Webster Holiday Rentals

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Holiday Rentals in Webster

Siena at Bella Collina
3.5 star property
9.6 out of 10, Exceptional, (53)
"This place is great. No hold deposit. Very very clean. Large condos. My family enjoyed themselves. I would highly recommend."
The price is NZ$588
includes taxes & fees
4 Jun - 5 Jun
Siena at Bella Collina
Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart
10.0 out of 10, Exceptional, (6)
"Very lovely house. Loved the golf cart, only used our SUV 4 times in the 2 wks we were there."
Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart
BRAND NEW Dog Friendly 2/2 w. Golf Cart - Close to Activities, Shopping, Dining!
10.0 out of 10, Exceptional, (36)
"This was our first time visiting the villages. We loved our place and had a great time. There was some food left in the pantry, coffee and other little things that made it feel at home. We loved the squares. Brownwood square is close enough with golf cart but, I would take care for Sumter lake."
BRAND NEW Dog Friendly 2/2 w. Golf Cart - Close to Activities, Shopping, Dining!
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4 BR / 3 BA orlando vacation pool home in Clermont, BBQ Grill, Free Wifi!!
7.6 out of 10, Good, (30)
"Everything were close to the house and the house is very beautiful I enjoyed my stayed."
4 BR / 3 BA orlando vacation pool home in Clermont, BBQ Grill, Free Wifi!!
BEAUTIFULLY Decorated 2/2 Sm Dog Friendly w/NEW GAS GOLF CART, BBQ & BICYCLES
9.6 out of 10, Exceptional, (10)
"This rental property was a great place to stay. Nicely located near activities."
BEAUTIFULLY Decorated 2/2 Sm Dog Friendly w/NEW GAS GOLF CART, BBQ & BICYCLES
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
10.0 out of 10, Exceptional, (65)
"Very nice and clean very close to all of the amenities that the villages offer"
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
Private 5 Bedroom Villa Near Disney, free WI-FI 10% OFF LONG TERM RENTALS
9.6 out of 10, Exceptional, (110)
"This house was beautiful and roomy. It was perfect for what we needed. It had nearby restaurants and grocery stores, and was not far from Orlando and Disney. It was an overall great stay."
Private 5 Bedroom Villa Near Disney, free WI-FI 10% OFF LONG TERM RENTALS
Orlando Area 4 BR/3 BA Villa - Pool, Spa, Game Room, Wi-Fi, Gated Community
10.0 out of 10, Exceptional, (102)
"This property was fantastic. It is equipped with everything that you can think of and spotless. Beds were super comfy. We had a very hot week so the pool was used every day and in the evening. The kids loved it. Check in was a breeze and location was out of the way but not too far from attractions. Any issue or questions were dealt with in the same day. The owners were great. Quiet neighborhood. Hoping to go again."
Orlando Area 4 BR/3 BA Villa - Pool, Spa, Game Room, Wi-Fi, Gated Community
Upgraded Orange Tree Home With Lots Of Extras!
9.6 out of 10, Exceptional, (79)
"Beautiful home spacious very quiet the location is great its 40 mins to the beach.Shopping and restaurants 2miles down the road. We loved the pool and ping pong tables.The pool was warm and the spa was wonderful.This home is fill with everything you need just add Family,Food and Fun! We will definitely be back soon!"
Upgraded Orange Tree Home With Lots Of Extras!
New 3/2 Patio Villa, BEST VALUE, Golf Cart Included!
9.8 out of 10, Exceptional, (6)
"Awesome place to stay, would definitely stay again very clean and loved the garage for keeping the motorcycles in"
New 3/2 Patio Villa, BEST VALUE, Golf Cart Included!
Patio Villa in Duval Village - *** Gas Golf Cart INCLUDED ***
9.8 out of 10, Exceptional, (67)
"Great rental property located in the center of The Villages. Comfortable furniture and bed. This is our sixth time visiting The Villages. We had a wonderful time golfing at the executive courses, dancing to the music at Brownstone and Sumter Landing squares. Enjoyed each day investigating so many activities. So much fun. We will be back."
Patio Villa in Duval Village - *** Gas Golf Cart INCLUDED ***
A perfect place to watch the Sunset
9.8 out of 10, Exceptional, (82)
"Very nice"
A perfect place to watch the Sunset
Clermont Home 12 Mi to Disney - Private Pool & Spa
9.8 out of 10, Exceptional, (29)
"Positive Aspects: 1. Safe and Family-Friendly Neighborhood: Located in a safe, quiet, and family-friendly neighbourhood. 2. Amenities: Proximity to food, grocery, and pharmacy locations was convenient. The games room and the Mickey Mouse room were great. Night lights in the Mickey room were appreciated. 3. Layout and Accessibility: Loved the bungalow layout and the access to the bathroom right from the pool deck. 4. Well-Equipped Kitchen: The kitchen was spacious and easy to cook in. Newer BBQ...
Clermont Home 12 Mi to Disney - Private Pool & Spa
Upto 45 Guests Sleep At This Unique Private Island 62 Acre Estate!
10.0 out of 10, Exceptional, (21)
"Great place with wonderful ownership and the most helpful staff. Definitely a place everyone should stay!!!"
Upto 45 Guests Sleep At This Unique Private Island 62 Acre Estate!
☀️Waterfront Villa on Quiet Cul-De-Sac–Beautiful, Spacious & Private, Games Rm🐠
9.8 out of 10, Exceptional, (191)
"Amazing property......very well appointed. The pool was a very big part of our stay. We all liked the location very much! This will be ado over for sure!!!!!"
☀️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
9.8 out of 10, Exceptional, (114)
"This was the perfect house for our family. We celebrated our two grandchildren's birthdays, 4 & 7. They thoroughly enjoyed the pool and had a fantastic time at Magic Kingdom and Animal Kingdom."
AWESOME HOUSE 5 bed/4 bath, south facing pool with spa & games room
Clermont Vacation Rental w/ Pool: 11 Mi to Disney
9.4 out of 10, Exceptional, (14)
"The house was in a beautiful community and was very clean and organized. We enjoyed the pool and jacuzzi along with the games in the game room. Would stay here again!"
Clermont Vacation Rental w/ Pool: 11 Mi to Disney
Clermont Villa w/ Lanai ~ 12 Miles to Disney!
9.8 out of 10, Exceptional, (18)
"Clean and comfortable 4 bedroom with plenty of space to relax. The kitchen has everything you need to feed them family and Publix is tight around the corner. The pool was a great addition to our vacation!"
Clermont Villa w/ Lanai ~ 12 Miles to Disney!
Private 3Bed/3Bath Heated Pool Outdoor Entertainment
10.0 out of 10, Exceptional, (2)
"This house was the perfect place for my family and I to stay in while visiting family in Zephyrhills! It can be a bit tricky getting out of the driveway since this house sits on a busier road, but it’s completely doable. The pool in the back was just icing on the cake! My kids enjoyed it immensely! The entire pool area is enclosed in a screened porch making it so nice to enjoy in the evenings. We will definitely look to stay here again!"
Private 3Bed/3Bath Heated Pool Outdoor Entertainment
Luxury and Comfort with game room
9.2 out of 10, Wonderful, (14)
"For this stay it was my mom, dad, fiance and my dog. We all absolutely loved this home and its amenities! The home was very clean and felt welcoming. We especially loved the beautiful open kitchen and patio/backyard area. My dog felt very comfortable as well and enjoyed roaming abiut in the home. The neighborhood is beautiful and very quiet. All of the neighbors were friendly and greeted you as you walked by. We went on walks every morning and evening and felt welcomed and safe. We absolutely...
The price is NZ$571
includes taxes & fees
30 May - 31 May
Luxury and Comfort with game room
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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.

