Book Exclusive Sumter County Vacation Packages

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Search vacation packages deals in Sumter County's top destinations

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 Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,471, price is now CA $808 per person
CA $808
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $2,455, price is now CA $1,141 per person
CA $1,141
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye are located nearby.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,263, price is now CA $1,400 per person
CA $1,400
per person
Oct 15 - Oct 19
found 11 hours ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
Book a stay at this family-friendly aparthotel in Cocoa Beach. Enjoy free parking, free water park access, and a lazy river. Our guests praise the helpful staff in our reviews. Popular attractions Cocoa Beach and Ron Jon Surf Shop are located nearby.
WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Price was CA $1,688, price is now CA $1,048 per person
CA $1,048
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Old Town and Disney Springsâ„¢ are located nearby.
CW Hotel

CW Hotel

4 out of 5
Price was CA $2,187, price is now CA $1,370 per person
CA $1,370
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

Top Sumter County hotels deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is CA $146 per night
CA $146
CA $156 total
Sep 3 - Sep 4
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 Lake Sumter are located nearby.
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
The price is CA $153 per night
CA $153
CA $164 total
Sep 1 - Sep 2
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
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 $117 per night
CA $117
CA $125 total
Sep 20 - Sep 21
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.
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 $163 per night
CA $163
CA $174 total
Sep 9 - Sep 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.
Pool
Pet-friendly
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
The price is CA $109 per night
CA $109
CA $117 total
Sep 21 - Sep 22
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
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 $129 per night
CA $129
CA $138 total
Aug 30 - Aug 31
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 The Villages Market Square and Brownwood Paddock Square 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 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 $808. 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.