Weston Hills Holiday Rentals
Apartment
- Orlando
- ·
- Sunrise Lakes
- 0.12 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
Parking
Pool
Ocean View
View
US $93/Night
7 Nights - US $648
House
Affordable Luxury Home Near Walt Disney World - Sunshine Villa at Glenbrook Resort, Orlando, Florida
- Orlando
- ·
- Four Corners
- 3.29 mi to center
10.0Exceptional
(13 Reviews)
4 Bedrooms
4 Baths
8 Guests
1948.27 ft²
Oceanfront
Hot Tub
Breakfast- Parking
US $129/Night
7 Nights - US $903
Villa
- Orlando
- ·
- Four Corners
- 2.63 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Pool
Kitchen
Air Conditioner
Internet
US $345/Night
7 Nights - US $2,418
Apartment
- Orlando
- ·
- Clear Creek
- 0.01 mi to center
9.8Exceptional
(28 Reviews)
1 Bedroom
1 Bath
5 Guests
- Parking
Balcony/Terrace- Kitchen
- Air Conditioner
US $85/Night
7 Nights - US $595
House
- Orlando
- ·
- Clear Creek
- 0.42 mi to center
10.0Exceptional
(10 Reviews)
5 Bedrooms
3 Baths
12 Guests
2002.09 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $718/Night
7 Nights - US $5,023
House
- Orlando
- ·
- Four Corners
- 3.34 mi to center
9.8Exceptional
(6 Reviews)
1 Bedroom
3 Baths
10 Guests
1963 ft²
Private Pool- Parking
- Pool
- Kitchen
US $223/Night
7 Nights - US $1,563
Cottage
- Orlando
- ·
- Four Corners
- 3.99 mi to center
9.4Exceptional
(8 Reviews)
1 Bedroom
1 Bath
6 Guests
850 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $126/Night
7 Nights - US $879
Villa
- Orlando
- ·
- Four Corners
- 2.34 mi to center
9.2Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1432 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $266/Night
7 Nights - US $1,859
New
House
- Orlando
- ·
- Silver Creek
- 0.10 mi to center
1 Bedroom
3 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $563/Night
7 Nights - US $3,941
Luxury Holiday Rentals in Weston Hills
Over 2679+ Luxury Holiday Rentals in or Near Weston Hills
House
- Orlando
- ·
- Four Corners
- 3.07 mi to center
10 Bedrooms
8 Baths
29 Guests
4499.31 ft²
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
US $1,768/Night
7 Nights - US $12,379
House
- Orlando
- ·
- Four Corners
- 2.98 mi to center
10 Bedrooms
8 Baths
28 Guests
43421.61 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $1,708/Night
7 Nights - US $11,956
Villa
- Orlando
- ·
- Four Corners
- 3.19 mi to center
10 Bedrooms
8 Baths
22 Guests
- Parking
- Pool
Spa- Balcony/Terrace
US $1,699/Night
7 Nights - US $11,896
House
- Orlando
- ·
- Four Corners
- 3.28 mi to center
5 Bedrooms
5 Baths
12 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $1,583/Night
7 Nights - US $11,082
House
- Orlando
- ·
- Four Corners
- 3.44 mi to center
10 Bedrooms
8 Baths
21 Guests
3003.13 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,389/Night
7 Nights - US $9,724
Villa
- Orlando
- ·
- Four Corners
- 3.48 mi to center
10 Bedrooms
8 Baths
26 Guests
4951.4 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,243/Night
7 Nights - US $8,703
Villa
- Orlando
- ·
- Four Corners
- 3.43 mi to center
9.6Exceptional
(26 Reviews)
8 Bedrooms
6 Baths
23 Guests
4025 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,242/Night
7 Nights - US $8,695
House
- Orlando
- ·
- Four Corners
- 2.72 mi to center
10 Bedrooms
8 Baths
24 Guests
2604.87 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,200/Night
7 Nights - US $8,402
House
- Orlando
- ·
- Four Corners
- 2.07 mi to center
8.4Excellent
(6 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,192/Night
7 Nights - US $8,345
Top-Rated Holiday Rentals with a Pool in Weston Hills
Over 2403+ The Best Private Villas and Holiday Rentals in Weston Hills with a Pool
Villa
- Orlando
- ·
- Orange Tree
- 0.39 mi to center
10.0Exceptional
(265 Reviews)
4 Bedrooms
3 Baths
10 Guests
2500 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $356/Night
7 Nights - US $2,491
House
- Orlando
- ·
- Four Corners
- 2.20 mi to center
10.0Exceptional
(211 Reviews)
5 Bedrooms
3 Baths
10 Guests
2928 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $283/Night
7 Nights - US $1,980
Villa
- Orlando
- ·
- Mission Park
- 0.12 mi to center
10.0Exceptional
(130 Reviews)
4 Bedrooms
3 Baths
8 Guests
1740 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $267/Night
