Pleasant Street Vacations from ￥186,969

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The Latest Pleasant Street Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
Price was ￥275,499, price is now ￥186,969 per person
￥186,969
per person
Feb 14 - Feb 21
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.4/10 Exceptional! (1,777 reviews)
Yes very professional

Reviewed on Dec 22, 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 ￥417,562, price is now ￥243,918 per person
￥243,918
per person
Feb 14 - Feb 21
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
Garbage bags were cheap. Thats my o ly complaint. It was perfect and will stay again

Reviewed on Dec 18, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
Price was ￥328,234, price is now ￥209,326 per person
￥209,326
per person
Feb 14 - Feb 21
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.6/10 Exceptional! (1,002 reviews)
Exceeded my expectations

Reviewed on Dec 21, 2025

Summerville Vacation Homes by Columbia Management

Summerville Vacation Homes by Columbia Management

4 out of 5
Save 100% on your flight
Price was ￥321,744, price is now ￥207,365 per person
￥207,365
per person
Feb 14 - Feb 21
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
8.4/10 Very Good! (152 reviews)
Exactly what we needed for our stay in Disney. Was first time we have stayed off property and besides not getting in to the park early, this place was great. It rained on us every day at the park and was nice to be able to through our jacket in the dryer! On negative i will say is the washer and dryer was loud HA! But other than that place had everythign we needed. Oh and fyi this place was not 3 bed rooms. It was 4! Maybe because it didtn have a bathroom? Not sure but was 4 bedroom 3 and half bath. HA kids liked havign there own rooms with own bathrooms. And so did I! Was thankful we was not crammed on an on park hotel with one room and one bathroom! Had 2 masters with Kings, one upstairs one down, and then the other 2 rooms was up stairs with one being two twins with bathroom then the other room was just a bunk. Would stay here again for sure.

Reviewed on Oct 9, 2025

Villas at Fortune Place

Villas at Fortune Place

3 out of 5
Price was ￥312,481, price is now ￥214,102 per person
￥214,102
per person
Feb 14 - Feb 21
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
8.8/10 Excellent! (137 reviews)
Nice place plenty of room, convenient for the event we attended Thanks

Reviewed on Aug 25, 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

4/5(31 area reviews)

While University Heights isn't home to many top sights, Hippodrome State Theatre and Ben Hill Griffin Stadium are some notable places to visit nearby.

Find hotels in University Heights

Pleasant Street Hotel Deals

DoubleTree by Hilton Gainesville

DoubleTree by Hilton Gainesville

4 out of 5
3726 Sw 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
The price is ￥12,737 per night from Dec 29 to Dec 30
￥12,737
￥14,329 total
Dec 29 - Dec 30
includes taxes & fees
7.6/10 Good! (1,004 reviews)
Excellent Staff Especially The Bartender..She Was Very Friendly And She Fixed My Drink..Tom Collins

Reviewed on Dec 19, 2025

DoubleTree by Hilton Gainesville
Hilton University of Florida Conference Center Gainesville

Hilton University of Florida Conference Center Gainesville

3.5 out of 5
1714 SW 34th St Gainesville FL
Fully refundableReserve now, pay when you stay
The price is ￥15,196 per night from Dec 30 to Dec 31
￥15,196
￥17,096 total
Dec 30 - Dec 31
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
Clean room, very nice hotel.

Reviewed on Dec 21, 2025

Hilton University of Florida Conference Center 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
The price is ￥19,958 per night from Dec 24 to Dec 25
￥19,958
￥22,453 total
Dec 24 - Dec 25
includes taxes & fees
9.2/10 Wonderful! (1,285 reviews)
Spotless room, really cool layout w/great use of space. White noise machine in the room is a very smart and welcome amenity.

Reviewed on Dec 18, 2025

Hotel Eleo at the University of Florida
See all 831 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.

Frequently asked questions

How much does a Pleasant Street vacation package cost?
The cheapest Pleasant Street package is ￥186,969, so your dream escape can become a reality — without spending an arm and a leg. Bundle flights, hotels, car rentals and more to tailor a package that suits you.
How do I get a cheap travel package to Pleasant Street?
Find flights that suit your busy schedule, add a hotel room to your booking and watch the savings pile up with a Pleasant Street vacation package. It's that simple! From flights and hotels to rental cars and tours, Expedia makes traveling cheap and easy. And with over 550 partner airlines and 1,000,000 hotels across the globe to choose from, you won't be short of choice.
Where should I stay in Pleasant Street?
Make sightseeing easy by staying in a hotel just a stone's throw away from Pleasant Street's main attractions. University of Florida and Florida Museum of Natural History are two traveler favorites.
What are the top hotels in Pleasant Street?
If it's comfort and convenience you want, you can't beat Beautiful 7th Floor Condo In Gainesville. Spend your evenings relaxing here and your days checking out Pleasant Street's popular attractions.
How far in advance should I book my Pleasant Street vacation?
It's tricky picking the perfect time for airfares, but we generally say the earlier, the better. Many international journeys on Expedia become available up to a year in advance. If you can't book ahead, don't stress. Bargain prices occasionally appear within a few weeks of departure dates.
What does an Expedia Pleasant Street travel package include?
Travel packages include hotels, rental cars and flights, but you can mix and match them to create your dream Pleasant Street escape. You can also add on activities and experiences once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll get access to discounts you won't find anywhere else.
What should I know before booking a Pleasant Street travel package?
Get ready to save with an Expedia travel package. Combine your flights, rental cars and hotels and land fantastic discounts. Hotels aren't your only choice, though. Book with us and select from beachfront villas, chalets in the middle of mountains and everything in between!
Can I choose my airline with a Pleasant Street Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You're in charge! We have access to more than 550 partner airlines globally, so you have loads of choice when putting together your Pleasant Street adventure.
If I'm not able to travel, can I cancel my Pleasant Street vacation package?
Because we know life is full of surprises, the answer is yes. To learn more, check out our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in Pleasant Street

University of Florida

University of Florida

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
The Florida Museum of Natural History has an amazing osteological and fossil collection

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.

Florida Museum of Natural History

Gainesville Raceway

Catch an event at Gainesville Raceway during your trip to Gainesville. Amble around the area's lakeside or attend a sporting event.

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