Title: Pleasant Street Vacation Packages 2026 from $309 | Expedia.com

[Hotels in Pleasant Street](https://expedia.com/Pleasant-Street-Gainesville-Hotels.0-n553248635976471970-0.Travel-Guide-Filter-Hotels)[Flights to Gainesville](https://expedia.com/Cheap-Flights-To-Gainesville.d6048189.Travel-Guide-Flights)[Things to do in Gainesville](https://expedia.com/Things-To-Do-In-Gainesville.d6048189.Travel-Guide-Activities)[Car Rentals in Pleasant Street](https://expedia.com/Car-Rentals-In-Pleasant-Street.d553248635976471970.Car-Rental-Guide)

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# Pleasant Street Vacations from $309

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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](https://www.expedia.com/University-Of-Florida-Gainesville.d6068631.Vacation-Attraction), [Florida Museum of Natural History](https://www.expedia.com/Florida-Museum-Of-Natural-History-Gainesville.d6068619.Vacation-Attraction) and [Ben Hill Griffin Stadium](https://www.expedia.com/Ben-Hill-Griffin-Stadium-Gainesville.d6068633.Vacation-Attraction) 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 Vacation Villas Resort](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Vacation Villas Resort

Save 100% on your flight

$309

per person

May 3 - May 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

8/10 Very Good! (1,820 reviews)

Housekeeping apparently costs $180 USD unless you're there for over 14 days to then qualify for house keeping on day 15 free of charge. Our pool towels were missing from our room and the playpen we requested for our baby was broken. The pools were filled with debris (understandable seeing as there is a lot of foliage around the pools) but no maintence people clean it out throughout the day. The arcade is EXPENSIVE. The games are 20+ tickets each. The coffee stand closes in the (very) early afternoon. Front desk staff doesn't communicate well. This place nickel and dimes you for everything. The elevator had a communication failure and was beeping the entire stay. If you're looking for a family fun property like this, stay at The Grove down the road. It's better, cheaper, more updated rooms and the waterpark is included in your stay unlike this resort.

Reviewed on Mar 20, 2026

![Palazzo Lakeside Hotel](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/f253be82_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Palazzo Lakeside Hotel

$525

per person

Apr 20 - Apr 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.2/10 Very Good! (5,182 reviews)

I had an almost perfect stay at this hotel. The rooms were spotless, the beds felt like sleeping on a well-trained cloud, and the staff managed that rare balance of being both genuinely friendly and impressively competent (no small feat). The front desk sailor uniforms were not needed as they stood out with their exceptional service alone. That said, there’s one tiny thing keeping it from total legend status: the bar situation. Or rather, the lack of a proper one. There’s nowhere to casually sip something delightful while hanging out with your friends. A cozy, lively bar would elevate this place from “fantastic” to “I will never shut up about it.” Still, if your idea of a great stay involves comfort, style, and people who clearly know what they’re doing, this hotel absolutely delivers. Just plan your celebratory nightcap elsewhere.

Reviewed on Mar 20, 2026

![Westgate Towers Resort](https://images.trvl-media.com/lodging/1000000/180000/170900/170878/0a149867_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Towers Resort

Save 100% on your flight

$325

per person

May 3 - May 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

8.6/10 Excellent! (1,004 reviews)

It was very nice, enjoyed our stay. Nice and clean.

Reviewed on Mar 19, 2026

![Westgate Blue Tree Resort in Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/200000/191000/190971/b8eca031_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

$401

per person

May 3 - May 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

8.6/10 Excellent! (1,005 reviews)

We didn’t use the pool , we came down for a work vacation so was busy during the day but I walked each day and observed the pool was very busy especially the hot tub

Reviewed on Mar 12, 2026

![Westgate Cocoa Beach Resort](https://images.trvl-media.com/lodging/1000000/860000/852400/852306/e2b1c912_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Cocoa Beach Resort

Save 100% on your flight

$1,101

per person

Apr 19 - Apr 24

just found

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

8.6/10 Excellent! (525 reviews)

Clean rooms, nice staff, good amenities!

Reviewed on Jan 25, 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](https://expedia.com/Gainesville-Pleasant-Street.dx553248635976471970)

![Gainesville, Florida, USA Skyline](https://images.trvl-media.com/place/939293992653533184/e7dd1f4a-fd98-436e-b9bc-d5bca93f6e46.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 Hippodrome State Theatre. 

