Publix!
9.89.8 out of 10 rating
Exceptional
(108 reviews)
Toes In the Sand: 3Br/2BA with Pool,Bikes&Games- 4 min walk to Beach & Publix!
Fort Myers Beach, FL
8% off
Price is AU$4,627
AU$4,627
AU$661 per night
includes taxes & fees
Image gallery for Steps from Bonita Beach! Great family home with a pool on salt water canal!
9.69.6 out of 10 rating
Exceptional
(46 reviews)
Steps from Bonita Beach! Great family home with a pool on salt water canal!
Bonita Springs, FL
8% off
Price is AU$6,396
AU$6,396
AU$914 per night
includes taxes & fees
Image gallery for Waterfront House with Heated Pool, Jacuzzi & Private Dock
1010 out of 10 rating
Exceptional
(12 reviews)
Waterfront House with Heated Pool, Jacuzzi & Private Dock
Fort Myers, FL
16% off
Price is AU$7,427
AU$7,427
AU$1,061 per night
includes taxes & fees
Image gallery for Cape Heaven, heated pool, and volleyball court, and park.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Cape Heaven, heated pool, and volleyball court, and park.
Cape Coral, FL
8% off
Price is AU$3,689
AU$3,689
AU$527 per night
includes taxes & fees
Image gallery for DIRECT SAIL BOATS -GULF Access 5 bedroom 3 bath , Villa stunning View, sleep 11
9.29.2 out of 10 rating
Wonderful
(64 reviews)
DIRECT SAIL BOATS -GULF Access 5 bedroom 3 bath , Villa stunning View, sleep 11
Cape Coral, FL
5% off
Price is AU$4,023
AU$4,023
AU$575 per night
includes taxes & fees
Image gallery for OCEANFRONT RETREAT/Monthly rental
9.89.8 out of 10 rating
Exceptional
(6 reviews)
OCEANFRONT RETREAT/Monthly rental
Bonita Springs, FL
7% off
Price is AU$3,406
AU$3,406
AU$487 per night
includes taxes & fees
Image gallery for Prettiest Home & Best value in the area!!!!
9.89.8 out of 10 rating
Exceptional
(59 reviews)
Prettiest Home & Best value in the area!!!!
Cape Coral, FL
14% off
Price is AU$3,178
AU$3,178
AU$454 per night
includes taxes & fees
Image gallery for Cape Villa Family Friendly Canal front 4 Bedroom Southern Facing Heated Pool Spa
1010 out of 10 rating
Exceptional
(29 reviews)
Cape Villa Family Friendly Canal front 4 Bedroom Southern Facing Heated Pool Spa
Cape Coral, FL
8% off
Price is AU$4,948
AU$4,948
AU$707 per night
includes taxes & fees
Image gallery for Cozy and warm 3-bedroom cottage with a pool in the island
8.28.2 out of 10 rating
Very good
(11 reviews)
Cozy and warm 3-bedroom cottage with a pool in the island
Saint James City, FL
7% off
Price is AU$2,449
AU$2,449
AU$350 per night
includes taxes & fees
Image gallery for Boater's dream! Waterfront, pool large dock, tiki hut, hot tub and sauna.
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Boater's dream! Waterfront, pool large dock, tiki hut, hot tub and sauna.
Cape Coral, FL
6% off
Price is AU$5,842
AU$5,842
AU$835 per night
includes taxes & fees
Image gallery for NEW Aqua Vista-SW Cape Coral Gulf Access Pool Home
1010 out of 10 rating
Exceptional
(23 reviews)
NEW Aqua Vista-SW Cape Coral Gulf Access Pool Home
Cape Coral, FL
7% off
Price is AU$3,700
AU$3,700
AU$529 per night
includes taxes & fees
Image gallery for Luxury waterfront with heated- saltwater pool
9.29.2 out of 10 rating
Wonderful
(16 reviews)
Luxury waterfront with heated- saltwater pool
Cape Coral, FL
7% off
Price is AU$2,750
AU$2,750
AU$393 per night
includes taxes & fees
Image gallery for Waterfront Cottage! Kayaking, birdwatching, fishing in quiet bay access setting
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Waterfront Cottage! Kayaking, birdwatching, fishing in quiet bay access setting
Bonita Springs, FL
7% off
Price is AU$2,773
AU$2,773
AU$396 per night
includes taxes & fees
Image gallery for Enjoy your private resort/villa on the water with incredible views and location!
