Pleasant Street 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 Pleasant Street

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Westgate Cocoa Beach Resort
Westgate Lakes Resort & Spa Universal Studios Area
Boardwalk Inn and Suites

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

Pleasant Street Hotel Deals

Sleep Inn & Suites University/Shands

Sleep Inn & Suites University/Shands

2.5 out of 5
4110 SW 40th Boulevard Gainesville FL
Fully refundable
The price is CA $101 per night from Jun 30 to Jul 1
CA $101
CA $122 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,224 reviews)
"A nice place to stay. Located near restaurants and shopping stores. A nice stay."

Reviewed on Jun 21, 2026

Sleep Inn & Suites University/Shands
HOM Hotel Gainesville, SureStay Collection by Best Western

HOM Hotel Gainesville, SureStay Collection by Best Western

2.5 out of 5
3905 Sw 43Rd St Gainesville FL
Fully refundableReserve now, pay when you stay
The price is CA $91 per night from Jun 24 to Jun 25
CA $91
CA $102 total
Jun 24 - Jun 25
includes taxes & fees
8.6/10 Excellent! (1,992 reviews)
"Pet friendly"

Reviewed on Jun 21, 2026

HOM Hotel Gainesville, SureStay Collection by Best Western
Drury Inn & Suites Gainesville

Drury Inn & Suites Gainesville

3 out of 5
4000 Southwest 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Jun 30 to Jul 1
CA $149
CA $167 total
Jun 30 - Jul 1
includes taxes & fees
9.6/10 Exceptional! (1,480 reviews)
"Very polite and helpful staff. Good breakfast with decent variety. Evening "kickback" was satisfying and included hot food and adult beverage choices."

Reviewed on Jun 21, 2026

Drury Inn & Suites Gainesville
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.

Frequently asked questions

How much does a Pleasant Street vacation package cost?
The cheapest Pleasant Street package is CA $743, 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.

Things to do

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