Condo
10.0(219 Reviews)
2 Bedrooms
4 Guests
Oceanfront
Parking
Pool
Ocean View
US $430/Night
7 Nights - US $3,012
Key West Holiday Rentals
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Compare Villas, Resorts, & Rentals in Key West
10.0
US $953/Night
7 Nights - US $6,673
House
10.0(5 Reviews)
1 Bedroom
Child Friendly
US $421/Night
7 Nights - US $2,947
Condo
10.0(194 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $305/Night
7 Nights - US $2,134
House
10.0(4 Reviews)
1 Bedroom
3 Guests
View
Pet Friendly- Child Friendly
Security/Safety
US $364/Night
7 Nights - US $2,548
House
10.0(193 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $746/Night
7 Nights - US $5,221
House
10.0(189 Reviews)
2 Bedrooms
6 Guests
Private Pool- Pool
Balcony/Terrace
Kitchen
US $872/Night
7 Nights - US $6,106
Condo
10.0(178 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $197/Night
7 Nights - US $1,380
Condo
10.0(173 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
Hot Tub- Parking
- Pool
US $587/Night
7 Nights - US $4,110
Luxury Holiday Rentals in Key West
Over 4891+ Luxury Holiday Rentals in or Near Key West
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Boat Rental
4 Bedrooms
6 Guests
- Parking
- Kitchen
Air Conditioner
Internet
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New
House
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
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New
Boat Rental
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
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Boat Rental
6 Bedrooms
12 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $7,602/Night
7 Nights - US $53,214
Top-Rated Holiday Rentals with a Pool in Key West
Over 3500+ The Best Private Villas and Holiday Rentals in Key West with a Pool
House
10.0(251 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $576/Night
7 Nights - US $4,029
House
10.0(218 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $576/Night
7 Nights - US $4,029
Cottage
10.0(209 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $229/Night
7 Nights - US $1,602
House
10.0(199 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,040/Night
7 Nights - US $7,279
House
10.0(182 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $1,029/Night
7 Nights - US $7,201
Condo
10.0(169 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $314/Night
7 Nights - US $2,199
Condo
10.0(164 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $465/Night
7 Nights - US $3,256
Condo
10.0(154 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $547/Night
7 Nights - US $3,829
House
10.0(153 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Oceanfront
Breakfast- Parking
US $1,568/Night
7 Nights - US $10,976
Pet-Friendly Holiday Rentals in Key West
Over 1542+ Pet-Friendly Holiday Rentals in or Near Key West
Apartment
10.0(99 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $332/Night
7 Nights - US $2,327
US $1,339/Night
7 Nights - US $9,373
Apartment
10.0(1 Review)
1 Bedroom
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $787/Night
7 Nights - US $5,511
Condo
10.0(76 Reviews)
1 Bedroom
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $431/Night
7 Nights - US $3,018
House
10.0(2 Reviews)
6 Bedrooms
16 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,896/Night
7 Nights - US $13,269
Condo
10.0(69 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $744/Night
7 Nights - US $5,205
House
10.0(42 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $672/Night
7 Nights - US $4,707
House
10.0(40 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,321/Night
7 Nights - US $9,246
Condo
10.0(37 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $400/Night
7 Nights - US $2,802
Large Holiday Rentals and Private Villas in Key West
Over 537+ Large Holiday Rentals and Private Villas in or Near Key West
Villa
10.0(64 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $760/Night
7 Nights - US $5,319
House
10.0(3 Reviews)
4 Bedrooms
12 Guests
- Internet
- Child Friendly
- Laundry
- Security/Safety
US $2,492/Night
7 Nights - US $17,441
Villa
7.4(3 Reviews)
1 Bedroom
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $421/Night
7 Nights - US $2,947
Villa
10.0(25 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $312/Night
7 Nights - US $2,185
House
10.0(2 Reviews)
6 Bedrooms
14 Guests
- Parking
- Pool
- View
- Air Conditioner
US $1,413/Night
7 Nights - US $9,894
Villa
10.0(22 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
US $503/Night
7 Nights - US $3,520
Villa
10.0(10 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
US $506/Night
7 Nights - US $3,541
Villa
10.0(3 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
US $367/Night
7 Nights - US $2,570
House
10.0(2 Reviews)
2 Bedrooms
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,610/Night
7 Nights - US $11,268
Wheelchair Accessible Holiday Homes in Key West
Over 1084+ Wheelchair Accessible Holiday Homes in or Near Key West
Condo
10.0(152 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $587/Night
7 Nights - US $4,109
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Pool
- Balcony/Terrace
- View
- Air Conditioner
US $474/Night
7 Nights - US $3,318
US $2,792/Night
7 Nights - US $19,544
Condo
10.0(129 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $570/Night
7 Nights - US $3,992
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- View
