Holiday rentals near Key West Express
We found 13,219 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:18 Jul - 25 Jul
Image gallery for Aah!!! Poppy's Paradise

1010 out of 10 rating
Exceptional
(39 reviews)
Aah!!! Poppy's Paradise
Captiva, FL
7% off
Price is NZ$12,525
NZ$12,525
NZ$1,789 per night
includes taxes & fees
Image gallery for CASA CORAL☀️Heated Pool 🐠Canal🚣♀️Games🎱Golf⛳️ Family🛏 🌞Kayak

9.69.6 out of 10 rating
Exceptional
(7 reviews)
CASA CORAL☀️Heated Pool 🐠Canal🚣♀️Games🎱Golf⛳️ Family🛏 🌞Kayak
Cape Coral, FL
8% off
Price is NZ$5,062
NZ$5,062
NZ$723 per night
includes taxes & fees
Image gallery for The Hyde Away-Beautiful newer home exquisitely decorated on a fresh water canal.

1010 out of 10 rating
Exceptional
(16 reviews)
The Hyde Away-Beautiful newer home exquisitely decorated on a fresh water canal.
Cape Coral, FL
7% off
Price is NZ$4,235
NZ$4,235
NZ$605 per night
includes taxes & fees
Image gallery for Pet friendly spacious home for large groups! Heated pool & jacuzzi, games!

9.49.4 out of 10 rating
Exceptional
(13 reviews)
Pet friendly spacious home for large groups! Heated pool & jacuzzi, games!
Cape Coral, FL
13% off
Price is NZ$8,571
NZ$8,571
NZ$1,224 per night
includes taxes & fees
Image gallery for Pool home, 4 bedroom/ 3bath in a great location in Cape Coral!

9.89.8 out of 10 rating
Exceptional
(74 reviews)
Pool home, 4 bedroom/ 3bath in a great location in Cape Coral!
Cape Coral, FL
7% off
Price is NZ$2,665
NZ$2,665
NZ$381 per night
includes taxes & fees
Image gallery for 2 Blocks To Beach, Large Private Pool, 4 bedroom home with 2 separate suites

9.49.4 out of 10 rating
Exceptional
(28 reviews)
2 Blocks To Beach, Large Private Pool, 4 bedroom home with 2 separate suites
Fort Myers Beach, FL
8% off
Price is NZ$5,361
NZ$5,361
NZ$766 per night
includes taxes & fees
Image gallery for Waterfront Pink House with Private Dock & Pool!

9.89.8 out of 10 rating
Exceptional
(58 reviews)
Waterfront Pink House with Private Dock & Pool!
Captiva, FL
10% off
Price is NZ$14,517
NZ$14,517
NZ$2,074 per night
includes taxes & fees
Image gallery for New Stilt Home: Heated Pool, Near Beach & Times Sq

1010 out of 10 rating
Exceptional
(13 reviews)
New Stilt Home: Heated Pool, Near Beach & Times Sq
Fort Myers Beach, FL
6% off
Price is NZ$5,134
NZ$5,134
NZ$733 per night
includes taxes & fees
Image gallery for 5BR/6.5BA LUXURY 5.5M WATERFRONT home w/ Amazing Views INCLUDES OWNER'S SUITE!

1010 out of 10 rating
Exceptional
(44 reviews)
5BR/6.5BA LUXURY 5.5M WATERFRONT home w/ Amazing Views INCLUDES OWNER'S SUITE!
Bonita Springs, FL
5% off
Price is NZ$13,684
NZ$13,684
NZ$1,955 per night
includes taxes & fees
Image gallery for Brand New Luxury Pool & Spa Home Near Beach!

9.89.8 out of 10 rating
Exceptional
(16 reviews)
Brand New Luxury Pool & Spa Home Near Beach!
Naples, FL
8% off
Price is NZ$6,379
NZ$6,379
NZ$911 per night
includes taxes & fees
Image gallery for Canal Waterfront Serenity Retreat

9.89.8 out of 10 rating
Exceptional
(8 reviews)
Canal Waterfront Serenity Retreat
Cape Coral, Florida
6% off
Price is NZ$2,040
NZ$2,040
NZ$291 per night
includes taxes & fees
Image gallery for Florida Canal Balcony view- Quiet Neighborhood and 10 minutes to the Beach!