7 Nights - US $1,868
Villa
- Orlando
- ·
- Orange Tree
- 0.27 mi to center
10.0Exceptional
(112 Reviews)
6 Bedrooms
3 Baths
12 Guests
3105 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $372/Night
7 Nights - US $2,607
House
- Orlando
- ·
- Orange Tree
- 0.27 mi to center
10.0Exceptional
(92 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $332/Night
7 Nights - US $2,326
House
- Orlando
- ·
- Clear Creek
- 0.36 mi to center
10.0Exceptional
(76 Reviews)
3 Bedrooms
3 Baths
4 Guests
1502 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $221/Night
7 Nights - US $1,550
Resort
- Orlando
- ·
- West Kissimmee
- 3.05 mi to center
10.0Exceptional
(76 Reviews)
1 Bath
4 Guests
781 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $113/Night
7 Nights - US $788
House
- Orlando
- ·
- Orange Tree
- 0.18 mi to center
10.0Exceptional
(74 Reviews)
5 Bedrooms
4 Baths
10 Guests
2201 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $312/Night
7 Nights - US $2,182
Villa
- Orlando
- ·
- Four Corners
- 3.37 mi to center
10.0Exceptional
(73 Reviews)
4 Bedrooms
2 Baths
10 Guests
20451 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $325/Night
7 Nights - US $2,277
Pet-Friendly Holiday Rentals in Weston Hills
Over 361+ Pet-Friendly Holiday Rentals in or Near Weston Hills
House
- Orlando
- ·
- Weston Hills
- 0.20 mi to center
1 Bedroom
1 Bath
8 Guests
1895 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $392/Night
7 Nights - US $2,741
Villa
- Orlando
- ·
- Weston Hills
- 0.05 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
9 Guests
10763.91 ft²
- Parking
Pet Friendly
Child Friendly
Security/Safety
US $200/Night
7 Nights - US $1,400
US $533/Night
7 Nights - US $3,729
House
- Orlando
- ·
- Four Corners
- 2.79 mi to center
9.6Exceptional
(166 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $178/Night
7 Nights - US $1,246
House
- Orlando
- ·
- Four Corners
- 3.17 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
6 Baths
12 Guests
3121.53 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $490/Night
7 Nights - US $3,430
New
House
- Orlando
- ·
- Silver Creek
- 0.10 mi to center
8.4Excellent
(78 Reviews)
10 Bedrooms
6 Baths
24 Guests
1878 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $211/Night
7 Nights - US $1,479
New
House
- Orlando
- ·
- Four Corners
- 3.39 mi to center
8.0Excellent
(80 Reviews)
4 Bedrooms
3 Baths
10 Guests
2000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $204/Night
7 Nights - US $1,427
New
House
- Orlando
- ·
- Four Corners
- 3.10 mi to center
7.0Very Good
(37 Reviews)
4 Bedrooms
2 Baths
8 Guests
1600 ft²
- Private Pool
- Parking
- Pool
- Kitchen
US $192/Night
7 Nights - US $1,343
House
- Orlando
- ·
- Four Corners
- 3.26 mi to center
6 Bedrooms
4 Baths
14 Guests
2928 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $570/Night
7 Nights - US $3,989
Large Holiday Rentals and Private Villas in Weston Hills
Over 1727+ Large Holiday Rentals and Private Villas in or Near Weston Hills
Villa
- Orlando
- ·
- Four Corners
- 3.26 mi to center
2 Bedrooms
1 Bath
14 Guests
3200 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $418/Night
7 Nights - US $2,928
House
- Orlando
- ·
- Four Corners
- 3.20 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
8 Baths
28 Guests
4380.91 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $971/Night
7 Nights - US $6,795
Villa
- Orlando
- ·
- Four Corners
- 2.70 mi to center
1 Bedroom
1 Bath
- Pool
- Kitchen
- Air Conditioner
- Internet
US $362/Night
7 Nights - US $2,533
Villa
- Orlando
- ·
- Four Corners
- 2.46 mi to center
1 Bedroom
3 Baths
8 Guests
2045 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $256/Night
7 Nights - US $1,795
House
- Orlando
- ·
- Four Corners
- 3.14 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
4 Baths
10 Guests
2271.19 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $439/Night
7 Nights - US $3,075
New
House
- Orlando
- ·
- Four Corners
- 3.10 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
5 Baths
10 Guests
1800 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $350/Night
7 Nights - US $2,450
New
Villa
- Orlando
- ·
- Orange Tree
- 0.29 mi to center
