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

Lobby
Bar (on property)
Pool
Private kitchen
Exceptional
(120 reviews)

7 Bedroom 6 Bath Vacation Villa, Minutes from Disney World!

Kissimmee

6% off
AU$4,750
for 7 nights, 1 home
AU$679 per night
includes taxes & fees
7 Bedroom 6 Bath Vacation Villa, Minutes from Disney World!
Fully equipped kitchen
Bronson Clubhouse lazy river, community pool, and children's pirate playscape
Bronson Clubhouse Bar & Grill
Bronson Gym open to guest 9a to 9pm
Exceptional
(53 reviews)

NEW 9Bdrm Themed w Arcade near Disney & Universal

Kissimmee

8% off
AU$12,945
for 7 nights, 1 home
AU$1,849 per night
includes taxes & fees
NEW 9Bdrm Themed w Arcade near Disney & Universal
Dining
Pool
Exterior
Pool
Exceptional
(87 reviews)

9BR Resort Villa / Private Pool & Spa / Sleeps 22 / Near Disney

Kissimmee

8% off
AU$7,213
for 7 nights, 1 villa
AU$1,030 per night
includes taxes & fees
9BR Resort Villa / Private Pool & Spa / Sleeps 22 / Near Disney
Garage-turned-games-room with, foosball, game consoles and more!
Luxury Patio with Private Pool and Hot Tub, Games, Smart TVs, BBQ and more.
Large Capacity Living Area with 3 Big Screen TVs
Private Movie Theatre with giant projection screen and cinema style recliners
Very good
(16 reviews)

Upstay Family Resort Mansion- Pool, Games, Theater

Kissimmee

8% off
AU$19,679
for 7 nights, 1 home
AU$2,811 per night
includes taxes & fees
Upstay Family Resort Mansion- Pool, Games, Theater
The Emerald Island Resort fountain at our entrance
Clubhouse and Pool
Living room
Sparkling pool with all day full sun
Exceptional
(124 reviews)

SUNSHINE 🌞 and SMILES😎 - 5 mi to Disney, 4 bdrm / 3 bath, Private Pool

Kissimmee

8% off
AU$4,577
for 7 nights, 1 home
AU$654 per night
includes taxes & fees
SUNSHINE 🌞 and SMILES😎 - 5 mi to Disney, 4 bdrm / 3 bath, Private Pool
Outdoor swimming pool and jaccuzi hot tub
Living room with smart TV and high speed internet
Games room with billiards table
King bedroom with en-suite bathroom
Exceptional
(6 reviews)

Upstay: Large Resort Home w Private Pool & Hot Tub

Kissimmee

8% off
AU$9,706
for 7 nights, 1 home
AU$1,387 per night
includes taxes & fees
Upstay: Large Resort Home w Private Pool & Hot Tub
Upstairs Movie Lounge with Big Screen TV
Large furnished sundeck with private swimming pool
In-home game room arcade with billiards, air hockey, arcade basketball, and more
Roku TVs with Complimentary Cable and WiFI
Wonderful
(20 reviews)

Upstay: Resort Mansion w Pool Games Room and BBQ

Davenport

8% off
AU$7,546
for 7 nights, 1 home
AU$1,078 per night
includes taxes & fees
Upstay: Resort Mansion w Pool Games Room and BBQ
Room
Living area
Pool
Exterior
Wonderful
(24 reviews)

Magical charm couple miles away from Disney

Kissimmee

7% off
AU$2,728
for 7 nights, 1 home
AU$390 per night
includes taxes & fees
Magical charm couple miles away from Disney
In-House Mickey Mouse Themed Movie Room
Lake Views from Private Sundeck with Private Swimming Pool
Sports Themed Games Room
Open concept layout
Wonderful
(29 reviews)

Waterfront Family Mansion w BBQ, Games Room & Pool

Kissimmee

8% off
AU$7,880
for 7 nights, 1 home
AU$1,126 per night
includes taxes & fees
Waterfront Family Mansion w BBQ, Games Room & Pool
Spacious open concept design
Private Swimming Pool and Screened-in Patio
Garage-turned-games-room
Large Capacity Dining Area with Patio Access
Exceptional
(5 reviews)

Resort Home w Pool, Games, BBQ - Near Disney!

Kissimmee

8% off
AU$6,685
for 7 nights, 1 home
AU$955 per night
includes taxes & fees
Resort Home w Pool, Games, BBQ - Near Disney!
No Quarters Needed!
Professional Arcade Room
Brand New in 2024
All Games Set to "Free-Play"
Exceptional
(25 reviews)

Welcome to The Windsor Treasure with Professional Arcade Room! Brand New 2024!

