Best Vacation Homes in Windsor Palms
House
10.0(52 Reviews)
4 Bedrooms
3 Baths
10 Guests
1834 ft²
Private Pool
Hot Tub
Fireplace/Heating
Pool
US $362/Night
7 Nights - US $2,536
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
8 Guests
1829.86 ft²
Oceanfront- Fireplace/Heating
- Pool
Ocean View
US $397/Night
7 Nights - US $2,777
Villa
10.0(1 Review)
4 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pool
Pet Friendly
Kitchen
US $148/Night
7 Nights - US $1,033
Condo
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1400 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $158/Night
7 Nights - US $1,103
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
1571.53 ft²
- Hot Tub
Spa- Fireplace/Heating
- Pool
US $351/Night
7 Nights - US $2,455
House
10.0(2 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Pool
- Kitchen
Parking
US $284/Night
7 Nights - US $1,989
New
House
9.8(189 Reviews)
3 Bedrooms
3 Baths
6 Guests
1440 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $228/Night
7 Nights - US $1,595
New
Villa
8.8(20 Reviews)
4 Bedrooms
3 Baths
8 Guests
2125 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $259/Night
7 Nights - US $1,810
Windsor Palms Luxury Rentals
House
5 Bedrooms
4 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,420/Night
7 Nights - US $9,939
US $1,162/Night
7 Nights - US $8,137
House
1 Bedroom
2 Baths
4 Guests
1054.86 ft²
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $1,010/Night
7 Nights - US $7,070
House
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
Balcony/Terrace
US $966/Night
7 Nights - US $6,759
Villa
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
US $805/Night
7 Nights - US $5,633
Villa
10.0(3 Reviews)
6 Bedrooms
3 Baths
12 Guests
2434 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $746/Night
7 Nights - US $5,221
House
3 Bedrooms
3 Baths
6 Guests
1076.39 ft²
- Private Pool
- Pool
- Parking
- Air Conditioner
US $672/Night
7 Nights - US $4,704
House
9.0(64 Reviews)
6 Bedrooms
3 Baths
14 Guests
2434 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $662/Night
7 Nights - US $4,634
Windsor Palms Pet Friendly Vacation Rentals
House
10.0(185 Reviews)
4 Bedrooms
3 Baths
10 Guests
1834 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $299/Night
7 Nights - US $2,090
House
10.0(1 Review)
3 Bedrooms
3 Baths
7 Guests
1442.36 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $256/Night
7 Nights - US $1,793
House
8.0(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $577/Night
7 Nights - US $4,037
House
10.0(10 Reviews)
4 Bedrooms
2 Baths
8 Guests
1567 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $281/Night
7 Nights - US $1,970
House
9.8(16 Reviews)
4 Bedrooms
3 Baths
8 Guests
1786.81 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $199/Night
7 Nights - US $1,395
House
10.0(6 Reviews)
4 Bedrooms
3 Baths
8 Guests
1842 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $315/Night
7 Nights - US $2,207
House
10.0(2 Reviews)
5 Bedrooms
4 Baths
11 Guests
2256 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $415/Night
7 Nights - US $2,906
House
10.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
2000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $437/Night
7 Nights - US $3,062
Windsor Palms Large Vacation Homes
New
House
5 Bedrooms
4 Baths
10 Guests
2131 ft²
- Private Pool
- Pool
- Kitchen
- Parking
US $333/Night
7 Nights - US $2,333
New
Villa
10.0(2 Reviews)
1 Bedroom
3 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
Security/Safety
US $248/Night
7 Nights - US $1,733
House
Room for the Whole Family 3 Master Suites and Two Themed Children's Rooms, Private South-Facing Pool
9.6(21 Reviews)
5 Bedrooms
4 Baths
10 Guests
2844 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $230/Night
7 Nights - US $1,608
House
10.0(226 Reviews)
7 Bedrooms
4 Baths
15 Guests
2200 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $431/Night
7 Nights - US $3,019
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
1829.86 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $331/Night
7 Nights - US $2,319
House
10.0(223 Reviews)
5 Bedrooms
4 Baths
11 Guests
2900 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $439/Night
7 Nights - US $3,070
Villa
10.0(220 Reviews)
4 Bedrooms
3 Baths
8 Guests
1835 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $218/Night
7 Nights - US $1,528
House
10.0(131 Reviews)
4 Bedrooms
3 Baths
10 Guests
1875 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $272/Night
7 Nights - US $1,906
Why Choose Rent By Owner for your Windsor Palms Vacation Rental Homes?
What makes our Vacation Rentals special?
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Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Windsor Palms Vacation Rentals
Where are the best neighborhoods to stay in Windsor Palms?
