Middleton Vacation Packages

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Top Middleton Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Seasons Florida Resort

CA $1,337

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Orlando (MCO)

9/10 Wonderful! (3,949 reviews)

Westgate Cocoa Beach Resort

Save 100% on your flight

CA $1,441

per person

Nov 15 - Nov 21

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Orlando (MCO)

8.6/10 Excellent! (565 reviews)

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

CA $1,495

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Orlando (MCO)

8.4/10 Very good! (7,160 reviews)

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

CA $1,596

per person

Dec 18 - Dec 23

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Orlando (MCO)

9.2/10 Wonderful! (1,003 reviews)

We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms. The staff at the main building were so helpful with our packages and printing documents for us. Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort. Overall, a great selection and would start again!

Reviewed on Sep 25, 2026

Florida Hotel & Conference Center in the Florida Mall

Save 100% on your flight

CA $1,538

per person

Dec 20 - Dec 27

found 10 hours ago

Roundtrip flight included

Halifax (YHZ) to Orlando (MCO)

9.2/10 Wonderful! (1,380 reviews)

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Middleton Hotel Deals

The Waterfront Inn

1105 Lake Shore Drive The Villages FL

CA $138

CA $148 total

Nov 2 - Nov 3

includes taxes & fees

9.4/10 Exceptional! (1,519 reviews)

"The Waterfront Inn is a beautiful property in a great location in The Villages. It is just a short walk to entertainment and restaurants in addition to having a restaurant and bar onsite. The room was really nice and clean. We enjoyed the heated pool and jacuzzi with a wonderful view. The staff were ..."

Reviewed on Oct 1, 2026

Brownwood Hotel & Spa

3003 Brownwood Blvd Wildwood FL

Fully refundableReserve now, pay when you stay

CA $140

CA $150 total

Oct 22 - Oct 23

includes taxes & fees

The Citrus on the Lake

199 W Ruby Street Tavares FL

Fully refundableReserve now, pay when you stay

CA $138

CA $153 total

Oct 28 - Oct 29

includes taxes & fees

See all 2,251 properties in Middleton

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.