Deals on vacations and trips to Sumter County

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A lighthouse silhouetted against a sunset over a body of water.

The Villages

Vacations
The Villages
A river surrounded by dense forest with clear water and exposed tree roots.

Wildwood

Vacations
Wildwood

Sumter County flight + hotel vacation 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 $771, price is now $335 per person
$335
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $756, price is now $335 per person
$335
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $765, price is now $399 per person
$399
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
This hotel features an outdoor pool and a gym. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the hot tub and perks like free self parking.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,354, price is now $745 per person
$745
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Free water park access and an outdoor pool are featured at this smoke-free aparthotel. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,109, price is now $632 per person
$632
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Top Sumter County hotels deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
$100 nightly
The price is $107 total per night
$107 total
Jul 16 - Jul 17
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Hot Tub
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $112 total per night
$112 total
Jul 8 - Jul 9
Total with taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Spa
Hotel Eastport

Hotel Eastport

2 out of 5
7065 Beebe Court Wildwood FL
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $119 total per night
$119 total
Jul 8 - Jul 9
Total with taxes and fees
The hotel's outdoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free self parking and free WiFi. A coffee shop, luggage storage, and wedding services are also on offer.
Pool
Pet friendly
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
$91 nightly
The price is $97 total per night
$97 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED

The Villages FL
$197 nightly
The price is $209 total per night
$209 total
Jul 15 - Jul 16
Total with taxes and fees
An outdoor pool is featured at this vacation home, along with laundry facilities and barbecue grills.
Pool
Kitchen
Home2 Suites by Hilton Wildwood the Villages

Home2 Suites by Hilton Wildwood the Villages

3 out of 5
7555 PENROSE PLACE Wildwood FL
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $120 total per night
$120 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Pool
Breakfast included
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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 Sumter County attractions

Brownwood Paddock Square

You can enjoy retail therapy at Brownwood Paddock Square during your visit to Wildwood. Discover the live music and shops in this family-friendly area.
See properties

Photos of local treasures

Browse Sumter County vacation photos for more inspiration

Two blue boats docked at a pier with a lighthouse in the background.
A yellow golf cart on a paved road with palm trees and a body of water in the background.
A small boat with three birds on it, floating on calm water.
A row of golf carts parked on a street with trees and buildings in the background.
A bridge with the inscription "The Villages" under a clear blue sky.

Frequently asked questions

How much are vacation packages to Sumter County?
With Travelocity vacation packages, you can experience the sights and sounds of Sumter County for as little as $335. Hotels, flights and adventures — we've got it all. You'll save a bunch just by combining your bookings together. And with all that taken care of before you even go, you can sit back, relax and not worry about a thing.
Where can I get the best vacation package deals for Sumter County?
You can snap up unbeatable Sumter County package deals with Travelocity. Pick from as many as 400 partner airlines and 1,000,000 properties worldwide and turn those travel fantasies into reality.
Why should I book my Sumter County vacation bundle via Travelocity?
You'll not only enjoy huge savings, but you'll also have access to our 24/7 customer support, high-quality service and a Price Match Guarantee. Roam across the globe, discover hidden gems and create lifelong memories — we'll take care of the little details.
Will I save money on my Sumter County car rental if I book it with my hotel or flight?
Combining your bookings into a Sumter County vacation package will save you a handsome sum. Book a car and flight; a hotel, flight and car; or a car and hotel. There's no better way to discover the greater Sumter County area than from behind the wheel of your own rental car. You can also add experiences and activities to your Travelocity package.
Which airport is best for Sumter County?
You'll find three main hubs for anyone jetting to and from Sumter County — Orlando Intl. Airport (MCO), Tampa Intl. Airport (TPA) and Orlando Sanford Intl. Airport (SFB).
What is there to do in Sumter County?
Sumter County is overflowing with wonderful photo opportunities, however Nancy Lopez Legacy Golf & Country Club and Webster Westside Flea Market are right up there with the very best.

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