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.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was CA $1,165, price is now CA $743 per person
CA $743
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (3,629 reviews)
This is a nice hotel. I wanted a place that was quiet. The staff was great from the time I checked in until I checked out. I was very impressed at how nice the place looked nad was. Everything was where it was supposed to be. . I was impressed with the place nad I know if given the chance I would go back.

Reviewed on Jun 21, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,736, price is now CA $1,060 per person
CA $1,060
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (6,626 reviews)
We had a wonderful stay at Westgate Resort. The room was clean, comfortable, and well-maintained. The staff was friendly and helpful throughout our visit, and the property itself was beautiful and family-friendly. We especially enjoyed the amenities and overall atmosphere. The only suggestions I would make are that guests should be informed more clearly at check-in that access to the water park and certain resort amenities requires an additional fee, as this was not fully explained beforehand. Also, the $50 deposit refund has taken longer than expected to be returned. Overall, despite these minor inconveniences, we had a great experience and would definitely stay here again. The resort offers excellent accommodations and a pleasant environment for families and travelers alike.

Reviewed on Jun 20, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,844, price is now CA $1,765 per person
CA $1,765
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (550 reviews)
Esta bien Accesible a todas las amenidades, incluyendo el área de la playa,Solo que es un poco caro el precio por noche, por lo demás todo muy bien.

Reviewed on May 25, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,917, price is now CA $1,927 per person
CA $1,927
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,009 reviews)
The cottage was wonderful. Stocked with everything you need just bring your food, drink and toilet paper! The cottage we stayed at was a perfect location just 5 minute walk to the amazing pool complex. The resort is great. Planning on going back soon.

Reviewed on Jun 20, 2026

Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Price was CA $1,376, price is now CA $930 per person
CA $930
per person
Aug 30 - Sep 6
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (1,881 reviews)
We live in Cocoa, in DB for medical apptmts. Great view from oceanfront suite. We did not use any amenities - pool was busy. The staff was helpful. One young man from Jamaica (he was new) went above and beyond to find a small missing tote bag. The food at Oasis (outdoor bar/grill at Fountain Hotel, next door, short walk) was very good. We ate there a few times, good every visit.

Reviewed on Jun 21, 2026

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
Lake Sumter Landing

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 Cane Garden Country Club.

Find hotels in Lake Sumter Landing

Tall Trees Hotel Deals

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 $153 per night from Jun 29 to Jun 30
CA $153
CA $164 total
Jun 29 - Jun 30
includes taxes & fees
9.8/10 Exceptional! (1,220 reviews)
"Beautiful hotel - we enjoyed our stay, nice spacious room and bathroom, nice pool and convenient location in The Villages with lots of places to eat - definitely stay here again when visiting this area !"

Reviewed on Jun 18, 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is CA $139 per night from Jun 29 to Jun 30
CA $139
CA $148 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,427 reviews)
"A very nice hotel with lots of amenities. Food and entertainment within walking distance. Super friendly and helpful staff."

Reviewed on Jun 20, 2026

The Waterfront Inn
Hilton Ocala

Hilton Ocala

3.5 out of 5
3600 Sw 36th Ave Ocala FL
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jun 22 to Jun 23
CA $155
CA $173 total
Jun 22 - Jun 23
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Very nice inside and out! Cool bar area. And the kids loved feeding the horses out back"

Reviewed on Jun 19, 2026

Hilton Ocala
See all 2,250 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 $743. 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

4.5/5(2 reviews)

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

Gypsy Gold Horse Farm Tour

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.