When choosing where to stay in Windsor Palms, Kissimmee, Florida, you’ll find a vibrant neighborhood that offers convenient access to nearby attractions and a welcoming atmosphere. This community is ideal for travelers seeking comfortable and well-equipped vacation rentals in close proximity to Orlando’s popular destinations. Staying here provides a seamless experience, combining the comfort of home with the convenience of being near major highways and local amenities. Whether you're visiting for relaxation or adventure, Windsor Palms in Kissimmee ensures a memorable Florida getaway with a variety of rental options designed to meet your needs.
West Kissimmee
Located just outside the main attractions, this area offers convenient access to the region’s popular theme parks and entertainment venues. Here, you can enjoy a peaceful setting while remaining close to the key destinations that make this part of Florida a top vacation spot.
View 15503+ Rentals in West KissimmeeBest Times to Visit Windsor Palms
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, as seasonal variations and local events in this destination influence the perfect window for booking your ideal vacation rental in Windsor Palms, Kissimmee, Florida.
Peak Season Highlights
Spring (March to May)
During spring, you can enjoy warm weather and pleasant evenings, making it an ideal time for outdoor activities and exploring the area’s attractions.
Average Temperature Daytime: high 75°F to 85°F - Nighttime: mid 55°F to 65°F
Winter Holidays (December to February)
This season offers cooler but comfortable temperatures, perfect for those seeking a festive atmosphere combined with leisure in this popular destination.
Average Temperature Daytime: high 65°F to 75°F - Nighttime: mid 45°F to 55°F
Off-Season Highlights
Summer (June to August)
In the summer months, the region experiences hot temperatures, providing excellent conditions for sunbathing and water-based activities while benefiting from lower crowd levels.
Average Temperature Daytime: high 85°F to 95°F - Nighttime: mid 70°F to 75°F
Fall (September to November)
Fall sees slightly cooler temperatures, making it a peaceful time to visit while enjoying fewer tourists and more relaxed exploration of the area’s amenities.
Average Temperature Daytime: high 70°F to 80°F - Nighttime: mid 50°F to 60°F
Weekly Weather Forecast for Windsor Palms
How to Book Your Windsor Palms Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windsor Palms
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to a private outdoor swimming pool perfect for relaxing after a day at nearby theme parks.
- Take advantage of well-maintained tennis courts for active outdoor recreation in the area.
- Relax on spacious sun decks and lounge areas that overlook lush landscaped grounds.
- Utilize outdoor barbecue grills for convenient and enjoyable family cookouts.
- Explore scenic walking paths and jogging trails within the community grounds.
- Benefit from beautifully maintained gardens and picnic areas ideal for outdoor gatherings.
- Make use of the children's play zones designed for safe and fun outdoor activities for kids.
Top Attractions Around Windsor Palms
What attractions are nearby?
Here, you can enjoy a variety of nearby activities and attractions that make your stay in this vibrant destination truly memorable.
Family Activities
- Disney World Orlando: Just a short drive away, this world-famous theme park offers magical experiences and attractions perfect for family fun in the region.
- Celebration Town Center: Explore this charming community with its lively shops, dining options, and outdoor activities suitable for all ages here in the area.
- Wild Florida Airboats & Gator Park: Experience an adventurous airboat tour through the Everglades, where your family can spot local wildlife and learn about the region's natural environment.
- Medieval Times Dinner & Tournament: Enjoy an interactive dinner show where your family can witness exciting medieval performances right in the region's entertainment district.
Adult Activities
- Golf at Falcon's Fire Golf Club: Tee off at one of the top-rated courses in the region, offering a challenging and scenic experience for golf enthusiasts staying nearby.
- Relaxation at local spas: Indulge in rejuvenating treatments at nearby spas that cater to adults seeking pampering and wellness during their stay here.
- Fine dining experiences: Explore a variety of upscale restaurants and eateries in the area, perfect for enjoying a sophisticated night out or leisurely dinner.
- Shopping excursions: Discover popular shopping centers and outlets close to your vacation rental, ideal for retail therapy and gathering souvenirs from your trip here.
Windsor Palms Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Attractions: Research nearby theme parks and entertainment options to maximize your time and enjoy everything this region has to offer.
- Choose a Well-Equipped Rental: Select a vacation rental with family-friendly amenities such as a private pool, kitchen, and spacious living areas for a comfortable stay in the area.
- Explore Transportation Options: Consider renting a car or utilizing local shuttle services to easily access popular spots throughout here and avoid unnecessary delays.
- Make the Most of On-Site Amenities: Take advantage of community facilities like pools, fitness centers, and recreational areas to enhance your vacation experience in this destination.