Kissimmee

10% off
AU$8,535
for 7 nights, 1 villa
AU$1,219 per night
includes taxes & fees
Welcome to The Windsor Treasure with Professional Arcade Room! Brand New 2024!
Dining
Pool
Exterior
Private kitchen
Wonderful
(159 reviews)

Charming Home Perfect for Families! 3/3 with Pool

Davenport

7% off
AU$1,960
for 7 nights, 1 home
AU$280 per night
includes taxes & fees
Charming Home Perfect for Families! 3/3 with Pool
Exterior
Pool
Golf
Private kitchen
Exceptional
(24 reviews)

ChampionsGate Townhome + Fast WiFi, Beautiful Kitchen. Oasis Pool & Jacuzzi.

Davenport

6% off
AU$3,961
for 7 nights, 1 home
AU$566 per night
includes taxes & fees
ChampionsGate Townhome + Fast WiFi, Beautiful Kitchen. Oasis Pool & Jacuzzi.
Lots of seating in the shade with ceiling fan to help cool off all the Muggles.
Access to the community pool and waterslide are included free of charge with your rental. The community pool is a 15 minute walk from the house and has free onsite parking.
Gather your wizards here for the perfect vacation!
Welcome to Villa 9 3/4.
Exceptional
(96 reviews)

Harry Potter Villa - 10 Mins to Disney

Kissimmee

8% off
AU$6,886
for 7 nights, 1 villa
AU$984 per night
includes taxes & fees
Harry Potter Villa - 10 Mins to Disney
Foyer
community pool/splashpad/waterslide
Back yard lanai with patio furniture
Front view of house
Exceptional
(91 reviews)

😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞

Kissimmee

8% off
AU$3,480
for 7 nights, 1 home
AU$497 per night
includes taxes & fees
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
The Lobby Sushi Bar - located in The Grande lobby. Open Monday - Saturday 5 - 10pm
The Grande foyer
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Exceptional
(127 reviews)

Reunion South facing pool home 3 bed/3.5 baths

Kissimmee

8% off
AU$3,194
for 7 nights, 1 home
AU$456 per night
includes taxes & fees
Reunion South facing pool home 3 bed/3.5 baths
Gym
Pool
Upstairs King Bedroom with balcony
Living room
Exceptional
(87 reviews)

Private End Unit Near Disney - Regal Oaks Resort Pool - Sleeps 8

Kissimmee

7% off
AU$2,351
for 7 nights, 1 home
AU$336 per night
includes taxes & fees
Private End Unit Near Disney - Regal Oaks Resort Pool - Sleeps 8
Living area
Exterior
Pool
Private kitchen
Exceptional
(136 reviews)

Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi

Kissimmee

6% off
AU$3,255
for 7 nights, 1 home
AU$465 per night
includes taxes & fees
Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi
Dinning space
modern and comfort
Open kitchen and dinning area
Living room
Exceptional
(168 reviews)

New Vista Cay 3 Bedroom 2 bath - Next to Epic Universal / Conv. Center - Ocean

Orlando

7% off
AU$3,147
for 7 nights, 1 apartment
AU$450 per night
includes taxes & fees
New Vista Cay 3 Bedroom 2 bath - Next to Epic Universal / Conv. Center - Ocean
Sports court
Exterior
Pool
Interior
Exceptional
(190 reviews)

Designer-Renovated Condo in a Gorgeous Tropical Oasis!

Davenport

5% off
AU$1,572
for 7 nights, 1 apartment
AU$225 per night
includes taxes & fees
Designer-Renovated Condo in a Gorgeous Tropical Oasis!
Children’s area
Property grounds
Pool
Living area
Exceptional
(178 reviews)

Beautifully updated large family condo with King suite - 15 minutes to Disney

Davenport

7% off
AU$1,850
for 7 nights, 1 apartment
AU$264 per night
includes taxes & fees
Beautifully updated large family condo with King suite - 15 minutes to Disney
Private kitchen
Pool
Fitness facility
Children’s area
Exceptional
(79 reviews)

2 bed, 2 bath condo close to Disney and other theme parks Orlando

Kissimmee

8% off
AU$1,378
for 7 nights, 1 apartment
AU$197 per night
includes taxes & fees
2 bed, 2 bath condo close to Disney and other theme parks Orlando
Living area
Exterior
Private kitchen
Interior
Exceptional
(81 reviews)

*8bd Themed-Theater-Arcade-Prvt Pool/Spa-Disney!

Kissimmee

8% off
AU$8,580
for 7 nights, 1 home
AU$1,226 per night
includes taxes & fees
*8bd Themed-Theater-Arcade-Prvt Pool/Spa-Disney!
Fully equipped exercise room
Waterslide and pool area
Private Balcony
Dinning Table with 6 Chairs
Excellent
(171 reviews)

Mickey's Hangout - Quiet but close to Clubhouse & Pool - Under NEW MANAGEMENT

Kissimmee

7% off
AU$2,077
for 7 nights, 1 apartment
AU$297 per night
includes taxes & fees
Mickey's Hangout - Quiet but close to Clubhouse & Pool - Under NEW MANAGEMENT
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More 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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