[Find hotel + flight trips in Downtown Gainesville](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Gainesville&DestID=939293992653533184&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Closeup of alligator back lying inside marsh swamp in Paynes Prairie Preserve State Park in Gainesville, Florida in sunlight](https://images.trvl-media.com/place/553248635976471424/055eee54-c788-4a46-94f4-cefb0e4d75cc.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 hotel + flight trips in University Heights](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=University%20Heights&DestID=553248635976471424&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in College Park](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=College%20Park&DestID=944716499560566784&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Southern live oak tree branches with sunburst through hanging Spanish moss in Paynes Prairie Preserve State Park in Florida and sunlight in background](https://images.trvl-media.com/place/553248635976474384/4e47067e-034f-48c6-a2b0-e84d895dfdda.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Haile Plantation

 If you're spending some time in Haile Plantation, Haile Plantation Golf and Country Club and Haile Village Center are top sights worth seeing. 

[Find hotel + flight trips in Haile Plantation](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Haile%20Plantation&DestID=553248635976474384&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Photo of Lake Alice and a portion of the Baughman Center on the campus of the University of Florida in Gainesville](https://images.trvl-media.com/place/553248635976470698/28d00b3c-09f4-4b7d-9c99-c8508c6caaac.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in Duckpond](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Duckpond&DestID=553248635976470698&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Pleasant Street Hotel Deals

![HOM Hotel Gainesville, SureStay Collection by Best Western](https://images.trvl-media.com/lodging/1000000/210000/200800/200755/8a6fa57c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

HOM Hotel Gainesville, SureStay Collection by Best Western

3905 Sw 43Rd St Gainesville FL

Fully refundableReserve now, pay when you stay

$77 nightly

$87 total

Apr 6 - Apr 7

Total with taxes and fees

8.4/10 Very Good! (1,862 reviews)

Exceeded my expectations.

Reviewed on Mar 20, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=200755&PinnedHotelID=200755&HadPinnedHotel=true&regionId=553248635976471970)

![Country Inn & Suites by Radisson, Gainesville, FL](https://images.trvl-media.com/lodging/2000000/1290000/1289100/1289043/e387508a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Country Inn & Suites by Radisson, Gainesville, FL

4015 Sw 43rd St Gainesville FL

Fully refundable

$88 nightly

$99 total

Apr 5 - Apr 6

Total with taxes and fees

9.2/10 Wonderful! (1,726 reviews)

Everyone there was super friendly from my check-in where the front desk (Frank I believe) and the manager helped me find info on local activities to the housekeeping staff that were all friendly when passing to the wonderful lady that kept everything clean and well stocked at breakfast. Convenient ...

Reviewed on Mar 20, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=1289043&PinnedHotelID=1289043&HadPinnedHotel=true&regionId=553248635976471970)

![DoubleTree by Hilton Gainesville](https://images.trvl-media.com/lodging/1000000/50000/49700/49617/13133f5c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

DoubleTree by Hilton Gainesville

3726 Sw 40th Blvd Gainesville FL

Fully refundableReserve now, pay when you stay

$97 nightly

$109 total

Mar 29 - Mar 30

Total with taxes and fees

7.8/10 Good! (1,002 reviews)

Most of the said amenities during booking not working. Checked in and when changed for fitness time; I was told it’s not working- this was parts of my main interests when I chose the hotel. Smoke detector in my room out of battery and noisy beeping all the night- reported to the front desk 3 different ...

Reviewed on Mar 19, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=49617&PinnedHotelID=49617&HadPinnedHotel=true&regionId=553248635976471970)

[See all 836 properties in Pleasant Street](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F21%2F2026&endDate=3%2F22%2F2026&regionId=553248635976471970)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Kid Friendly Vacations

[](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ Friendly Vacations

[](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adventure Vacations

[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click)

![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Honeymoon Vacations

[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Mountain Vacations

[](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Fishing Vacations

[](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adults Only Vacations

[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Waterpark Vacations

[](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Scuba Diving Vacations

[](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Yoga Vacations

[](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Cheap Vacations

[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Solo Vacations

[](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click)

### Discover the most popular places to visit in Pleasant Street

![A distant view of The University of Florida in the morning](https://images.trvl-media.com/place/6068631/dc0e407f-c712-4acf-b1ad-0c9896d42d64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.com/University-Of-Florida-Gainesville.d6068631.Vacation-Attraction)

![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. ](https://images.trvl-media.com/place/6048189/0860a82e-f9ae-44b6-ab17-236e4c4e269a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.com/Ben-Hill-Griffin-Stadium-Gainesville.d6068633.Vacation-Attraction)

![Peleides blue morpho butterfly](https://images.trvl-media.com/place/6068619/b5c37750-0581-4f11-9e92-7e3d3daaf0eb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.com/Florida-Museum-Of-Natural-History-Gainesville.d6068619.Vacation-Attraction)

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