Williamsburg holiday rentals
We found 34,287 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Williamsburg to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the amenities that you need and want for your stay, which might include parking and a pool. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts – Williamsburg
Showing deals for:18 Dec - 25 Dec

Exceptional
(120 reviews)
7 Bedroom 6 Bath Vacation Villa, Minutes from Disney World!
Kissimmee
AU$4,750
for 7 nights, 1 home
AU$679 per night
includes taxes & fees

Exceptional
(53 reviews)
NEW 9Bdrm Themed w Arcade near Disney & Universal
Kissimmee
AU$12,945
for 7 nights, 1 home
AU$1,849 per night
includes taxes & fees

Exceptional
(87 reviews)
9BR Resort Villa / Private Pool & Spa / Sleeps 22 / Near Disney
Kissimmee
AU$7,213
for 7 nights, 1 villa
AU$1,030 per night
includes taxes & fees

Very good
(16 reviews)
Upstay Family Resort Mansion- Pool, Games, Theater
Kissimmee
AU$19,679
for 7 nights, 1 home
AU$2,811 per night
includes taxes & fees

Exceptional
(124 reviews)
SUNSHINE 🌞 and SMILES😎 - 5 mi to Disney, 4 bdrm / 3 bath, Private Pool
Kissimmee
AU$4,577
for 7 nights, 1 home
AU$654 per night
includes taxes & fees

Exceptional
(6 reviews)
Upstay: Large Resort Home w Private Pool & Hot Tub
Kissimmee
AU$9,706
for 7 nights, 1 home
AU$1,387 per night
includes taxes & fees

Wonderful
(20 reviews)
Upstay: Resort Mansion w Pool Games Room and BBQ
Davenport
AU$7,546
for 7 nights, 1 home
AU$1,078 per night
includes taxes & fees

Wonderful
(24 reviews)
Magical charm couple miles away from Disney
Kissimmee
AU$2,728
for 7 nights, 1 home
AU$390 per night
includes taxes & fees

Wonderful
(29 reviews)
Waterfront Family Mansion w BBQ, Games Room & Pool
Kissimmee
AU$7,880
for 7 nights, 1 home
AU$1,126 per night
includes taxes & fees

Exceptional
(5 reviews)
Resort Home w Pool, Games, BBQ - Near Disney!
Kissimmee
AU$6,685
for 7 nights, 1 home
AU$955 per night
includes taxes & fees

Exceptional
(25 reviews)
Welcome to The Windsor Treasure with Professional Arcade Room! Brand New 2024!
Kissimmee
AU$8,535
for 7 nights, 1 villa
AU$1,219 per night
includes taxes & fees

Wonderful
(159 reviews)
Charming Home Perfect for Families! 3/3 with Pool
Davenport
AU$1,960
for 7 nights, 1 home
AU$280 per night
includes taxes & fees

Exceptional
(24 reviews)
ChampionsGate Townhome + Fast WiFi, Beautiful Kitchen. Oasis Pool & Jacuzzi.
Davenport
AU$3,961
for 7 nights, 1 home
AU$566 per night
includes taxes & fees

Exceptional
(96 reviews)
Harry Potter Villa - 10 Mins to Disney
Kissimmee
AU$6,886
for 7 nights, 1 villa
AU$984 per night
includes taxes & fees

Exceptional
(91 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee
AU$3,480
for 7 nights, 1 home
AU$497 per night
includes taxes & fees

Exceptional
(127 reviews)
Reunion South facing pool home 3 bed/3.5 baths
Kissimmee
AU$3,194
for 7 nights, 1 home
AU$456 per night
includes taxes & fees

Exceptional
(87 reviews)
Private End Unit Near Disney - Regal Oaks Resort Pool - Sleeps 8
Kissimmee
AU$2,351
for 7 nights, 1 home
AU$336 per night
includes taxes & fees

Exceptional
(136 reviews)
Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi
Kissimmee
AU$3,255
for 7 nights, 1 home
AU$465 per night
includes taxes & fees

