Pleasant Street Vacations from $311

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Your Pleasant Street Vacation

Take all the hassle out of planning your next escape by booking a Pleasant Street vacation package. Take in the sights and sounds of this captivating neighborhood and experience what it has to offer. Not sure what to do during your trip to Pleasant Street? Nearby attractions like University of Florida, Florida Museum of Natural History and Ben Hill Griffin Stadium are good places to begin. Expedia will help turn your ideal Pleasant Street vacation into reality, whatever your travel plans or budget.

The Latest Pleasant Street Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $837, price is now $311 per person
$311
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,085 reviews)
Yes room was very nice and staff was super polite and helpful

Reviewed on Nov 22, 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $1,229, price is now $431 per person
$431
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (2,232 reviews)
Great location, Justine at front desk was super nice. Having the mall just there is a great plus. We spent a great night, it was super quiet at night. Clean, well organized, etc. this is our new go to hotel for our Orlando getaways!

Reviewed on Nov 27, 2025

Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

4 out of 5
Price was $1,583, price is now $712 per person
$712
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.4/10 Exceptional! (186 reviews)
Clean rooms and convenient location Poor internet connectivity though It showed full bars of wifi, however, we all apps showed poor connection messages when we attempted to use them.

Reviewed on Nov 22, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $966, price is now $436 per person
$436
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
The place is exceptional and met all of our needs and then some

Reviewed on Nov 12, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was $811, price is now $367 per person
$367
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.6/10 Exceptional! (1,002 reviews)
My husband and I have stayed in this small boutique hotel maybe a dozen times. It is always a pleasure. Staff is wonderful. Rooms are clean. And the location is central to downtown Orlando. We love it.

Reviewed on Nov 28, 2025

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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

4/5(31 area reviews)

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

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
$81 nightly
The price is $91 total per night from Dec 7 to Dec 8
$91 total
Dec 7 - Dec 8
Total with taxes and fees
7.6/10 Good! (1,009 reviews)
Every was amazing… 10/10

Reviewed on Nov 23, 2025

DoubleTree by Hilton Gainesville
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
$139 nightly
The price is $157 total per night from Dec 16 to Dec 17
$157 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (1,289 reviews)
The Hotel Eleo is a good find and great location for a stay in Gainesville. The valet staff was excellent and super quick. The hotel lobby area is nice and clean. My only complaint is the mattress was uncomfortable and the towels are well worn and should be replaced.

Reviewed on Nov 23, 2025

Hotel Eleo at the University of Florida
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
$77 nightly
The price is $87 total per night from Dec 7 to Dec 8
$87 total
Dec 7 - Dec 8
Total with taxes and fees
8.4/10 Very Good! (1,805 reviews)
Personnel were excellent room was cleaned everyday. Can't say enough good things. Inly one thing, I saw two roaches in the bathroom.

Reviewed on Nov 20, 2025

HOM Hotel Gainesville, SureStay Collection by Best Western
See all 806 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.
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Discover the most popular places to visit in Pleasant Street

University of Florida

University of Florida

4.5/5(833 reviews)

Explore the campus of University of Florida, during your trip to Gainesville. Stroll along the lakeside or attend a sporting event in the area.

University of Florida
At the Gators home opener with 90,000 of my closest friends. A football game at Florida Field is an incredible experience. Energy not to be missed. This is probably one of the greatest stadiums in college football.

Ben Hill Griffin Stadium

4.5/5(272 reviews)

Catch an event at Ben Hill Griffin Stadium during your trip to Gainesville. Stroll along the lakeside or attend a sporting event in the area.

Ben Hill Griffin Stadium
The Florida Museum of Natural History has an amazing osteological and fossil collection

Florida Museum of Natural History

4.5/5(171 reviews)

You can spend an afternoon exploring the galleries in Florida Museum of Natural History during your trip to Gainesville. You can attend a sporting event while in the area.

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