Pleasant Street Vacation Packages

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Top Holiday Package Deals in Pleasant Street

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $782, price is now CA $459 per person
CA $459
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,346 reviews)
The property is very beautiful and they do a wonderful job keeping it clean. However, it's far too big for older visitors and there are no benches to rest while walking.

Reviewed on Aug. 26, 2025

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was CA $1,423, price is now CA $525 per person
CA $525
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.2/10 Very Good! (5,171 reviews)
It was very clean and comfortable! The staff were extremely friendly! The area around the property is really pretty!

Reviewed on Aug. 27, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $2,294, price is now CA $1,087 per person
CA $1,087
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (1,002 reviews)
We didn’t have keys to our room for over 24 hours

Reviewed on Aug. 28, 2025

ette hotel

ette hotel

5 out of 5
Price was CA $2,784, price is now CA $1,417 per person
CA $1,417
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on Aug. 11, 2025

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Price was CA $1,829, price is now CA $1,072 per person
CA $1,072
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.8/10 Excellent! (1,377 reviews)
Property was great! Wish we were able to stay longer

Reviewed on Aug. 27, 2025

Where to stay in Pleasant Street

Find the best Pleasant Street areas and neighborhoods for the activities you enjoy most. Learn more about Pleasant Street
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University Heights

While University Heights isn't home to many top sights, Ben Hill Griffin Stadium and Hippodrome State Theatre are some notable places to visit nearby.

Find hotels in University Heights

Pleasant Street Hotel Deals

Hotel Eleo at the University of Florida

Hotel Eleo at the University of Florida

3 out of 5
1514 Southwest 14th Street, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Aug 31 to Sep 1
CA $209
CA $235 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (1,261 reviews)
"Staff couldn’t be nicer and more accommodating!"

Reviewed on Aug. 21, 2025

Hotel Eleo at the University of Florida
Sleep Inn & Suites University/Shands

Sleep Inn & Suites University/Shands

2.5 out of 5
4110 SW 40th Boulevard, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Sep 7 to Sep 8
CA $104
CA $125 total
Sep 7 - Sep 8
includes taxes & fees
Sleep Inn & Suites University/Shands
DoubleTree by Hilton Gainesville

DoubleTree by Hilton Gainesville

4 out of 5
3726 Sw 40th Blvd, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Sep 7 to Sep 8
CA $120
CA $135 total
Sep 7 - Sep 8
includes taxes & fees
DoubleTree by Hilton Gainesville
See all 780 properties in Pleasant Street
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 Pleasant Street vacation package cost?
The cheapest Pleasant Street package is CA $459, so your dream escape can become a reality — without spending an arm and a leg. Bundle flights, hotels, car rentals and more to tailor a package that suits you.
How do I get a cheap travel package to Pleasant Street?
Find flights that suit your busy schedule, add a hotel room to your booking and watch the savings pile up with a Pleasant Street vacation package. It's that simple! From flights and hotels to rental cars and tours, Expedia makes traveling cheap and easy. And with over 550 partner airlines and 1,000,000 hotels across the globe to choose from, you won't be short of choice.
Where should I stay in Pleasant Street?
Make sightseeing easy by staying in a hotel just a stone's throw away from Pleasant Street's main attractions. University of Florida and Florida Museum of Natural History are two traveler favorites.
What are the top hotels in Pleasant Street?
If it's comfort and convenience you want, you can't beat Beautiful 7th Floor Condo In Gainesville. Spend your evenings relaxing here and your days checking out Pleasant Street's popular attractions.
How far in advance should I book my Pleasant Street vacation?
It's tricky picking the perfect time for airfares, but we generally say the earlier, the better. Many international journeys on Expedia become available up to a year in advance. If you can't book ahead, don't stress. Bargain prices occasionally appear within a few weeks of departure dates.
What does an Expedia Pleasant Street travel package include?
Travel packages include hotels, rental cars and flights, but you can mix and match them to create your dream Pleasant Street escape. You can also add on activities and experiences once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll get access to discounts you won't find anywhere else.
What should I know before booking a Pleasant Street travel package?
Get ready to save with an Expedia travel package. Combine your flights, rental cars and hotels and land fantastic discounts. Hotels aren't your only choice, though. Book with us and select from beachfront villas, chalets in the middle of mountains and everything in between!
Can I choose my airline with a Pleasant Street Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You're in charge! We have access to more than 550 partner airlines globally, so you have loads of choice when putting together your Pleasant Street adventure.
If I'm not able to travel, can I cancel my Pleasant Street vacation package?
Because we know life is full of surprises, the answer is yes. To learn more, check out our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in Pleasant Street

Shands at the University of Florida

4.5/5(2 reviews)

Though Shands at the University of Florida might be what brings you to town, perhaps you'll have a chance to explore more of Gainesville while you are here.

Shands at the University of Florida

North Florida Regional Medical Center

Though North Florida Regional Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Gainesville while you are here.

North Florida Regional Medical Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.