Search Deals on
The Villages Market Square Vacation Packages

Build your package with 2 more options

The Villages Market Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Lifetime of Vacations Resort

Lifetime of Vacations Resort

3 out of 5
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3-star condo in Kissimmee. Enjoy a fitness center, a business center, and a garden. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
per person
Jun 6 - Jun 13
found 3 hours 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.
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
per person
Jun 22 - Jun 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star beach hotel in Daytona Beach Shores. Enjoy free WiFi, a full-service spa, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Daytona International Speedway and Beach at Daytona Beach are located nearby.
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free parking, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orlando Vineland Premium Outlets and Disney Springs™ are located nearby.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 13
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.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 16
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.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Daytona International Speedway and Daytona Beach Pier are located nearby.
Embassy Suites by Hilton Orlando Lake Buena Vista Resort

Embassy Suites by Hilton Orlando Lake Buena Vista Resort

4 out of 5
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Orlando Vineland Premium Outlets and Disney Springs™ are located nearby.
Barefoot Suites

Barefoot Suites

3 out of 5
per person
Jun 16 - Jun 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3-star family-friendly aparthotel in Kissimmee. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the helpful staff and the overall value in our reviews. Popular attractions Old Town and ESPN Wide World of Sports are located nearby.
Hilton Daytona Beach Oceanfront Resort

Hilton Daytona Beach Oceanfront Resort

4 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star beach hotel in Daytona Beach. Enjoy 2 outdoor pools, 4 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Daytona International Speedway and Daytona Beach Boardwalk are located nearby.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
May 31 - 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 WiFi, free parking, and 14 outdoor pools. 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.

3-4 Night Vacations in The Villages Market Square

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Florida Center
Save 100% on your flight
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 8
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

5-7 Night Vacations in The Villages Market Square

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
per person
Jun 6 - Jun 13
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
per person
Jun 22 - Jun 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

The Villages Market Square Last Minute Hotel Deals

The Waterfront Inn
The Waterfront Inn
3 out of 5
1105 Lake Shore Drive, The Villages, FL
Stay at this 3-star business-friendly hotel in The Villages. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
The Waterfront Inn
Hampton Inn & Suites Lady Lake/The Villages
Hampton Inn & Suites Lady Lake/The Villages
3 out of 5
11727 Ne 63 Rd Dr, Lady Lake, FL
Stay at this 3-star business-friendly hotel in The Villages. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hampton Inn & Suites Lady Lake/The Villages
Sunny Home w/ Golf Cart in The Villages!
Sunny Home w/ Golf Cart in The Villages!
3 out of 5
The Villages
Stay at this 3-star cottage in The Villages. Enjoy free parking, a business center, and air conditioning. Popular attractions Spanish Springs Town Square and ...
Sunny Home w/ Golf Cart in The Villages!
See all 1,648 properties in The Villages Market Square
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.

Discover Other Travel Deals