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.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was CA $1,155, price is now CA $660 per person
CA $660
per person
Nov 11 - Nov 15
just found
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springsâ„¢ are located nearby.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was CA $2,749, price is now CA $1,483 per person
CA $1,483
per person
Nov 22 - Nov 27
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) 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.
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 CA $3,176, price is now CA $1,785 per person
CA $1,785
per person
Nov 29 - Dec 6
found 15 hours ago
Roundtrip flight included
Detroit (DTW) 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.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was CA $3,602, price is now CA $2,100 per person
CA $2,100
per person
Nov 7 - Nov 14
found 20 hours 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 Bradenton Beach and Coquina Beach are located nearby.
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
Price was CA $1,395, price is now CA $846 per person
CA $846
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.

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 $145 per night
CA $145
CA $155 total
Oct 18 - Oct 19
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 $139 per night
CA $139
CA $148 total
Oct 22 - Oct 23
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 $118 per night
CA $118
CA $126 total
Oct 18 - Oct 19
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.
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 $141 per night
CA $141
CA $386 total
Oct 24 - Oct 25
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 $144 per night
CA $144
CA $154 total
Oct 11 - Oct 12
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.
Pool
Breakfast included
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 $203 per night
CA $203
CA $218 total
Oct 8 - Oct 9
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
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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 $660. 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.