Pleasant Street Vacations
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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.
Price found within the past 48 hours. Click for updated prices.
- Westgate Vacation Villas Resort
Aug 6 - Aug 11Westgate Vacation Villas Resort + Flight
Kissimmee5 nights8.2/10 - Very Good (1,963 reviews)"Definitely family friendly"Reviewed June 4, 2026Roundtrip • Newburgh (SWF) - Orlando (MCO)SWF - MCO • Nonstop MCO - LGA • Nonstop - Westgate Towers Resort
Aug 6 - Aug 11Westgate Towers Resort + Flight
Kissimmee5 nights8.6/10 - Excellent (1,001 reviews)"Good"Reviewed May 31, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - LGA • Nonstop - Westgate Town Center Resort
Aug 13 - Aug 19Westgate Town Center Resort + Flight
Kissimmee6 nights8.2/10 - Very Good (1,755 reviews)"Everything was perfect definitely book"Reviewed June 4, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Hammock Beach Golf Resort & Spa
Jul 10 - Jul 15Hammock Beach Golf Resort & Spa + Flight
Palm Coast5 nights8.6/10 - Excellent (1,004 reviews)"Pool area is amazing!! Everything is great and beautiful! But just to use all the amenities it is better to stay at the main tower, not at the Lodge. I booked the room at Lodge just because I wanted to have a better view of the ocean (so I booked an ocean view). That was the only reason! To open the patio door and see the beach! My room ended up being facing the dumpster, and a tent that they have on the side of the property, the entrance of the parking lot… and I could barely see a little bit..."Reviewed June 3, 2026Roundtrip • New York (JFK) - Daytona Beach (DAB)JFK - DAB • Nonstop DAB - JFK • Nonstop$2,623$1,426found 13 hours agoper traveler - Boardwalk Inn and Suites
Jul 10 - Jul 15Boardwalk Inn and Suites + Flight
Davis5 nights8.4/10 - Very Good (1,850 reviews)"The overall experience was excellent. I would stay again and recommend it to my friends."Reviewed June 4, 2026Roundtrip • New York (JFK) - Daytona Beach (DAB)JFK - DAB • Nonstop DAB - JFK • Nonstop
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
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 Depot Park.
Pleasant Street Hotel Deals
Sleep Inn & Suites University/Shands
4110 SW 40th Boulevard Gainesville FL
Fully refundable
$77 nightly
The price is $86 total per night from Jun 28 to Jun 29
$86 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (1,200 reviews)
"The staff was great; the front desk to the breakfast attendant and everyone In between. The beds, bedding, and pillows were comfortable. The place was clean but could use some sprucing up. The wallpaper was worn and peeling in some places and the bathroom fixtures were not in the best shape. The ..."
Reviewed on Jun 4, 2026
Hilton University of Florida Conference Center Gainesville
1714 SW 34th St Gainesville FL
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $128 total per night from Jun 14 to Jun 15
$128 total
Jun 14 - Jun 15
Total with taxes and fees
8.4/10 Very Good! (1,007 reviews)
"the room was super dirty, you need to use hilton honors points or you get charged for wifi, my son got a rash from the pillow case, they don't tell you they don't clean your room, the air conditioner unit was difficult to use and kept defaulting to freezing cold. it is a gross old property and it ..."
Reviewed on May 30, 2026
Drury Inn & Suites Gainesville
4000 Southwest 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $116 total per night from Jun 15 to Jun 16
$116 total
Jun 15 - Jun 16
Total with taxes and fees
9.6/10 Exceptional! (1,463 reviews)
"I write a lot of reviews and I always try to be fair. The hotel could have been cleaner in some areas. Glitz with fingerprints and sticky, poorly maintained areas that are frequented by guests does not impress. The chairs and tables in the dining area still had food on them even after my wife and ..."
Reviewed on Jun 3, 2026
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.
Discover the most popular places to visit in Pleasant Street
University of Florida
Take a campus tour or just explore the area around University of Florida, a top college in Gainesville. Stroll along the lakeside or attend a sporting event in the area.
Ben Hill Griffin Stadium
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.
Florida Museum of Natural History
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.
Things to do
Interlachen: Rodman Reservoir Trophy Bass Fishing Trip
$435
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.