Tall Trees Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Tall Trees

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was CA $1,072, price is now CA $589 per person
CA $589
per person
Nov 25 - Nov 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very good! (7,259 reviews)
The staff and hotel were excellent. The only hassle was parking, but my concerns were quickly addressed by staff.

Reviewed on Oct 26, 2026

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was CA $1,913, price is now CA $963 per person
CA $963
per person
Jan 1 - Jan 8
found 8 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9/10 Wonderful! (4,064 reviews)
It was a clean and quaint little spot. It had all the things I needed for a restful stay.

Reviewed on Oct 26, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was CA $4,404, price is now CA $2,224 per person
CA $2,224
per person
Dec 28 - Jan 4
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (565 reviews)

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 $3,359, price is now CA $1,881 per person
CA $1,881
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was CA $2,194, price is now CA $1,250 per person
CA $1,250
per person
Jan 1 - Jan 8
found 8 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.6/10 Exceptional! (1,234 reviews)

Where to stay in Tall Trees

Find the best Tall Trees areas and neighborhoods for the activities you enjoy most. Learn more about Tall Trees
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

While visiting Lake Sumter Landing, you might make a stop by sights like The Villages Market Square and Lake Sumter.

Find hotels in Lake Sumter Landing

Tall Trees Hotel Deals

Location is perfect, Close to Sumter Landing, shopping and Golf Cart included,

Location is perfect, Close to Sumter Landing, shopping and Golf Cart included,

The Villages FL
9.6/10 Exceptional! (55 reviews)
"Had a great stay. Would definitely rebook! Very clean and comphy"

Reviewed on Oct 26, 2026

Get rates
Location is perfect, Close to Sumter Landing, shopping and Golf Cart included,
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is CA $158 per night from Nov 1 to Nov 2
CA $158
CA $169 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (1,548 reviews)
"Very comfortable and clean, plus a beautiful location overlooking the lake. Town Square restaurants and stires were an easy 2-3 block walk. Plenty of hotel parking. Great Happy Hour and lots of menu choices for lunch and dinner. ( no Breakfast) I would stay there again and again."

Reviewed on Oct 26, 2026

The Waterfront Inn
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 CA $194 per night from Nov 12 to Nov 13
CA $194
CA $207 total
Nov 12 - Nov 13
includes taxes & fees
Brownwood Hotel & Spa
See all 2,319 properties in Tall Trees
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Tall Trees vacation package cost?
We make it easy to see the world, with Tall Trees packages starting from as little as CA $589. You'll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate escape, why not add a few tours and experiences to your travel itinerary?
How do I get a cheap travel package to Tall Trees?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got it all. Select the combination that suits your style and see your savings grow. Of course, a travel package is never a one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 properties across the globe, which lets you customize your Tall Trees adventure.
Where should I stay in Tall Trees?
With so much to explore in Tall Trees, we recommend you book a room in a hotel near its attractions. The Villages Market Square, Cane Garden Country Club and Glenview Champions Country Club are some top ones to add to your itinerary.
What are the top hotels in Tall Trees?
Lock in a room at Charming 3/2 Home Close To Shopping W. It's one of the neighborhood's most sought-after properties. Another top-rated option in Tall Trees is Beautiful 3/2 Home Close To Shopping W.
How far in advance should I book my Tall Trees vacation?
Be rewarded with the widest variety at the cheapest prices by booking your vacation to Tall Trees nice and early. Airlines generally publish flight tickets anywhere up to a year before departure, so secure your spot as soon as you can. Having said that, Expedia is dedicated to providing you with the best bargains around, so there's never a bad time to book your dream vacation!
What does an Expedia Tall Trees travel package include?
Select from any combination of flights, rental cars and hotels. Once you've made your booking, you can add experiences and tours. Want to pick your fare class? That's easily done too. The choice is all yours when it comes to crafting your ideal Tall Trees escape.
What should I know before booking a Tall Trees travel package?
Bundling your bookings into a Tall Trees vacation package is the most convenient way to organize your trip. Not only that, you'll get great discounts when you combine your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Tall Trees Expedia vacation package?
You can, and with more than 550 airlines to choose from worldwide, you have loads of choice. Search the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Tall Trees vacation package?
We get it — life sometimes gets in the way of your plans. If you've locked in a Tall Trees vacation package and need to change or cancel it, we're here to help. We suggest browsing our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to cancel or amend your itinerary for free. If it's been longer than 24 hours, your hotel, airline or car rental company may impose a charge.

Things to do

Gypsy Gold Horse Farm Tour

Gypsy Gold Horse Farm Tour

CA $78
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.