Williamsburg holiday homes

We found 34,326 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:25 Dec - 1 Jan

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
Excellent
(15 reviews)

Upstay Family Resort Mansion- Pool, Games, Theater

Kissimmee

8% off
NZ$30,482
for 7 nights, 1 home
NZ$4,355 per night
includes taxes & fees
Upstay Family Resort Mansion- Pool, Games, Theater
Interior
Pool
Interior
Fitness facility
Exceptional
(35 reviews)

Beautiful Home with a South-Facing Heated Pool-Jacuzzi & BBQ Grill included

Davenport

7% off
NZ$8,178
for 7 nights, 1 villa
NZ$1,168 per night
includes taxes & fees
Beautiful Home with a South-Facing Heated Pool-Jacuzzi & BBQ Grill included
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
NZ$14,142
for 7 nights, 1 home
NZ$2,020 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
NZ$11,229
for 7 nights, 1 home
NZ$1,604 per night
includes taxes & fees
Upstay: Resort Mansion w Pool Games Room and BBQ
Pool
Exterior
Living area
Pool
Exceptional
(5 reviews)

Gorgeous private home, dog-friendly, private pool & close to parks

Davenport

7% off
NZ$5,996
for 7 nights, 1 home
NZ$857 per night
includes taxes & fees
Gorgeous private home, dog-friendly, private pool & close to parks
The in house loft movie theatre has a popcorn machine and cool mood lighting.
Hot Tub Jacuzzi and Private Swimming Pool
Mario Brothers Theme Room
Avatar Themed Game Room with Pool Table, Arcade Games and More!
Very good
(20 reviews)

Upstay: Resort-Style 12BR Villa—Bella Vida Resort

Kissimmee

8% off
NZ$20,849
for 7 nights, 1 home
NZ$2,978 per night
includes taxes & fees
Upstay: Resort-Style 12BR Villa—Bella Vida Resort
Large Capacity Family Dining Table
Private Swimming Pool and Furnished Sundeck Patio
Large Spacious Bedrooms
Private Games Room with Table Tennis and More
Wonderful
(17 reviews)

Family Resort Home w Pool, BBQ & Game Room

Davenport

8% off
NZ$6,642
for 7 nights, 1 home
NZ$949 per night
includes taxes & fees
Family Resort Home w Pool, BBQ & Game Room
Pool
Private kitchen
Terrace/patio
Living area
Very good
(6 reviews)

Modern Orlando Retreat – Minutes to Disney, Universal & All the Magic!”

Orlando

8% off
NZ$4,334
for 7 nights, 1 home
NZ$619 per night
includes taxes & fees
Modern Orlando Retreat – Minutes to Disney, Universal & All the Magic!”
Dining
Community clubhouse
Room
Private kitchen
Exceptional
(95 reviews)

Flash Sale - Themed 9BR New Home@Disney, Home Theater, Private Pool/SPA, Game Rm

Kissimmee

8% off
NZ$8,982
for 7 nights, 1 home
NZ$1,283 per night
includes taxes & fees
Flash Sale - Themed 9BR New Home@Disney, Home Theater, Private Pool/SPA, Game Rm
Room
Pool
Room
Room
Exceptional
(8 reviews)

4BR Luxury Solara Resort Retreat, Pool, Disney - 1798 TP

Kissimmee

13% off
NZ$4,730
for 7 nights, 1 home
NZ$676 per night
includes taxes & fees
4BR Luxury Solara Resort Retreat, Pool, Disney - 1798 TP
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
NZ$9,742
for 7 nights, 1 home
NZ$1,392 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
NZ$14,062
for 7 nights, 1 villa
NZ$2,009 per night
includes taxes & fees
Welcome to The Windsor Treasure with Professional Arcade Room! Brand New 2024!
Room
Room
Pool
Pool
Very good
(11 reviews)

Magical Haven: Your Private Townhome with Pool 4321 QS

Kissimmee

13% off
NZ$4,350
for 7 nights, 1 home
NZ$621 per night
includes taxes & fees
Magical Haven: Your Private Townhome with Pool 4321 QS
Indoor Family Dining Area
Private Swimming Pool with Sun Loungers
King bedroom with en-suite bathroom
Living Room with Smart TV and High Speed Internet
Wonderful
(7 reviews)

