Tall Trees Vacations from $214

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

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

Your Tall Trees Vacation

Take the stress and hassle out of organizing your next escape with a Tall Trees vacation package. Immerse yourself in the sights and sounds of this unique neighborhood and enjoy everything it has to offer. Start your trip to Tall Trees by checking out nearby attractions such as The Villages Market Square, Cane Garden Country Club and Glenview Champions Country Club. Stop dreaming and start doing. When you're ready to book your next vacation to Tall Trees, Expedia will help you get there.

The Latest Tall Trees Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

3.5 out of 5
Vilano Beach
Save 100% on your flight
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (543 reviews)
Nice Beach across the road, Very nice staff!

Reviewed on Jul 6, 2025

ette hotel

ette hotel

5 out of 5
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
very friendly helpful staff. nice area with many restaurants and grocery stores around. clean rooms. elegant hotel

Reviewed on Jul 4, 2025

Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (354 reviews)
Nice place. Kids had a good time. Not encouraged to go there if you are a minority. You wont feel welcomed. The staff is great, but the type of people that go there arent really folks that likely share the same interests as you do. There are Confederate flags all over; etc. Hotel rooms are no bueno, old. IF you want something nice, you need to spend the money glamping or have your own trailer.

Reviewed on Jun 24, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
per person
Sep 29 - Oct 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
7.8/10 Good! (1,649 reviews)
It took a very long time for them to come see about why the microwave wasn’t working in the room along with the remote control

Reviewed on Jul 13, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,274 reviews)
Location very convenient

Reviewed on Jul 13, 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
4.5/5(30 area reviews)

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

The Waterfront Inn
The Waterfront Inn
3 out of 5
1105 Lake Shore Drive, The Villages, FL
$139 nightly
The price is $149 total per night from Jul 15 to Jul 16
$149 total
Jul 15 - Jul 16
Total includes taxes and fees
9/10 Wonderful! (1,177 reviews)
"Our stay was just overnight but The Villages area is very nice. The Inn was very nice as well. Very quiet area where you felt safe taking a walk to go eat. Parking was super easy and plentiful. The A/C unit is top notch. I deducted 1* due to bed being a little to firm for me."

Reviewed on Jul 12, 2025

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
$119 nightly
The price is $133 total per night from Aug 10 to Aug 11
$133 total
Aug 10 - Aug 11
Total includes taxes and fees
8.4/10 Very Good! (1,001 reviews)
"Great place to stay."

Reviewed on Jul 2, 2025

Hilton Ocala
Brownwood Hotel & Spa
Brownwood Hotel & Spa
3 out of 5
3003 Brownwood Blvd, Wildwood, FL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $154 total per night from Jul 20 to Jul 21
$154 total
Jul 20 - Jul 21
Total includes taxes and fees
9.6/10 Exceptional! (1,011 reviews)
"As always: this hotel was excellent. The people, rooms, facilities, pool, and restaurant are all fantastic."

Reviewed on Jul 10, 2025

Brownwood Hotel & Spa
See all 2,049 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

Kid Friendly Vacations

Kid Friendly Vacations

Discover the most popular places to visit in Tall Trees

The Villages Market Square

4.5/5(174 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

Nancy Lopez Legacy Golf & Country Club

Enjoy a round of golf in The Villages at Nancy Lopez Legacy Golf & Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Nancy Lopez Legacy Golf & Country Club

Glenview Champions Country Club

Enjoy a round of golf in The Villages at Glenview Champions Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Glenview Champions Country Club

Things to do

King William, a Gypsy Vanner Horse Stallion

Gypsy Gold Horse Farm Tour

$55
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.