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 Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $588, price is now $328 per person
$328
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $792, price is now $403 per person
$403
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $620, price is now $339 per person
$339
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,526, price is now $847 per person
$847
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.
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 $619, price is now $348 per person
$348
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.

Top Sumter County hotels deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
$99 nightly
The price is $106 total per night
$106 total
Oct 7 - Oct 8
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
Oct 6 - Oct 7
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
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
$79 nightly
The price is $85 total per night
$85 total
Oct 18 - Oct 19
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.
Pool
Breakfast included
Comfort Inn & Suites Wildwood - The Villages

Comfort Inn & Suites Wildwood - The Villages

2.5 out of 5
1224 S Main St Wildwood FL
Free Cancellation
$75 nightly
The price is $80 total per night
$80 total
Oct 11 - Oct 12
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. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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
$216 nightly
The price is $229 total per night
$229 total
Sep 27 - Sep 28
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
$94 nightly
The price is $100 total per night
$100 total
Sep 28 - Sep 29
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 $328. 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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