Pleasant Street Vacation Packages for 2025

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Pleasant Street Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Worcester (ORH) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Worcester (ORH) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye at ICON Park are located nearby.

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Worcester (ORH) to Orlando (MCO)
Stay at this 4-star spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions The Orlando Eye at ICON Park and Aquatica are located nearby.

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Worcester (ORH) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

4 out of 5
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Worcester (ORH) to Orlando (MCO)
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Worcester (ORH) to Orlando (MCO)
Stay at this 4-star spa condo in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney Springs™ and Old Town are located nearby.

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Top Hotel Deals

Hotel Eleo at the University of Florida

Hotel Eleo at the University of Florida

3 out of 5
1514 Southwest 14th Street, Gainesville, FL
2.34 km from Pleasant Street
Stay at this 3-star business-friendly hotel in Gainesville. Enjoy free WiFi, free valet parking, and breakfast (surcharge). Our guests praise the restaurant ...
Hotel Indigo Gainesville-Celebration Pointe by IHG

Hotel Indigo Gainesville-Celebration Pointe by IHG

3.5 out of 5
5020 SW 30th Lane, Gainesville, FL
7.45 km from Pleasant Street
Stay at this 3.5-star business-friendly hotel in Gainesville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our ...
hom hotel + suites, Trademark Collection by Wyndham

hom hotel + suites, Trademark Collection by Wyndham

2.5 out of 5
3905 Sw 43rd St, Gainesville, FL
7.22 km from Pleasant Street
Book a stay at this business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Gateway Grand

Best Western Gateway Grand

3 out of 5
4200 NW 97th Blvd, Gainesville, FL
12.57 km from Pleasant Street
Stay at this 3-star business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
Country Inn & Suites by Radisson, Gainesville, FL

Country Inn & Suites by Radisson, Gainesville, FL

3 out of 5
4015 Sw 43rd St, Gainesville, FL
7.23 km from Pleasant Street
Stay at this 3-star business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Gainesville Downtown

Hyatt Place Gainesville Downtown

3 out of 5
212 SE 1ST STREET,, Gainesville, FL
0.74 km from Pleasant Street
Stay at this 3-star business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful ...
Red Roof Inn PLUS+ Gainesville

Red Roof Inn PLUS+ Gainesville

2.5 out of 5
3500 Southwest 42nd St, Gainesville, FL
6.85 km from Pleasant Street
Stay at this hotel in Gainesville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Drury Inn & Suites Gainesville

Drury Inn & Suites Gainesville

3 out of 5
4000 Southwest 40th Blvd, Gainesville, FL
6.88 km from Pleasant Street
Stay at this 3-star business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
DoubleTree by Hilton Gainesville

DoubleTree by Hilton Gainesville

4 out of 5
3726 Sw 40th Blvd, Gainesville, FL
6.74 km from Pleasant Street
Stay at this 4-star hotel in Gainesville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in ...
Comfort Suites Gainesville near University

Comfort Suites Gainesville near University

2.5 out of 5
2603 SW 13TH STREET, Gainesville, FL
3.23 km from Pleasant Street
Book a stay at this business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sleep Inn & Suites University/Shands

Sleep Inn & Suites University/Shands

2.5 out of 5
4110 SW 40th Boulevard, Gainesville, FL
6.86 km from Pleasant Street
Book a stay at this business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Super 8 by Wyndham Gainesville I-75 Hospital University Area

Super 8 by Wyndham Gainesville I-75 Hospital University Area

2 out of 5
4202 SW 40th Blvd, Gainesville, FL
6.92 km from Pleasant Street
Book a stay at this business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn Gainesville near University

Quality Inn Gainesville near University

2.5 out of 5
2435 Sw 13th Street, Gainesville, FL
3.08 km from Pleasant Street
Book a stay at this business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
La Quinta by Wyndham Gainesville

La Quinta by Wyndham Gainesville

3 out of 5
908 NW 69 Terrace, Gainesville, FL
8.6 km from Pleasant Street
Stay at this 3-star business-friendly motel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Inn University

Comfort Inn University

2.5 out of 5
3440 SW 40th Blvd, Gainesville, FL
6.87 km from Pleasant Street
Book a stay at this business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Sat, Jun 21 - Sat, Jun 28
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Jun 21 from Portsmouth Intl. to Orlando Intl., returning Sat, Jun 28, priced at $117 found 1 day ago
Spirit Airlines
Sat, Oct 4 - Wed, Oct 15
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$120 Roundtrip, found 11 hours ago
$120
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Sat, Oct 4 from Detroit Metropolitan Wayne County to Orlando Intl., returning Wed, Oct 15, priced at $120 found 11 hours ago
Spirit Airlines
Sat, Oct 18 - Tue, Oct 21
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$120 Roundtrip, found 3 hours ago
$120
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, Oct 18 from Newark Liberty Intl. Airport to Orlando Intl., returning Tue, Oct 21, priced at $120 found 3 hours ago
Spirit Airlines
Tue, Jul 15 - Sat, Jul 19
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$120 Roundtrip, found 13 hours ago
$120
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Tue, Jul 15 from Philadelphia Intl. to Orlando Intl., returning Sat, Jul 19, priced at $120 found 13 hours ago