Search Deals on
Windermere Vacation Packages

Build your package with 2 more options

Windermere Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites Orlando East - UCF Area

Quality Inn & Suites Orlando East - UCF Area

2.5 out of 5
Save 100% on your flight
per person
May 6 - May 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Congo River Golf - East Orlando and Waterford Lakes Town Center are located nearby.
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

3.5 out of 5
Save 100% on your flight
per person
May 8 - May 15
found 1 day ago
Roundtrip non-stop flight included
Appleton (ATW) to Orlando (MCO)
Stay at this 3.5-star beach hotel in St. Augustine. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vilano Beach and Castillo de San Marcos National Monument are located nearby.
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
per person
May 28 - Jun 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star spa hotel in Celebration. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the pool and the restaurant in our reviews. Popular attractions ESPN Wide World of Sports Complex and Old Town are located nearby.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
per person
May 21 - May 28
found 1 day ago
Roundtrip non-stop flight included
Appleton (ATW) 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 Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
per person
May 28 - Jun 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.
Alhambra Villas

Alhambra Villas

3 out of 5
Save 100% on your flight
per person
May 6 - May 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3-star family-friendly hotel in Kissimmee. Enjoy free WiFi, a business center, and laundry facilities. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Johnson Island and London Island are located nearby.
Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star family-friendly resort in River Ranch. Enjoy free parking, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
per person
Apr 30 - May 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.

Windermere Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Save 100% on your flight
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
Save 100% on your flight
per person
May 21 - May 25
found 17 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Orlando (MCO)
Encore Resort and Water Park At Reunion by Rentyl

Encore Resort and Water Park At Reunion by Rentyl

5 out of 5
Save 100% on your flight
per person
Jun 2 - Jun 5
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Windermere Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
per person
May 28 - Jun 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Jun 4 - Jun 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

3.5 out of 5
Vilano Beach
Save 100% on your flight
per person
May 8 - May 15
found 1 day ago
Roundtrip non-stop flight included
Appleton (ATW) to Orlando (MCO)
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
per person
May 28 - Jun 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Wed, Apr 9 - Tue, Apr 15
BOS
Logan Intl.
MCO
Orlando Intl.
$54 Roundtrip, found 2 days ago
$54
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Apr 9 from Logan Intl. to Orlando Intl., returning Tue, Apr 15, priced at $54 found 2 days ago
Spirit Airlines
Mon, May 19 - Tue, May 20
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 14 hours ago
$82
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Mon, May 19 from Philadelphia Intl. to Orlando Intl., returning Tue, May 20, priced at $82 found 14 hours ago
Frontier Airlines
Sat, Jun 14 - Tue, Jun 17
TTN
Mercer
MCO
Orlando Intl.
$89 Roundtrip, found 4 days ago
$89
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jun 14 from Mercer to Orlando Intl., returning Tue, Jun 17, priced at $89 found 4 days ago
Spirit Airlines
Sun, Apr 6 - Sun, Apr 13
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Apr 6 from Newark Liberty Intl. Airport to Orlando Intl., returning Sun, Apr 13, priced at $98 found 2 days ago