Tall Trees Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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 Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $920, price is now CA $527 per person
CA $527
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8/10 Very Good! (1,675 reviews)
Enjoyed every moment,front desk was very friendly and sweet

Reviewed on Sep. 1, 2025

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was CA $1,611, price is now CA $584 per person
CA $584
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.2/10 Very Good! (5,167 reviews)
Nice to stay with family and breakfast was perfect

Reviewed on Sep. 1, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,297, price is now CA $690 per person
CA $690
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8/10 Very Good! (1,346 reviews)
First off the front desk needs retraining they gave us the completly incorrect room. Second the correct room the ceiling leaked. Third room was not properly cleaned the pull out sofa had visible crumbs and the ac unit was inoperable. The final upgraded room was extremely excellent.

Reviewed on Sep. 1, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $1,786, price is now CA $974 per person
CA $974
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (1,008 reviews)
Being able to text the front desk for my needs was very helpful! Staff was friendly and the Universal shuttles were convenient.

Reviewed on Aug. 30, 2025

ette hotel

ette hotel

5 out of 5
Price was CA $2,248, price is now CA $1,275 per person
CA $1,275
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on Aug. 11, 2025

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
Default Image

Lake Sumter Landing

1 out of top 10 points of interest in this area

Though Lake Sumter Landing might not have many top sights, you can venture to the surrounding area to see attractions like The Villages Market Square and Spanish Springs Town Square.

Find hotels in Lake Sumter Landing

Tall Trees Hotel Deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive, The Villages, FL
The price is CA $160 per night from Sep 4 to Sep 5
CA $160
CA $171 total
Sep 4 - Sep 5
includes taxes & fees
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 $166 per night from Oct 1 to Oct 2
CA $166
CA $177 total
Oct 1 - Oct 2
includes taxes & fees
Brownwood Hotel & 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
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Sep 7 to Sep 8
CA $116
CA $124 total
Sep 7 - Sep 8
includes taxes & fees
Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,095 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 $527. 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.

Discover the most popular places to visit in Tall Trees

The Villages Market Square

You can enjoy retail therapy at The Villages Market Square during your visit to The Villages. Wander the lakeside in this quaint area.

The Villages Market Square

Things to do

King William, a Gypsy Vanner Horse Stallion

Gypsy Gold Horse Farm Tour

CA $76
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.