Title: Pleasant Street Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $557 Expedia.ca

[Pleasant Street Travel Guide](https://expedia.ca/Gainesville-Pleasant-Street.dx553248635976471970)[Hotels in Pleasant Street](https://expedia.ca/Pleasant-Street-Gainesville-Hotels.0-n553248635976471970-0.Travel-Guide-Filter-Hotels)[Flights to Gainesville](https://expedia.ca/Cheap-Flights-To-Gainesville.d6048189.Travel-Guide-Flights)[Things to do in Gainesville](https://expedia.ca/Things-To-Do-In-Gainesville.d6048189.Travel-Guide-Activities)[Pleasant Street Car Rentals](https://expedia.ca/Car-Rentals-In-Pleasant-Street.d553248635976471970.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Pleasant Street Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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Save up to CA $1,096 when you book a flight and hotel together\*
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## Top Holiday Package Deals in Pleasant Street

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

CA $557

per person

May 23 - May 27

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YTO) 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

![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

CA $567

per person

May 23 - May 27

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YTO) 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 Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/62319b88_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Town Center Resort

CA $979

per person

Apr 29 - May 6

found 17 hours ago

Roundtrip flight included

Halifax (YHZ) to Orlando (MCO)

8/10 Very Good! (1,510 reviews)

Elevator situation was tough. Staff used them and you would be stuck waiting for elevators for a long time. Guest reserve all the pool seats and no seating. 1 pool you have to pay to use so really only 1 other pool that’s large. Otherwise really nice place.

Reviewed on Mar 22, 2026

![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Lakes Resort & Spa Universal Studios Area

CA $991

per person

Apr 29 - May 6

found 17 hours ago

Roundtrip flight included

Halifax (YHZ) to Orlando (MCO)

8.4/10 Very Good! (5,960 reviews)

clean room. in and out very easy

Reviewed on Mar 21, 2026

![Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive](https://images.trvl-media.com/lodging/1000000/900000/897700/897604/w3837h2573x3y0-0a2a5f86_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

CA $802

per person

Jun 10 - Jun 15

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Orlando (MCO)

7.8/10 Good! (381 reviews)

Very clean. Smell Good. Good rooms

Reviewed on Mar 20, 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.ca/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.ca/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

 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.ca/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.ca/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.ca/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.ca/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

CA $106

CA $119 total

Apr 6 - Apr 7

includes taxes & fees

8.4/10 Very Good! (1,866 reviews)

It lacked a lot

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%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

CA $121

CA $136 total

Apr 5 - Apr 6

includes taxes & fees

9.2/10 Wonderful! (1,731 reviews)

The facilities were clean and the room was also clean. The room furniture looked a bit worn, but that was not a major issue. The beds were comfortable which is important. Breakfast was good also.

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%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

CA $133

CA $150 total

Mar 29 - Mar 30

includes taxes & fees

7.8/10 Good! (1,005 reviews)

Excellent

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=49617&PinnedHotelID=49617&HadPinnedHotel=true&regionId=553248635976471970)

[See all 838 properties in Pleasant Street](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F03%2F2026&endDate=24%2F03%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.ca/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.ca/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)

Family Vacations

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

## Frequently asked questions

### How much does a Pleasant Street vacation package cost?

### How do I get a cheap travel package to Pleasant Street?

### Where should I stay in Pleasant Street?

### What are the top hotels in Pleasant Street?

### How far in advance should I book my Pleasant Street vacation?

### What does an Expedia Pleasant Street travel package include?

### What should I know before booking a Pleasant Street travel package?

### Can I choose my airline with a Pleasant Street Expedia vacation package?

### If I'm not able to travel, can I cancel my Pleasant Street vacation package?

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

#### Shands at the University of Florida

Though Shands at the University of Florida might be what brings you to town, perhaps you'll have a chance to explore more of Gainesville while you are here. 

[](https://expedia.ca/Shands-At-The-University-Of-Florida-Gainesville.d6187967.Vacation-Attraction)

#### North Florida Regional Medical Center

Though North Florida Regional Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Gainesville while you are here. 

[](https://expedia.ca/North-Florida-Regional-Medical-Center-Gainesville.d6187962.Vacation-Attraction)

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