Book Exclusive Sumter County Vacation Packages

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

The Villages

Vacations
The Villages

Sumter County 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 $1,534, price is now CA $943 per person
CA $943
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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.
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was CA $2,076, price is now CA $1,290 per person
CA $1,290
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Kia Center and Camping World Stadium are located nearby.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,513, price is now CA $943 per person
CA $943
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. 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.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,720, price is now CA $1,727 per person
CA $1,727
per person
Sep 6 - Sep 12
found 13 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) 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.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,750, price is now CA $1,134 per person
CA $1,134
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
Book a stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orange County Convention Center and Aquatica are located nearby.

Top Sumter County 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 $149 per night
CA $149
CA $160 total
Jul 8 - Jul 9
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 The Villages Market Square and Brownwood Paddock Square are located nearby.
Pool
Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is CA $142 per night
CA $142
CA $152 total
Jul 27 - Jul 28
includes taxes & fees
Book a stay at this business-friendly hotel in The Villages. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Villages Market Square and Cane Garden Country Club are located nearby.
Pool
Hot tub
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 $156 per night
CA $156
CA $166 total
Jul 27 - Jul 28
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.
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
The price is CA $129 per night
CA $129
CA $138 total
Jul 19 - Jul 20
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 Okahumpka Park are located nearby.
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
The price is CA $70 per night
CA $70
CA $297 total
Jul 15 - Jul 16
includes taxes & fees
Stay at this vacation home in The Villages. Enjoy free WiFi, laundry facilities, and tennis courts. Popular attractions The Villages Market Square and Glenview Champions Country Club are located nearby.
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
The price is CA $160 per night
CA $160
CA $171 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Wildwood. Enjoy free breakfast, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Brownwood Paddock Square and Cane Garden Country Club are located nearby.
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 CA $943. 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.