Other types of properties in Webster you may be interested in

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel
4.0 star property
6.8 out of 10, (1005)
"Front desk host was very accommodating when I asked her to place me near pool with grandkids and asked for a late checkout. Nailed customer service skills. "
The price is NZ$268
includes taxes & fees
4 Jun - 5 Jun
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel
Spot X Hotel Tampa Bay by The Red Collection
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Rooms are small. Bed pillows small too. Room is clean and housekeeping is very helpful. A new washer and dryer in laundry room would be helpful. Dryer had some type of grease. Couldn’t use after washing clothes. Had to go to laundry mat. "
The price is NZ$170
includes taxes & fees
6 Jun - 7 Jun
Spot X Hotel Tampa Bay by The Red Collection
Brownwood Hotel & Spa
3.0 star property
9.6 out of 10, Exceptional, (1006)
"Beautiful hotel in every respect."
The price is NZ$277
includes taxes & fees
6 Jun - 7 Jun
Brownwood Hotel & Spa
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Webster holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Webster. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Webster. Seeing all the best attractions is bound to make you fall in love with Webster. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Webster short-term rentals, that won’t be hard to do.

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?

4 BR / 3 BA orlando vacation pool home in Clermont, BBQ Grill, Free Wifi!!: This holiday home rental outside Webster offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable 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.

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.

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