- Air Conditioner
US $276/Night
7 Nights - US $1,932
Condo
10.0(74 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $345/Night
7 Nights - US $2,418
US $703/Night
7 Nights - US $4,918
Condo
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
Spa
US $633/Night
7 Nights - US $4,430
Condo
10.0(33 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $568/Night
7 Nights - US $3,974
Key West Private Villas and Holiday Homes Under $200
Over 295+ Key West Private Villas and Holiday Homes Under $200
Apartment
10.0(28 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $141/Night
7 Nights - US $987
US $190/Night
7 Nights - US $1,330
Bed & Breakfast
9.8(191 Reviews)
1 Bedroom
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $186/Night
7 Nights - US $1,304
House
10.0(12 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $163/Night
7 Nights - US $1,140
Bed & Breakfast
9.0(1414 Reviews)
11 Bedrooms
18 Guests
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $199/Night
7 Nights - US $1,393
House
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $191/Night
7 Nights - US $1,339
House
10.0(11 Reviews)
1 Bedroom
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $174/Night
7 Nights - US $1,219
House
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $195/Night
7 Nights - US $1,368
US $174/Night
7 Nights - US $1,221
Instantly Bookable Holiday Homes in Key West
Over 3175+ Instantly Bookable Holiday Homes in or Near Key West
Cottage
10.0(169 Reviews)
2 Bedrooms
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $431/Night
7 Nights - US $3,017
House
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $261/Night
7 Nights - US $1,826
House
10.0(135 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $787/Night
7 Nights - US $5,508
Condo
10.0(126 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $257/Night
7 Nights - US $1,801
House
10.0(111 Reviews)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $341/Night
7 Nights - US $2,384
Condo
10.0(108 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $379/Night
7 Nights - US $2,653
House
10.0(107 Reviews)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $327/Night
7 Nights - US $2,291
House
10.0(104 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $466/Night
7 Nights - US $3,264
Apartment
10.0(92 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $693/Night
7 Nights - US $4,850
Book a Last Minute Place to Stay in Key West
About Casai's Private Villas and Holiday Rentals in Key West
Discover more than 4900 vacation rentals available in Key West. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Key West.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Key West, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Key West. On average, places to stay near Key West offer 749.58 ft², with nightly prices averaging US $753.
With Casai, finding and comparing holiday rentals in Key West is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Key West, FL
There are 4900 Key West, FL Holiday Rentals
- Prices for a holiday home in Key West start at US $111
- Top rated vacation home in Key West is Almond Tree Inn Hotel - Adults Only
- Most popular short term in Key West is Blue Marlin Motel
- Cheapest place to stay in Key West is Tranquil condo/AC, WIFI, Outdoor Pool, Full kitchen, Livingroom in Key West
- Most expensive holiday rental in Key West is Beachfront Key West + Free Breakfast, Bar & Pool
Recently Booked Holiday Rentals in Key West
Frequently Asked Questions About Key West?
What are the top holiday rentals in Key West?
With numerous options available in Key West, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Key West:
- Almond Tree Inn Hotel - Adults Only
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Walkable Cottage w/Pool Access in Key West!
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- Everything Key West has to offer @ Mango Cottage
- ~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
How many holiday rentals have private pools in Key West?
Discover a selection of holiday rentals with private pools near Key West with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Key West are best for families?
If you're searching for a family-friendly holiday home in Key West, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Key West:
How many Casai.com holiday rentals are available in Key West?
As of 2026, Casai boasts over 4900 properties listed in the Key West area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Key West.
Nearby Neighborhood (15)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2107 |
| Old Town Vacation Rentals in Key West, Florida | 2025 |
| Downtown Vacation Rentals in Key West, Florida | 850 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 714 |
| Historic Seaport Vacation Rentals in Key West, Florida | 319 |
| Truman Annex Vacation Rentals in Key West, Florida | 237 |
| Meadows Vacation Rentals in Key West, Florida | 104 |
| The Meadows Vacation Rentals in Key West, Florida | 104 |
| New Town Vacation Rentals in Key West, Florida | 97 |
| Bahama Village Vacation Rentals in Key West, Florida | 62 |
| Midtown Vacation Rentals in Key West, Florida | 40 |
| White St. Gallery Vacation Rentals in Key West, Florida | 4477 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4473 |
| Sunset Key Vacation Rentals in Key West, Florida | 3658 |
| Geiger Key Vacation Rentals in Key West, Florida | 53 |
