Winifred Holidays from £666

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Your Winifred Holiday

Planning your next break just got a whole lot simpler with a holiday package to Winifred. Experience the very best this neighbourhood has to offer while making nice memories you'll remember for years. Can't wait to do some sightseeing during your trip to Winifred? Be sure to stop by nearby attractions such as The Villages Market Square, Cane Garden Country Club and Glenview Champions Country Club. Expedia will help you turn your dream Winifred holiday into reality, no matter your travel plans or budget.

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

Palazzo Lakeside Hotel

3 out of 5
Price was £1,333, price is now £666 per person
£666
per person
29 Aug - 5 Sept
found 22 hours ago
Return flight included
London (LON) to Orlando (MCO)
8.2/10 Very good! (5,209 reviews)
staff should be better in speaking english

Reviewed on 14 Jul 2026

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 £2,326, price is now £1,305 per person
£1,305
per person
26 Aug - 2 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)
Overall the stay was fine. When booking, it’d be helpful if it’s made clear that most of the cottages are upwards of a mile or more away from the main resort area. This makes trips to use the pool and water park vehicle trips coupled with finding parking. Also, what set the trip off in the worst possible way was the fact that immediately after checking in, you are literally herded to a kiosk where they begin a high pressure timeshare pitch complete with “what time can we pick you up for your meeting tomorrow?” We just flew in, haven’t seen the resort yet, have starving kids, and already have to fight off this nonsense. A great way to abuse your patrons and ensure they will have a bad experience immediately upon arrival. That alone was almost enough to make someone not want to return.

Reviewed on 14 Jul 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was £1,485, price is now £958 per person
£958
per person
3 Oct - 10 Oct
found 1 day ago
Return flight included
London (LON) to Orlando (MCO)
9.6/10 Exceptional! (1,129 reviews)
Everything about this hotel was immaculate from the staff to the restaurant to the location and of course the rooms and the bathroom are well kept very update to date. I’ll give them a 10 out of 10. Definitely recommend this hotel.

Reviewed on 10 Jul 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was £1,196, price is now £834 per person
£834
per person
26 Aug - 2 Sept
found 6 hours ago
Return direct flight included
Edinburgh (EDI) to Orlando (MCO)
8.4/10 Very good! (6,621 reviews)
Te best response is I’m willing to come back

Reviewed on 14 Jul 2026

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was £930, price is now £671 per person
£671
per person
3 Oct - 10 Oct
found 1 day ago
Return flight included
London (LON) to Orlando (MCO)
9/10 Wonderful! (3,664 reviews)
I got there a little early and they were able to get me right into my room. The room was perfectly clean! The bed was very comfortable and the A/C was amazing (it was like 100° outside) and kept my room nice and cool. The staff was very friendly and helpful. I was 100% recommend this hotel to anyone traveling in that area

Reviewed on 14 Jul 2026

Where to stay in Winifred

Find the best Winifred areas and neighborhoods for the activities you enjoy most. Learn more about Winifred
A yellow golf cart on a paved road with palm trees and a body of water in the background.

Lake Sumter Landing

1 out of top 10 points of interest in this area

If you're spending some time in Lake Sumter Landing, The Villages Market Square and Lake Sumter are top sights worth seeing.

Find hotels in Lake Sumter Landing

Top hotels in Winifred

FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!

FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!

The Villages FL
10/10 Exceptional! (62 reviews)
"Great communication and great place"

Reviewed on 11 Jul 2026

Get rates
FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
The price is £84 per night from 21 Jul to 22 Jul
£84
21 Jul - 22 Jul
includes taxes & fees
9.8/10 Exceptional! (1,281 reviews)
"This hotel was perfect for our stay with our dog. Everyone was so nice and helpful."

Reviewed on 13 Jul 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is £81 per night from 12 Aug to 13 Aug
£81
12 Aug - 13 Aug
includes taxes & fees
9.2/10 Wonderful! (1,450 reviews)
"THE STAFF WERE VERY FRIENDLY AND THE LOCATION IS GREAT!"

Reviewed on 14 Jul 2026

The Waterfront Inn
See all 2,268 properties in Winifred
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Winifred travel package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Winifred from just £666. And the more you bundle, the more cash you save. Your dream escape has never been so affordable.
If I'm not able to travel, can I cancel my Winifred travel package?
Don't worry if you're rethinking your Winifred travel package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We know life can throw the occasional spanner in the works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to Winifred?
Crafting your own Winifred travel package with Expedia is a simple way to save. We offer access to over 550 partner airlines and 1,000,000 hotels throughout the world. With such a huge range to pick from, you'll have no hassles pulling together your perfect getaway.
Does Expedia offer Book Now, Pay Later Winifred holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply click on the payment plan that suits best during checkout and take away the stress of budgeting for your next trip. Be sure to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's convenient monthly instalment plans. If making bite-sized repayments each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip in multiple transactions.
  • Low deposit holidays: When you see an amazing deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock it in.

Where should I stay in Winifred?
Stay where the action is. Many people favor hotels within easy reach of popular sights, such as The Villages Market Square, Cane Garden Country Club and Glenview Champions Country Club.
What are the top hotels in Winifred?
Reserve a room at The Waterfront Inn. It's one of the area's most popular properties. Another well-known option in Winifred is Hampton Inn & Suites Lady Lake/The Villages.
How far in advance should I book my Winifred holiday?
Browse Expedia to compare international flights ASAP. You can generally purchase a seat up to 12 months in advance. If you don't see your preferred air carrier, or you have to book last minute, don't stress. Cheap fares to Winifred sometimes occur just weeks before departure.
What does an Expedia Winifred travel package include?
It's up to you! You can select from a variety of Winifred bundles, such as a flight, hotel and rental car. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like activities and experiences. Whatever your dream Winifred holiday looks like, you're sure to save!
What should I know before booking a Winifred travel package?
A travel package can be tailored to your budget and is a terrific way to stretch your hard-earned dollars. What you include is your call. Rental cars, hotels and flights — come up with a combination that suits your plans.
Can I choose my airline with a Winifred Expedia travel package?
Yes — that's one of the best things about an Expedia package. You can pick and choose your flights, hotels and more. We have more than 550 airline partners around the world, so you have options galore when putting together your Winifred escape.

Things to do

Gypsy Gold Horse Farm Tour

Gypsy Gold Horse Farm Tour

£41
per adult
100% of travellers recommend
Gypsy Gold Horse Farm Tour
See all activities in The Villages

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.