Tall Trees Vacations from $253

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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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,119, price is now $253 per person
$253
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,145 reviews)
I never leave reviews, but this place deserves one. It was so clean and employees were so nice. Breakfast was good and a breeze, and lasted all the way til 930 which most places do not do. I’ll definitely be staying here again next time.

Reviewed on Dec 11, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,423, price is now $536 per person
$536
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The outside of the building could use some tlc but inside was clean and updated. Staff was attentive, polite, & helpful. Breakfast was surprisingly better than I anticipated with hot options outside of the traditional continental options. Furniture around pool was pressure washed every morning and plentiful. There are no seating options for the beach however we would definitely stay here again.

Reviewed on Nov 30, 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $954, price is now $383 per person
$383
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (2,232 reviews)
The room was spotless, the staff was wonderful and the location was so convenient. We had a toddler with us so being attached to the mall made it so easy for us to spend the evening outside the hotel room but not having to drive around either. The hotel was so nice, if we find ourselves back in Orlando we will stay here again

Reviewed on Dec 11, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,195, price is now $503 per person
$503
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,085 reviews)
If you want dirty towels with previous guests stains and hair on it then this is the place for you.

Reviewed on Dec 9, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $950, price is now $404 per person
$404
per person
Feb 17 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
La habitacion muy buena y limpia expaciosa recomendaria cambiar ollas y sartenes estan muy viejos y quemados

Reviewed on Dec 4, 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
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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 Dec 14 to Dec 15
$149 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (1,276 reviews)
Great place

Reviewed on Dec 7, 2025

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
$149 nightly
The price is $159 total per night from Jan 1 to Jan 2
$159 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.6/10 Exceptional! (1,071 reviews)
Front desk check in staff very friendly, room spotless and comfortable.

Reviewed on Dec 8, 2025

Brownwood Hotel & Spa
Hilton Ocala

Hilton Ocala

3.5 out of 5
3600 Sw 36th Ave Ocala FL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Dec 21 to Dec 22
$109 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Everything was great

Reviewed on Dec 7, 2025

Hilton Ocala
See all 2,227 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.