9.29.2 out of 10 rating
Wonderful
(21 reviews)
Florida Canal Balcony view- Quiet Neighborhood and 10 minutes to the Beach!
Bonita Springs, FL
7% off
Price is NZ$2,125
NZ$2,125
NZ$304 per night
includes taxes & fees
Image gallery for Spring Summer specials- heated pool, close to many stores and restaurants

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Spring Summer specials- heated pool, close to many stores and restaurants
Cape Coral, FL
8% off
Price is NZ$3,562
NZ$3,562
NZ$509 per night
includes taxes & fees
Image gallery for Our condo will be ready and updated by Nov 1st, 2023 - Great Rates and Amenities

9.69.6 out of 10 rating
Exceptional
(140 reviews)
Our condo will be ready and updated by Nov 1st, 2023 - Great Rates and Amenities
Sanibel, FL
8% off
Price is NZ$3,980
NZ$3,980
NZ$569 per night
includes taxes & fees
Image gallery for BONITA BEACHFAMILY MANSION 4 BED3.5BATH CUSTOM NEW POOL OUTDOOR KITCHEN BBQ

9.49.4 out of 10 rating
Exceptional
(62 reviews)
BONITA BEACHFAMILY MANSION 4 BED3.5BATH CUSTOM NEW POOL OUTDOOR KITCHEN BBQ
Bonita Springs, FL
7% off
Price is NZ$5,761
NZ$5,761
NZ$823 per night
includes taxes & fees
Image gallery for Ultra Modern Photogenic POOL home with pergola, astroturf, fire pit & Movie RM

9.89.8 out of 10 rating
Exceptional
(18 reviews)
Ultra Modern Photogenic POOL home with pergola, astroturf, fire pit & Movie RM
Cape Coral, FL
8% off
Price is NZ$4,563
NZ$4,563
NZ$652 per night
includes taxes & fees
Image gallery for Naples Vanderbilt Beach Getaway

9.49.4 out of 10 rating
Exceptional
(9 reviews)
Naples Vanderbilt Beach Getaway
Naples, FL
8% off
Price is NZ$4,253
NZ$4,253
NZ$608 per night
includes taxes & fees
Image gallery for New! Feelin' Bonita - Approx 2 Miles to the Beach! Heated Pool!

1010 out of 10 rating
Exceptional
(11 reviews)
New! Feelin' Bonita - Approx 2 Miles to the Beach! Heated Pool!
Bonita Springs, FL
17% off
Price is NZ$4,625
NZ$4,625
NZ$661 per night
includes taxes & fees
Image gallery for Blue Diamond Beach Home

1010 out of 10 rating
Exceptional
(16 reviews)
Blue Diamond Beach Home
Bonita Springs, FL
8% off
Price is NZ$16,171
NZ$16,171
NZ$2,310 per night
includes taxes & fees
Image gallery for Waterfront House with Heated Pool, Jacuzzi & Private Dock

1010 out of 10 rating
Exceptional
(11 reviews)
Waterfront House with Heated Pool, Jacuzzi & Private Dock
Fort Myers, FL
12% off
Price is NZ$8,671
NZ$8,671
NZ$1,239 per night
includes taxes & fees
Image gallery for The "Tommy Suite". North end of the Island! 400 yrds. to The Gulf of Mexico!

9.69.6 out of 10 rating
Exceptional
(16 reviews)
The "Tommy Suite". North end of the Island! 400 yrds. to The Gulf of Mexico!
Fort Myers Beach, FL
7% off
Price is NZ$2,567
NZ$2,567
NZ$367 per night
includes taxes & fees
Image gallery for Great Reviews, Family Friendly, Sunny Sanibel

1010 out of 10 rating
Exceptional
(95 reviews)
Great Reviews, Family Friendly, Sunny Sanibel
Sanibel, FL
8% off
Price is NZ$4,882
NZ$4,882
NZ$697 per night
includes taxes & fees
Image gallery for HEATED SALTWATER POOL, HOT TUB 4-beds 3-baths, Gulf access boat lift, VERY CLEAN

1010 out of 10 rating
Exceptional
(15 reviews)
HEATED SALTWATER POOL, HOT TUB 4-beds 3-baths, Gulf access boat lift, VERY CLEAN
Cape Coral, FL
7% off
Price is NZ$4,903
NZ$4,903
NZ$700 per night
includes taxes & fees
Image gallery for Alluring Cape Coral Home with Pool, Lanai, & Dock with gulf access!

9.89.8 out of 10 rating
Exceptional
(53 reviews)
Alluring Cape Coral Home with Pool, Lanai, & Dock with gulf access!
Cape Coral, FL
7% off
Price is NZ$2,766
NZ$2,766
NZ$395 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
1,304 reviews(1,304 reviews)
NEW REMODEL Steps from private beach access! 4 BR Family Friendly CLEAN
Sleeps 11 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Casa Playa #605 - Beach Bungalow
Sleeps 2 · 1 bedroom · 1 bathroom
7.07.0 out of 10
Goodgood
2 reviews(2 reviews)
Charming 2-bedroom condo with AC and WiFi in wonderful Fort Myers, FL
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Hidden Secret Waterfront Retreat
Sleeps 9 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
1 Bed / 1 Bath, studio
Sleeps 2 · 1 bedroom · 1 bathroom
2.02.0 out of 10
2 reviews(2 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