9.8Exceptional
(43 Reviews)
4 Bedrooms
3 Baths
8 Guests
2100 ft²
- Parking
- Pool
- Ocean View
- View
US $286/Night
7 Nights - US $2,001
New
House
- Orlando
- ·
- Four Corners
- 3.28 mi to center
9.6Exceptional
(5 Reviews)
5 Bedrooms
4 Baths
14 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $275/Night
7 Nights - US $1,928
Villa
- Orlando
- ·
- Four Corners
- 3.09 mi to center
6.0Good
(1 Review)
10 Bedrooms
8 Baths
26 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $864/Night
7 Nights - US $6,049
Wheelchair Accessible Holiday Homes in Weston Hills
Over 41+ Wheelchair Accessible Holiday Homes in or Near Weston Hills
Resort
- Orlando
- ·
- West Kissimmee
- 3.00 mi to center
10.0Exceptional
(31 Reviews)
1 Bath
4 Guests
781 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $113/Night
7 Nights - US $788
House
- Orlando
- ·
- Four Corners
- 1.91 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
1657.64 ft²
- Parking
- Pool
- Internet
- Child Friendly
US $140/Night
7 Nights - US $980
House
- Orlando
- ·
- Four Corners
- 2.66 mi to center
8.6Fabulous
(29 Reviews)
1 Bedroom
1 Bath
- Pool
- Internet
- Child Friendly
Wheelchair Accessible
US $187/Night
7 Nights - US $1,309
House
- Orlando
- ·
- Four Corners
- 3.37 mi to center
9 Bedrooms
8 Baths
28 Guests
4300 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,109/Night
7 Nights - US $7,761
House
- Orlando
- ·
- Orange Tree
- 0.11 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
2271.19 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $344/Night
7 Nights - US $2,405
Condo
- Orlando
- ·
- Four Corners
- 1.82 mi to center
9.4Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $272/Night
7 Nights - US $1,904
Condo
- Orlando
- ·
- Four Corners
- 1.93 mi to center
9.4Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $262/Night
7 Nights - US $1,834
Condo
- Orlando
- ·
- Four Corners
- 1.82 mi to center
9.6Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $342/Night
7 Nights - US $2,394
House
- Orlando
- ·
- Four Corners
- 2.44 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
9 Guests
1888 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $123/Night
7 Nights - US $861
Weston Hills Private Villas and Holiday Homes Under $200
Over 537+ Weston Hills Private Villas and Holiday Homes Under $200
US $88/Night
7 Nights - US $618
Villa
- Orlando
- ·
- Orange Tree
- 0.08 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
1851.39 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $198/Night
7 Nights - US $1,386
Cottage
- Orlando
- ·
- Orange Tree
- 0.17 mi to center
1 Bedroom
1 Bath
- Parking
- Pool
- Kitchen
- Air Conditioner
US $191/Night
7 Nights - US $1,337
New
House
- Orlando
- ·
- Weston Hills
- 0.18 mi to center
4 Bedrooms
2 Baths
8 Guests
1500 ft²
- Parking
- Pool
- Ocean View
- View
US $193/Night
7 Nights - US $1,351
House
- Orlando
- ·
- Clear Creek
- 0.42 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
1636.11 ft²
- Parking
- Pool
- Spa
- Balcony/Terrace
US $108/Night
7 Nights - US $756
New
House
- Orlando
- ·
- Four Corners
- 2.83 mi to center
4 Bedrooms
2 Baths
9 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $137/Night
7 Nights - US $959
House
- Orlando
- ·
- Clear Creek
- 0.26 mi to center
10.0Exceptional
(28 Reviews)
3 Bedrooms
3 Baths
8 Guests
1500 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $193/Night
7 Nights - US $1,351
House
- Orlando
- ·
- Four Corners
- 2.47 mi to center
10.0Exceptional
(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $195/Night
7 Nights - US $1,364
House
- Orlando
- ·
- Four Corners
- 3.41 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
1989 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $192/Night
7 Nights - US $1,341
Instantly Bookable Holiday Homes in Weston Hills
Over 1720+ Instantly Bookable Holiday Homes in or Near Weston Hills
New
House
- Orlando
- ·
- Four Corners
- 5.22 mi to center
10.0Exceptional
(6 Reviews)
4 Bedrooms
3 Baths
8 Guests
1828 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $277/Night
7 Nights - US $1,936
House
- Orlando
- ·
- Four Corners
- 3.10 mi to center
10.0Exceptional
(2 Reviews)
7 Bedrooms
5 Baths
15 Guests
