Pleasant Street Vacation Packages

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

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Top Holiday Package Deals in Pleasant Street

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 $1,336, price is now CA $680 per person
CA $680
per person
May 22 - May 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8/10 Very Good! (1,886 reviews)
Everything was great! Easy check in, friendly and helpful staff, great amenities, check out was a breeze. It’s also helpful that a Walmart is close for all of those items we forgot to pack.

Reviewed on Apr 20, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,862, price is now CA $892 per person
CA $892
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.4/10 Very Good! (6,254 reviews)
Awesome stay. I had a patio balcony and hottub in my room. So many pools and things to do around the resort.

Reviewed on Apr 21, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was CA $1,787, price is now CA $927 per person
CA $927
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
7.8/10 Good! (441 reviews)
Très décevant pratiquement aucun service de nettoyage de chambre.. la chambre étais à l’extérieur pour y parvenir nous devions prendre l’ascenseur extérieur qui prenais un éternité avant d’arrivée.. et le déjeuner ont dirai que les seuls choix étais du pain .. pas très nourrissent Mais sinon la piscine et la vue étais belle.

Reviewed on Apr 20, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,328, price is now CA $717 per person
CA $717
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.2/10 Very Good! (1,633 reviews)
Our room looked beautiful to the eyes. It did have a mildewy and cigarette smell. The rugs looked filthy my socks got dirty immediately when I took off my shoes. The sofa bed where my son slept had an older mattress. His back was uncomfortable. The furniture and decor definitely needs updating. The wardrobe dresser had a dirty sock or dirty laundry smell. The bathroom door was a little off the hinge and made noise. However, the staff was friendly and polite.

Reviewed on Apr 21, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,306, price is now CA $706 per person
CA $706
per person
May 22 - May 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (1,010 reviews)
The room was beautiful and spacious. Not many things to fo on the property like The westgate down the street but it was still enjoyable. The tvs need updated but thats a personal thing. The shower in our bedroom did not get hot but maintenance came and said the knob was installed wrong so there was nothing they could do at the moment. Thay wasnt too bad though. Everything else was perfect.

Reviewed on Apr 20, 2026

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
Gainesville, Florida, USA Skyline

Downtown Gainesville

If you're looking for some top things to see and do in Downtown Gainesville and surrounding area, you can visit Thomas Center and Hippodrome State Theatre.

Find hotels in Downtown Gainesville

Pleasant Street Hotel Deals

DoubleTree by Hilton Gainesville

DoubleTree by Hilton Gainesville

4 out of 5
3726 Sw 40th Blvd Gainesville FL
The price is CA $143 per night from Apr 26 to Apr 27
CA $143
CA $161 total
Apr 26 - Apr 27
includes taxes & fees
7.8/10 Good! (1,005 reviews)
Great

Reviewed on Apr 20, 2026

DoubleTree by Hilton Gainesville
Country Inn & Suites by Radisson, Gainesville, FL

Country Inn & Suites by Radisson, Gainesville, FL

3 out of 5
4015 Sw 43rd St Gainesville FL
The price is CA $132 per night from Apr 26 to Apr 27
CA $132
CA $148 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,769 reviews)
Nice place ,clean ,comfortable.Breakfast needs to be upgraded

Reviewed on Apr 20, 2026

Country Inn & Suites by Radisson, Gainesville, FL
Sleep Inn & Suites University/Shands

Sleep Inn & Suites University/Shands

2.5 out of 5
4110 SW 40th Boulevard Gainesville FL
The price is CA $113 per night from Apr 26 to Apr 27
CA $113
CA $134 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (1,183 reviews)
Felt safe here. Building and facilities antiquated. Mattress should have been replaced years ago.close to my scheduled venue

Reviewed on Apr 19, 2026

Sleep Inn & Suites University/Shands
See all 845 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 $680, 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

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.