Exceptional
(168 reviews)
New Vista Cay 3 Bedroom 2 bath - Next to Epic Universal / Conv. Center - Ocean
Orlando
AU$3,147
for 7 nights, 1 apartment
AU$450 per night
includes taxes & fees

Exceptional
(190 reviews)
Designer-Renovated Condo in a Gorgeous Tropical Oasis!
Davenport
AU$1,572
for 7 nights, 1 apartment
AU$225 per night
includes taxes & fees

Exceptional
(178 reviews)
Beautifully updated large family condo with King suite - 15 minutes to Disney
Davenport
AU$1,850
for 7 nights, 1 apartment
AU$264 per night
includes taxes & fees

Exceptional
(79 reviews)
2 bed, 2 bath condo close to Disney and other theme parks Orlando
Kissimmee
AU$1,378
for 7 nights, 1 apartment
AU$197 per night
includes taxes & fees

Exceptional
(81 reviews)
*8bd Themed-Theater-Arcade-Prvt Pool/Spa-Disney!
Kissimmee
AU$8,580
for 7 nights, 1 home
AU$1,226 per night
includes taxes & fees

Excellent
(171 reviews)
Mickey's Hangout - Quiet but close to Clubhouse & Pool - Under NEW MANAGEMENT
Kissimmee
AU$2,077
for 7 nights, 1 apartment
AU$297 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Williamsburg

Marriott's Grande Vista
Sleeps 4 · 1 bedroom

Lakeview Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms

Gorgeous Pool view/Waterfront/3 miles to Disney
Sleeps 8 · 3 bedrooms · 2+ bathrooms

Parc Corniche Condominium Suite Hotel
Sleeps 4 · 1 bedroom

Premier Resort Condos Near Universal
Sleeps 4 · 1 bedroom

Perfect Disney Vacation Home - Private Pool, Movie Theater, Gaming Room
Sleeps 23 · 9 bedrooms · 5 bathrooms
- 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
Frequently asked questions
When is the best time to visit Williamsburg for a holiday rental?
March is the most popular month to visit Williamsburg, as it falls right in the heart of the peak season, which spans from February to April. This period attracts a vibrant mix of families and adventure seekers who flock to the region to enjoy its rich history and exciting attractions. With the pleasant weather, often ranging from 10 to 20 degrees Celsius, this is an ideal time for outdoor activities such as exploring the historic sites, walking through Colonial Williamsburg, or enjoying the thrills at nearby theme parks.During these months, you'll find a variety of events and activities tailored to all ages, making it a lively time to experience the local culture. The area buzzes with energy, and popular attractions are running at full steam, ensuring plenty of options for both relaxation and adventure.For those looking for a more affordable yet equally enjoyable experience, consider visiting in October. This month offers comfortable temperatures and fewer crowds, allowing you to savour the beauty of fall foliage while exploring the historical aspects of the area at a leisurely pace. It's a wonderful time for scenic walks and enjoying the quieter side of Williamsburg without the hustle and bustle of the peak season.
What are the top attractions in Williamsburg, Florida, United States of America?
In Williamsburg, Florida, visitors can enjoy several attractions that showcase the area's charm. The nearby Walt Disney World® Resort is a major highlight, offering a variety of theme parks like Magic Kingdom and Epcot, which are easily accessible from the neighbourhood.For those interested in history and culture, the American Revolution-themed attractions of Colonial Williamsburg are a short drive away, providing a glimpse into 18th-century life with interactive exhibits and reenactments.Additionally, the scenic views and recreational opportunities at Lake Tohopekaliga in nearby Kissimmee make it a great spot for fishing, boating, and picnicking.
Are all fees included in the Williamsburg holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Williamsburg holiday homes with parking?
Stayz offers a wide selection of holiday homes in Williamsburg with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Williamsburg holiday homes?
You can find great discounts on holiday homes in Williamsburg on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Williamsburg holiday home booking on Stayz?
To find Williamsburg holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Williamsburg?
A long-stay holiday home in Williamsburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Williamsburg holiday home?
Book your Williamsburg holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Williamsburg?
Prices for holiday homes in Williamsburg vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Williamsburg to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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