3286 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $359/Night
7 Nights - US $2,512
New
Villa
- Orlando
- ·
- Four Corners
- 3.18 mi to center
10 Bedrooms
8 Baths
26 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $923/Night
7 Nights - US $6,460
New
Villa
- Orlando
- ·
- Four Corners
- 3.19 mi to center
10 Bedrooms
8 Baths
22 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $922/Night
7 Nights - US $6,457
New
Villa
- Orlando
- ·
- Four Corners
- 3.12 mi to center
10 Bedrooms
8 Baths
20 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $838/Night
7 Nights - US $5,866
New
House
- Orlando
- ·
- Four Corners
- 3.39 mi to center
10 Bedrooms
8 Baths
20 Guests
4382 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $814/Night
7 Nights - US $5,699
New
House
- Orlando
- ·
- Four Corners
- 3.49 mi to center
10 Bedrooms
8 Baths
28 Guests
4382 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $689/Night
7 Nights - US $4,820
New
Villa
- Orlando
- ·
- Four Corners
- 3.37 mi to center
5 Bedrooms
5 Baths
13 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $651/Night
7 Nights - US $4,557
New
House
- Orlando
- ·
- Four Corners
- 3.41 mi to center
6 Bedrooms
4 Baths
16 Guests
3127 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $530/Night
7 Nights - US $3,707
Book a Last Minute Place to Stay in Weston Hills
About Casai's Private Villas and Holiday Rentals in Weston Hills
Discover more than 2688 vacation rentals available in Weston Hills. 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 Weston Hills.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Weston Hills, 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 Weston Hills. On average, places to stay near Weston Hills offer 2548.47 ft², with nightly prices averaging US $358.
With Casai, finding and comparing holiday rentals in Weston Hills is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Weston Hills
| Type | Count |
|---|---|
| Vacation Homes | 1985 |
| Villas | 544 |
| Holiday Apartments | 82 |
| Cottages | 3 |
Use these Quick Filters to Find a Holiday Rental in Weston Hills
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Weston Hills.
Weather in Weston Hills, FL
View the weather forecast for Weston Hills before booking your Weston Hills Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Weston Hills?
What are the top holiday rentals in Weston Hills?
With numerous options available in Weston Hills, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Weston Hills:
- NEW - Luxury decorated villa with amazing view, private pool and spa
- Disney-Area Retreat - 5BR 3.5 Bath Villa w/Pool, Spa & Game Room
- Orlando Area 4 BR/3 BA Villa - Pool, Spa, Game Room, Wi-Fi, Gated Community
- Hidden Waterfront Oasis - 18 minutes to the Disney Entrance!
- Peaceful Lakeside Pool Villa w/Star Wars Games Room Near Disney
- Beautiful Townhouse with Splash Pool Close to Orlando Attractions
- Summer Bay Resort Vacation Rental, Minutes from Disney
- Spacious 5BR Villa w/South-Facing Pool, Spa & Game Room Near Disney
- Luxurious Executive Villa 20 mins from Disney, Private Pool/Spa, Games Room
- Private South-Facing Pool & Spa - Quiet Disney Villa - 6 Miles to Parks
How many holiday rentals have private pools in Weston Hills?
Discover a selection of holiday rentals with private pools near Weston Hills 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.
- Disney Getaway! Private Pool & Themed Bedrooms. Book Now! #WC91
- 5BR Resort Townhome with Private Pool!
- Clermont Area Vacation Homes by Shine FM
- Last Minute Disney Getaway! Private Pool & Game Room. Book Now! #121741
Which holiday homes in Weston Hills are best for families?
If you're searching for a family-friendly holiday home in Weston Hills, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Weston Hills:
- Disney Getaway! Private Pool & Themed Bedrooms. Book Now! #WC91
- Magical 5BR w Pool Minutes from Disney 16140
- Clermont Area Vacation Homes by Shine FM
How many Casai.com holiday rentals are available in Weston Hills?
As of 2026, Casai boasts over 2688 properties listed in the Weston Hills area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Weston Hills.
People Also Ask
Map