Spacious 4BR Family Townhouse—Private Pool & BBQ

Kissimmee

8% off
NZ$8,007
for 7 nights, 1 home
NZ$1,144 per night
includes taxes & fees
Spacious 4BR Family Townhouse—Private Pool & BBQ
Living area
Pool
Room
Exterior
Excellent
(60 reviews)

Delightful Home, Close to Disney Parks

Kissimmee

6% off
NZ$1,986
for 7 nights, 1 home
NZ$284 per night
includes taxes & fees
Delightful Home, Close to Disney Parks
play areas for the kids
Welcome Home
free wifi, extended cable and long distance within Canada and USA
fully equipped kitchen
Wonderful
(36 reviews)

VB043 4 Bedroom, 3 Bath Townhouse

Kissimmee

10% off
NZ$2,504
for 7 nights, 1 home
NZ$358 per night
includes taxes & fees
VB043 4 Bedroom, 3 Bath Townhouse
Golf
Pool
Private kitchen
Exterior
Exceptional
(24 reviews)

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

Davenport

5% off
NZ$5,584
for 7 nights, 1 home
NZ$798 per night
includes taxes & fees
ChampionsGate Townhome + Fast WiFi, Beautiful Kitchen. Oasis Pool & Jacuzzi.
Master suite with a king size bed
Open space
open kitchen
Large granite countertop
Exceptional
(311 reviews)

Vista Cay 3 Bedroom, in front of new Epic Universe and conv Center - Sunset

Orlando

7% off
NZ$4,933
for 7 nights, 1 apartment
NZ$705 per night
includes taxes & fees
Vista Cay 3 Bedroom, in front of new Epic Universe and conv Center - Sunset
Room
Pool
Living area
Room
Wonderful
(12 reviews)

4826 LL - Storey Lake Dream 4BR Pool Home Near Disney

Kissimmee

13% off
NZ$4,707
for 7 nights, 1 home
NZ$672 per night
includes taxes & fees
4826 LL - Storey Lake Dream 4BR Pool Home Near Disney
Living area
Pool
Room
Games room
Very good
(21 reviews)

Exquisite 5 Bed Single Family with Private Pool - 8992 CC

Davenport

13% off
NZ$5,487
for 7 nights, 1 home
NZ$784 per night
includes taxes & fees
Exquisite 5 Bed Single Family with Private Pool - 8992 CC
Living area
Pool
Room
Room
Excellent
(9 reviews)

Champions Bliss: 5-Bed Marvel, Princess Themes, Private Pool

Davenport

13% off
NZ$5,168
for 7 nights, 1 home
NZ$738 per night
includes taxes & fees
Champions Bliss: 5-Bed Marvel, Princess Themes, Private Pool
Exterior
Pool
Private kitchen
Property grounds
Exceptional
(19 reviews)

Luxary villa close to disney

Kissimmee

7% off
NZ$3,487
for 7 nights, 1 villa
NZ$498 per night
includes taxes & fees
Luxary villa close to disney
3rd. bedroom with 2 queen size beds
Breakfast area
Master bedroom with king size bed
second bedroom with 2 twin beds
Exceptional
(257 reviews)

IN FRONT OF THEME PARKS - CLOSE TO POOL , CONV CENTER , INT'L DRIVE - SUNNY

Orlando

7% off
NZ$4,369
for 7 nights, 1 apartment
NZ$624 per night
includes taxes & fees
IN FRONT OF THEME PARKS - CLOSE TO POOL , CONV CENTER , INT'L DRIVE - SUNNY
Exterior
Property grounds
Pool
Living area
Exceptional
(178 reviews)

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

Davenport

8% off
NZ$2,935
for 7 nights, 1 apartment
NZ$419 per night
includes taxes & fees
Beautifully updated large family condo with King suite - 15 minutes to Disney
  • 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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Williamsburg holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Williamsburg to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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