Webster Holiday Rentals

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Holiday Rentals in Webster

Siena at Bella Collina

3.5 star property
9.8 out of 10, Exceptional, (67)
"Fantastic accommodation. "
The price is AU$576
includes taxes & fees
31 Aug - 1 Sept
Siena at Bella Collina

Peaceful Lakeside Pool Villa w/ Star Wars Games Room Near Disney

10.0 out of 10, Exceptional, (72)
"Had an awesome time in Orlando while staying at this very well appointed property. "
Peaceful Lakeside Pool Villa w/ Star Wars Games Room Near Disney

Hidden Waterfront Oasis - 18 minutes to the Disney Entrance!

10.0 out of 10, Exceptional, (95)
"The property was beautiful and had everything we needed and then some. The neighborhood was quiet and the backyard is incredibly serene and peaceful. Overall a great place! "
Hidden Waterfront Oasis - 18 minutes to the Disney Entrance!

Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

10.0 out of 10, Exceptional, (108)
"Great landlords, beautiful villa and great location "
Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

Private 5 Bedroom Villa Near Disney, free WI-FI 10% OFF LONG TERM RENTALS

9.4 out of 10, Exceptional, (129)
"This house was beautiful. The whole family loved it"
Private 5 Bedroom Villa Near Disney, free WI-FI 10% OFF LONG TERM RENTALS

Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

10.0 out of 10, Exceptional, (215)
"We loved our stay! The house is spacious, well stocked, clean and great location. We enjoyed relaxing on the lanai with the beautiful view of the golf course and pool. David is an excellent host! "
Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

Private Spacious Room in Home, with Pool-The Oasis Room

9.6 out of 10, Exceptional, (17)
" It a wonderful place "
The price is AU$168
includes taxes & fees
30 Aug - 31 Aug
Private Spacious Room in Home, with Pool-The Oasis Room

☀️Waterfront Villa on Quiet Cul-De-Sac–Beautiful, Spacious & Private, Games Rm🐠

9.8 out of 10, Exceptional, (221)
"Beautiful home !! Loved the pool and hot tub! Plenty of room for everyone! Enjoyed the view and quality time spent with one another! Would definitely recommend this home and look forward to coming back again!!"
☀️Waterfront Villa on Quiet Cul-De-Sac–Beautiful, Spacious & Private, Games Rm🐠

AWESOME HOUSE 5 bed/4 bath, south facing pool with spa & games room

10.0 out of 10, Exceptional, (146)
"Very nice and convenient house fill with fun stuff."
AWESOME HOUSE 5 bed/4 bath, south facing pool with spa & games room

2 King 2 Twin 1 Queen Enormous Deck 3 BD Lakeview House at Waterfront Park

10.0 out of 10, Exceptional, (17)
"We loved staying at this beautiful home! It is so well decorated. Seems like they thought of just about everything! We definitely plan to stay here again."
2 King 2 Twin 1 Queen Enormous Deck 3 BD Lakeview House at Waterfront Park

A perfect place to watch the Sunset

9.8 out of 10, Exceptional, (111)
"Perfect home to come back to after a day in Disney! This was our second time staying here and we will be back"
A perfect place to watch the Sunset

Exclusive Executive Disney Villa with Large Pool Deck

9.6 out of 10, Exceptional, (87)
"Lovely place. Convenient location. "
Exclusive Executive Disney Villa with Large Pool Deck

Lake View Retreat Loaded For Fun, with STUNNING Views!

10.0 out of 10, Exceptional, (35)
"Worked out well for golfing trip just a great place to stay and the host or excellent"
The price is AU$1,165
includes taxes & fees
1 Sept - 2 Sept
Lake View Retreat Loaded For Fun, with STUNNING Views!

WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+

9.8 out of 10, Exceptional, (111)
"We had a great stay. Thank you! "
WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+

Cozy, Close to downtown Lake View home.

9.6 out of 10, Exceptional, (16)
"House was clean and organized. Fun view of the lake!"
Cozy, Close to downtown Lake View home.

Vacation Home with luxurious pool in The Villages, Florida!

10.0 out of 10, Exceptional, (45)
"We had a great time enjoying the beautiful pool and outdoor barbeque area. The home was very comfortable for six adults. Jeff and Aggie were wonderful hosts and responded quickly to any questions we had. This is a beautiful home for a family get away."
The price is AU$996
includes taxes & fees
2 Sept - 3 Sept
Vacation Home with luxurious pool in The Villages, Florida!

5 Minute Golf Cart Ride To Brownwood, Restaurants, Entertainment

10.0 out of 10, Exceptional, (58)
"Great property; great location "
5 Minute Golf Cart Ride To Brownwood, Restaurants, Entertainment

Heated Pool house in Lake Panasoffkee

9.6 out of 10, Exceptional, (37)
"Great clean house, thanks for having us!"
The price is AU$534
includes taxes & fees
8 Sept - 9 Sept
Heated Pool house in Lake Panasoffkee

Our Village Gem-5 Star- Elegant & Comfortable- Very Close to Sumter Squ.

10.0 out of 10, Exceptional, (116)
"Everything was very nice, no issues at all."
Our Village Gem-5 Star- Elegant & Comfortable- Very Close to Sumter Squ.

Paradise awaits! Townhome at Epperson Lagoon in breathtaking Wesley Chapel!

2.0 star property
9.0 out of 10, Wonderful, (8)
"Had a girls trip and went to mirada lagoon. Had an amazing stay!"
The price is AU$598
includes taxes & fees
9 Sept - 10 Sept
Paradise awaits! Townhome at Epperson Lagoon in breathtaking Wesley Chapel!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Webster Hotel Reviews

Find out more about Webster

Find out more about Webster

Everything you need to know about Webster holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Webster holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Webster holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Webster holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Webster. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Webster holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Webster holiday rentals we have selected for you start as low as AU$168 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Webster rentals

At Expedia, we put the best Webster holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Webster rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Webster holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Webster. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Webster?

Yes, there are holiday rentals close to the most popular sights in Webster, or you can select a more secluded option if you're looking for a relaxing stay. Webster is known for its shopping.

What are some of the best holiday rentals that Webster has to offer?

Peaceful Lakeside Pool Villa w/ Star Wars Games Room Near Disney : This holiday home rental outside of Webster is located on a lake, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Webster?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Webster stay.

What’s there to see and do in Webster?

Explore the area and family-friendly sights such as Giraffe Ranch, or get out into nature at a spot like Withlacoochee Trail State Park. Webster Westside Flea Market and Florida National Cemetery are a couple of places you'll find in the wider area.

What’s a holiday rental in Webster like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Webster. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family gatherings.