9.89.8 out of 10 rating
Exceptional
(70 reviews)
Enjoy your private resort/villa on the water with incredible views and location!
Cape Coral, FL
8% off
Price is AU$15,399
AU$15,399
AU$2,200 per night
includes taxes & fees
Image gallery for Sunrise Haven: Your Retreat in Bonita Springs 6 bedrooms/5 bath, close to Gulf
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Sunrise Haven: Your Retreat in Bonita Springs 6 bedrooms/5 bath, close to Gulf
Bonita Springs, FL
8% off
Price is AU$7,509
AU$7,509
AU$1,073 per night
includes taxes & fees
Image gallery for Santa Maria Resort- Great Resort and Condo!! Large refurbished pool & hot tub!
8.08.0 out of 10 rating
Very good
(5 reviews)
Santa Maria Resort- Great Resort and Condo!! Large refurbished pool & hot tub!
Fort Myers Beach, FL
15% off
Price is AU$2,905
AU$2,905
AU$415 per night
includes taxes & fees
Image gallery for Waterfront Oasis in SW Cape Coral Florida
1010 out of 10 rating
Exceptional
(10 reviews)
Waterfront Oasis in SW Cape Coral Florida
Cape Coral, FL
11% off
Price is AU$2,537
AU$2,537
AU$362 per night
includes taxes & fees
Image gallery for Sanctuary w/covered heated saltwater pool on canal
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Sanctuary w/covered heated saltwater pool on canal
Cape Coral, FL
7% off
Price is AU$2,163
AU$2,163
AU$309 per night
includes taxes & fees
Image gallery for 109 Charming Coastal Haven: Heated Pool, Walk to Beach
9.49.4 out of 10 rating
Exceptional
(9 reviews)
109 Charming Coastal Haven: Heated Pool, Walk to Beach
Fort Myers Beach, FL
6% off
Price is AU$4,384
AU$4,384
AU$626 per night
includes taxes & fees
Image gallery for Dream catcher, where your dreams come true! Beachy waterfront Villa Heated pool
1010 out of 10 rating
Exceptional
(48 reviews)
Dream catcher, where your dreams come true! Beachy waterfront Villa Heated pool
Cape Coral, FL
11% off
Price is AU$3,295
AU$3,295
AU$471 per night
includes taxes & fees
Image gallery for Beautiful Villa Lake View! Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!
1010 out of 10 rating
Exceptional
(205 reviews)
Beautiful Villa Lake View! Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!
Cape Coral, FL
16% off
Price is AU$3,749
AU$3,749
AU$536 per night
includes taxes & fees
Image gallery for Canalfront/Outdoor Kitchen/Pool/Spa/Boat Dock
1010 out of 10 rating
Exceptional
(34 reviews)
Canalfront/Outdoor Kitchen/Pool/Spa/Boat Dock
Cape Coral, FL
7% off
Price is AU$3,113
AU$3,113
AU$445 per night
includes taxes & fees
Image gallery for Ocean View Condominium
9.69.6 out of 10 rating
Exceptional
(31 reviews)
Ocean View Condominium
Fort Myers Beach, FL
8% off
Price is AU$2,423
AU$2,423
AU$346 per night
includes taxes & fees
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Find the best place to stay - Key West Express
Edison Beach House
Sleeps 4 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
1,448 reviews(1,448 reviews)
Steps to BEACH/POOL/Downtown
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
Seashell Suites 2 - Steps to the Beach, Outdoor Shower, & More!
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
CASA BELLA" B" - 1 Bed/1 Bath STEPS TO THE BEACH - Sleeps 2
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Beautiful 1-bedroom condo with the best views ocean,back bay & beautiful sunset
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Studio Cottage/Short Walk to Beach
Sleeps 2 · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
32 reviews(32 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