Pleasant Street Vacation Packages 2026 from $326

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 River Ranch Resort & Rodeo

Save 100% on your flight

$326

per person

Oct 2 - Oct 4

found 14 hours ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

8.4/10 Very Good! (540 reviews)

Amazing staff and really beautiful place

Reviewed on Aug 23, 2026

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$537

per person

Sep 25 - Oct 1

found 20 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

9/10 Wonderful! (1,304 reviews)

Westgate Leisure Resort

International Drive District

Save 100% on your flight

$483

per person

Nov 4 - Nov 11

found 21 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.4/10 Very Good! (1,000 reviews)

Naaaaaaaa

Reviewed on Aug 7, 2026

The Delaney Hotel

South Orange

Save 100% on your flight

$1,139

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

9.6/10 Exceptional! (1,187 reviews)

It’s was wonderful

Reviewed on Aug 23, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$936

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

9.2/10 Wonderful! (1,005 reviews)

Everything was nice clean

Reviewed on Aug 22, 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

A cityscape at sunset with buildings, a street, and a palm tree.

Downtown Gainesville

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

University Heights

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

Century Tower at the University of Florida

College Park

While College Park isn't home to many top sights, Ben Hill Griffin Stadium and Stephen C. O'Connell Center are some notable places to visit nearby.

An aerial view of a historic town with red-roofed buildings, a large stadium, and surrounding greenery.

Innovation District

While there might not be top attractions in Innovation District, you can explore the larger area and discover places like Ben Hill Griffin Stadium and Stephen C. O'Connell Center.

A lakeside building surrounded by trees and a calm body of water.

Duckpond

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

Pleasant Street Hotel Deals

Hotel Eleo at the University of Florida

1514 Southwest 14th Street Gainesville FL

Fully refundableReserve now, pay when you stay

$149 nightly

$167 total

Aug 29 - Aug 30

Total with taxes and fees

9.4/10 Exceptional! (1,283 reviews)

"Excellent"

Reviewed on Aug 23, 2026

Drury Inn & Suites Gainesville

4000 Southwest 40th Blvd Gainesville FL

Fully refundableReserve now, pay when you stay

$103 nightly

$116 total

Sep 2 - Sep 3

Total with taxes and fees

Hotel Indigo Gainesville-Celebration Pointe by IHG

5020 SW 30th Lane Gainesville FL

Fully refundable

$98 nightly

$110 total

Aug 31 - Sep 1

Total with taxes and fees

See all 827 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.