Book Exclusive Webster Vacation Packages

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Webster flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,106, price is now CA $575 per person
CA $575
per person
Oct 13 - Oct 19
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,067, price is now CA $1,162 per person
CA $1,162
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
Book a stay at this beach aparthotel in Cocoa Beach. Enjoy free parking, a beach locale, and free water park access. Our guests praise the helpful staff in our reviews. Popular attractions Cocoa Beach and Jetty Park are located nearby.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,298, price is now CA $1,379 per person
CA $1,379
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was CA $1,878, price is now CA $1,155 per person
CA $1,155
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,964, price is now CA $1,897 per person
CA $1,897
per person
Sep 10 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and Bean Point Beach are located nearby.

Top Webster hotels deals

Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Free cancellation
Reserve now, pay when you stay
The price is CA $162 per night
CA $162
CA $173 total
Aug 25 - Aug 26
includes taxes & fees
Book a stay at this spa hotel in Wildwood. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Brownwood Paddock Square and Lake Okahumpka Park are located nearby.
Pool
Spa
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
5700 Saddlebrook Way Wesley Chapel FL
Free cancellation
Reserve now, pay when you stay
The price is CA $182 per night
CA $182
CA $248 total
Aug 12 - Aug 13
includes taxes & fees
Book a stay at this golf resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.
SPOT X Hotel Tampa - Wesley Chapel by The Red Collection

SPOT X Hotel Tampa - Wesley Chapel by The Red Collection

3 out of 5
5703 Oakley Blvd Wesley Chapel FL
Get rates
Book a stay at this business-friendly hotel in Wesley Chapel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions KRATE Shopping Center and The Grove at Wesley Chapel are located nearby.
Days Inn by Wyndham Brooksville/Dade City

Days Inn by Wyndham Brooksville/Dade City

2 out of 5
6320 Windmere Rd Brooksville FL
Free cancellation
Reserve now, pay when you stay
The price is CA $84 per night
CA $84
CA $94 total
Sep 6 - Sep 7
includes taxes & fees
Book a stay at this golf motel in Brooksville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sherman Hills Golf & Country Club and Withlacoochee Trail State Park are located nearby.
Hotel Eastport

Hotel Eastport

2 out of 5
7065 Beebe Court Wildwood FL
Free cancellation
Reserve now, pay when you stay
The price is CA $166 per night
CA $166
CA $177 total
Aug 9 - Aug 10
includes taxes & fees
Book a stay at this golf hotel in Wildwood. Enjoy free WiFi, free parking, and 2 bars/lounges. Popular attractions Shallow Creek Country Club and Continental Country Club are located nearby.
Holiday Inn Express & Suites Wildwood The Villages by IHG

Holiday Inn Express & Suites Wildwood The Villages by IHG

3.5 out of 5
928 East State Road 44 Wildwood FL
Free cancellation
The price is CA $123 per night
CA $123
CA $132 total
Sep 6 - Sep 7
includes taxes & fees
Book a stay at this business-friendly hotel in Wildwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brownwood Paddock Square and Lake Panasoffkee are located nearby.
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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.

Stay near popular Webster attractions

Webster Westside Flea Market

8.4/10 (40 reviews)
You can do some window-shopping at Webster Westside Flea Market during your trip to Webster. You can enjoy the coffeehouses while in the area.
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Webster Vacations

We get it, geography isn't everyone's specialty. If you're not sure where Webster sits on a map, you'd be wise to investigate its location before you jet off!

You'll find it 11 miles (18 kilometers) from Mascotte and 13 miles (21 kilometers) from Dade City.

Ready to rub shoulders with the locals? 800 people call this part of Florida home.

Places to visit in Webster

Slip on your khakis and find your lucky putter. If you'd love to get outside for an afternoon on the green, secure a tee time at Sherman Hills Golf & Country Club. Need more options? Time spent in nature is proven to enhance both your physical and spiritual state of being. Spend time at Withlacoochee Trail State Park and experience the benefits of reconnecting with our natural world. That's not all there is to do here. An excellent way to really experience an area's culture is to venture to its lively marketplaces. Browse through the products and shop like a local at Webster Westside Flea Market.

Where do you fly into for Webster?

There's no better feeling than finally hitting the tarmac in a new place. If you're going to Webster, there's a good chance you'll be flying into Orlando International Airport (MCO). It's 45 miles (72 kilometers) to the east of the main streets. Collect your luggage and get set to kick-start your vacation!

Frequently asked questions

How much are vacation packages to Webster?
Enjoy an unforgettable travel experience in Webster with a vacation package starting from as low as CA $575. Organizing your tours, hotels and flights with Travelocity is so simple. And even better, our great deals will leave you with more cash in your pocket for fun, fun, fun!
Where can I get the best vacation package deals for Webster?
For an amazing package deal to Webster, book with Travelocity. Choose from 400 partner airlines and 1,000,000 properties across the globe to create your ultimate adventure — it couldn't be simpler.
Why should I purchase my Webster vacation package via Travelocity?
Whether you're searching for the ultimate unplugged vacation or you crave the fun and excitement of the big smoke, booking everything with Travelocity saves you time, money and hassle. No need to sift through hundreds of websites looking for the best deal — our Price Match Guarantee ensures you'll always get the lowest price, and our professional customer service experts are available 24/7 should you need anything at all.
Can I save on my Webster car rental if I combine it with my hotel or flight?
With a Webster vacation package, you can bundle your flight, hotel and car bookings and save a whole lot. If you can't wait to uncover the best of this wonderful location, why not check out Universal Studios Florida? This top sight is 56 kilometers from Webster. With your own wheels, you'll be there in a flash.
Which airport is best for Webster?
Orlando Intl. Airport (MCO) is popular. It's located approximately 72 kilometers east of Webster. Other options worth considering are Tampa Intl. Airport (TPA) (88 kilometers away from central Webster) and Orlando Sanford Intl. Airport (SFB) (80 kilometers away from central Webster).
What is there to do in Webster?
Webster Westside Flea Market should be at the top of your itinerary. Once you've crossed off this well-known attraction, simply roam the streets of Webster and discover what makes this wonderful destination tick.
Where should I stay when visiting Webster?
If you're looking for somewhere to base yourself, consider the River Daze Cabin - A cozy cabin right on the river. It's the top pick for many travelers.

Photos of local treasures

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