Pleasant Street Holidays from £635

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Your Pleasant Street Holiday

Your next great adventure is calling out to you with a holiday package to Pleasant Street. Food, fun and nonstop good times — you're sure to find it in this neighbourhood. Kick off your trip to Pleasant Street by heading to nearby attractions such as University of Florida, Florida Museum of Natural History and Ben Hill Griffin Stadium. No matter what your dream Pleasant Street holiday may look like, you can turn it into reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was £1,009, price is now £635 per person
£635
per person
25 Sept - 29 Sept
found 1 day ago
Return direct flight included
London (LHR) to Orlando (MCO)
8.8/10 Excellent! (1,013 reviews)
This was a good time!

Reviewed on 23 Aug 2025

ette hotel

ette hotel

5 out of 5
Save 100% on your flight
Price was £1,629, price is now £962 per person
£962
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
London (LHR) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on 11 Aug 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Save 100% on your flight
Price was £1,861, price is now £1,139 per person
£1,139
per person
1 Nov - 8 Nov
found 1 day ago
Return flight included
London (LON) to Orlando (MCO)
9/10 Wonderful! (1,000 reviews)
What a wonderful experience!. We loved our little cottage, it was perfect space for us and to have somme friends and family visit. The tickets to the water park was a plus!, not crowded and perfect, definitely work the money!

Reviewed on 19 Aug 2025

Conrad Orlando at Evermore

Conrad Orlando at Evermore

5 out of 5
Save 100% on your flight
Price was £1,792, price is now £1,186 per person
£1,186
per person
26 Sept - 3 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Orlando (MCO)
9.4/10 Exceptional! (252 reviews)
Amazing luxurious property! The Evermore lagoon and private beach area for Conrad guests was incredible! Staff were extremely friendly and helpful! Will definitely visit again!

Reviewed on 21 Aug 2025

Villatel Village at Solterra Resort

Villatel Village at Solterra Resort

4.5 out of 5
Save 100% on your flight
Price was £1,941, price is now £1,298 per person
£1,298
per person
26 Sept - 3 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Orlando (MCO)
No reviews
One of the best vacations I’ve taken in awhile because of this property. With everything in Orlando to do you would think you’d want to spend most of your time outside the villa but NO. It’s so much fun to be had inside that that’s what we preferred even over Disney parks!

Reviewed on 24 Aug 2025

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
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University Heights

University Heights might not have many top sights, but Ben Hill Griffin Stadium and Hippodrome State Theatre are two attractions nearby that you can check out.

Find hotels in University Heights

Top hotels in Pleasant Street

Sleep Inn & Suites University/Shands

Sleep Inn & Suites University/Shands

2.5 out of 5
4110 SW 40th Boulevard, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is £72 per night from 31 Aug to 1 Sept
£72
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Fantastic place to stay! Would definitely stay there again."

Reviewed on 25 Aug 2025

Sleep Inn & Suites University/Shands
DoubleTree by Hilton Gainesville

DoubleTree by Hilton Gainesville

4 out of 5
3726 Sw 40th Blvd, Gainesville, FL
The price is £73 per night from 11 Sept to 12 Sept
£73
11 Sept - 12 Sept
includes taxes & fees
7.6/10 Good! (1,007 reviews)
"Very central to everything"

Reviewed on 25 Aug 2025

DoubleTree by Hilton Gainesville
Hyatt Place Gainesville Downtown

Hyatt Place Gainesville Downtown

3 out of 5
212 SE 1ST STREET,, Gainesville, FL
The price is £87 per night from 2 Sept to 3 Sept
£87
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,058 reviews)
"⭐️⭐️⭐️⭐️⭐️ “Great stay during my daughter’s move-in at UF! The hotel is modern, clean, and very convenient to campus. Spacious rooms and kind staff made us feel right at home.”"

Reviewed on 24 Aug 2025

Hyatt Place Gainesville Downtown
See all 773 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Pleasant Street travel package cost?
Go from wondering to wandering with our Pleasant Street travel packages, which start from only £635. Select the flights and hotels that fit your travel plans. Then, add on a few tours or experiences for an incredible escape.
If I'm not able to travel, can I cancel my Pleasant Street travel package?
Don't worry if you're rethinking your Pleasant Street travel package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that life can occasionally throw a spanner in the travel works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're here to help.
How do I get a cheap travel package to Pleasant Street?
You'll save a pile of money if you bundle your car rentals, hotels and flights into a Pleasant Street travel package. Sometimes cheap means fewer choices. But that's not the case with Expedia. We offer over 550 air carriers and 1,000,000 properties globally, which means you'll always have plenty of options to choose from. Want to save even more? Add some interesting activities to your package deal to unlock even bigger bargains! After all, travel is about more than simply getting to your destination.
Does Expedia offer Book Now, Pay Later Pleasant Street holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a dream getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in convenient monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your trip over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Pleasant Street?
A journey to Pleasant Street isn't complete without stopping by University of Florida and Florida Museum of Natural History. Book a room nearby so you can easily access these popular sights.
What are the top hotels in Pleasant Street?
If this will be your first visit to Pleasant Street, book a room at Country Inn & Suites by Radisson, Gainesville, FL or hom hotel + suites, Trademark Collection by Wyndham. Both will make you feel at home and are favourites among many travellers.
How far in advance should I book my Pleasant Street holiday?
Savvy travellers will likely want to book as early as possible. You can usually look up international fares on Expedia up to 12 months before your flight. If you're purchasing tickets last minute, fear not. Discounted prices sometimes appear just weeks before departure dates.
What does an Expedia Pleasant Street travel package include?
Rental cars, hotels and flights — we have them covered. With Expedia, you can shape your Pleasant Street package the way you like it. All you have to do is decide what you need. Once you've made your booking, you can add extras like tours and activities. The more you bundle, the bigger your savings!
What should I know before booking a Pleasant Street travel package?
Tailor deals that fit your budget with an Expedia package. Hotels, flights, rental cars — we've got them all. You'll save big bucks just for bundling your bookings. Whether you're going on a winter snow adventure or venturing someplace warm, your dream getaway is only clicks away.
Can I choose my airline with a Pleasant Street Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the flexibility to pick from available flights, hotels and activities that fit your needs.

Popular places to visit

Shands at the University of Florida

If Shands at the University of Florida is what brings you to town, hopefully you'll have a chance to explore more of Gainesville.

Shands at the University of Florida

Things to do

Night Gator Eyes A Unique Florida Ecotour

Night Gator Eyes A Unique Florida Ecotour

£29
per adult
Night Gator Eyes A Unique Florida Ecotour
See all activities in Gainesville

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.