Pleasant Street Vacations from $273

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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 Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was $568, price is now $273 per person
$273
per person
Apr 8 - Apr 12
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Always clean and very cozy my favorite place to stay

Reviewed on Feb 2, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $1,036, price is now $437 per person
$437
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
Clean and comfortable. Especially the bed. We didn't get up with sore hips from a hard matress.

Reviewed on Feb 2, 2026

Flamingo Inn Beachfront

Flamingo Inn Beachfront

2 out of 5
Price was $795, price is now $346 per person
$346
per person
Mar 20 - Mar 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (978 reviews)
It was clean and although it looks a little older everything was very well taken care off and everything worked perfectly. I can honestly say it was the best hotel I’ve stayed where the AC worked extremely well. For the first time I had to actually turn off cause I was too cold which is odd to say. The property manager was very nice and helpful.

Reviewed on Jan 26, 2026

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flight
Price was $927, price is now $417 per person
$417
per person
Mar 20 - Mar 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (1,681 reviews)
Staff very courteous and welcoming. Lobby was nice.

Reviewed on Jan 27, 2026

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $1,520, price is now $718 per person
$718
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
Everything was great! Except the remote in living room did not want to work half the time. But we weren't there much due to visiting Disney. But at night we liked to wind down in living room. We never reached out to the front desk only cuz wasnt big enough deal. Perfect spot! Plenty of places to eat and pick up needed items. At night, traffic was busy, but not too bad. Close to Disney Parks. Very cute townhouses.

Reviewed on Jan 31, 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 Hippodrome State Theatre and Thomas Center.

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
$93 nightly
The price is $104 total per night from Feb 9 to Feb 10
$104 total
Feb 9 - Feb 10
Total with taxes and fees
7.6/10 Good! (1,001 reviews)
👍

Reviewed on Jan 23, 2026

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
$179 nightly
The price is $201 total per night from Feb 8 to Feb 9
$201 total
Feb 8 - Feb 9
Total with taxes and fees
9.2/10 Wonderful! (1,293 reviews)
All perfect

Reviewed on Jan 29, 2026

Hotel Eleo at the University of Florida
Hyatt Place Gainesville Downtown

Hyatt Place Gainesville Downtown

3 out of 5
212 SE 1ST STREET, Gainesville FL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Feb 5 to Feb 6
$123 total
Feb 5 - Feb 6
Total with taxes and fees
9/10 Wonderful! (1,118 reviews)
The location is amazing. The downtown area is restored and has great restaurants, cafes and boutiques. Hotel was nice, unfortunately we missed the breakfast, which is supposed to be great… We had to find parking, because of the location. But a garage was not that far away.

Reviewed on Jan 29, 2026

Hyatt Place Gainesville Downtown
See all 834 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
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Beach Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Pleasant Street

A distant view of The University of Florida in the morning

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
Peleides blue morpho butterfly

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.