Transportation Options
- Rental Car Services: Convenient options like Enterprise, Hertz, and Avis are available nearby, giving you flexibility to explore the region at your own pace.
- Shuttle Services: Shared shuttle providers operate regularly to and from popular destinations, making transportation effortless during your stay here.
- Public Transit: The area's local bus system offers affordable travel within Kissimmee and connects you easily to major attractions in Orlando.
- Taxi and Rideshare: Taxi services and rideshare platforms like Uber and Lyft provide quick, reliable transportation options for getting around the destination comfortably.
Local Customs Options
- Gator Safety Etiquette: Visitors should exercise caution and respect local wildlife, especially alligators, which are an integral part of the natural environment here.
- Respect for Leisure Spaces: Maintaining cleanliness and order in community parks and recreational areas reflects the friendly spirit of this region.
- Festive Celebration Customs: Participating in local holiday and festival traditions can enrich your experience and deepen your connection to the area’s vibrant community.
- Quiet Hours Policy: Observing designated quiet times ensures a peaceful atmosphere for all vacationers enjoying their stay in the region.
Windsor Palms Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Windsor Palms?
There are a lot of options in Windsor Palms. If you plan on staying in the Windsor Palms area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor Palms:
- Water View - Pool & Spa - 3.5 miles to Disney - BBQ
- 5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
- JUST RENOVATED!✦Spacious✦Clean✦Private True South Pool/Spa✦5 Miles to Disney
- Magical Getaway - 4BR/3BA with Pool/Spa, Wifi, Games Room
- WINDSOR PALMS - IMMACULATE 4/3 POOL HOME NEAR CLUBHOUSE
- Minutes to Disney-5-Star-Man-Gated-No Rear Neighbors-Windsor Palms
- POOL HOME - Luxury Windsor Palms Resort - 6 miles to Disney! POOL HEAT INCLUDED!
- Gated community with tons of resort amenities, minutes from Walt Disney World!
- Amazing Disney Dream Getaway in Windsor Palms! Dates in Aug/Sept still open!
- RENOVATED!✦Unique & Roomy✦Private Fenced True South Salt Pool✦5 Miles to Disney
2. How many vacation rentals have private pools in Windsor Palms?
There are 633 vacation rentals with private pools near Windsor Palms. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windsor Palms are best for families?
If you are looking for a family-friendly vacation home in Windsor Palms, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor Palms:
4. How many Rentbyowner vacation rentals are available in Windsor Palms?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1339 in the Windsor Palms area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windsor Palms.
5. What is the cancellation policy for booking a vacation rental in Windsor Palms?
The cancellation policy varies depending on the individual listing you choose. Please review the specific property's cancellation terms on the listing page or contact the owner directly to understand your options and any potential fees.
6. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning charges, service fees, or taxes may apply. These details are typically outlined during the booking process or on the property’s listing page, so be sure to review them carefully before confirming your reservation.
7. Can I modify my reservation after booking a vacation rental in the region?
Modification policies differ by listing. You should contact the property owner or review the booking terms on the listing page to determine if changes are permitted and what the procedures entail.
8. What amenities can I expect from vacation rentals in this destination?
Amenities vary by property but often include features like private pools, fully equipped kitchens, Wi-Fi, and entertainment options. To see what is available at each rental, refer to the detailed listing descriptions or contact the owner directly.
9. Is there a minimum stay requirement for vacation rentals here?
Minimum stay requirements depend on the specific property and season. Details about stay length are provided on each listing, so review these terms carefully when selecting your accommodation or reach out to the owner for clarification.
Windsor Palms Top Rated Vacation Rentals
House
10.0(323 Reviews)
4 Bedrooms
3 Baths
8 Guests
1800 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $328/Night
7 Nights - US $2,299
House
10.0(219 Reviews)
4 Bedrooms
3 Baths
8 Guests
1942 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $234/Night
7 Nights - US $1,638
House
10.0(190 Reviews)
4 Bedrooms
3 Baths
8 Guests
1835 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $280/Night
7 Nights - US $1,962
Condo
10.0(180 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $186/Night
7 Nights - US $1,305
House
10.0(176 Reviews)
4 Bedrooms
3 Baths
8 Guests
1853 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $274/Night
7 Nights - US $1,921
House
10.0(133 Reviews)
4 Bedrooms
3 Baths
8 Guests
1800 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $403/Night
7 Nights - US $2,818
House
10.0(132 Reviews)
4 Bedrooms
3 Baths
8 Guests
1834 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $294/Night
7 Nights - US $2,061
Villa
10.0(125 Reviews)
4 Bedrooms
3 Baths
10 Guests
1874 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $460/Night
7 Nights - US $3,222
