The Villages Vacation Packages 2026 from $395

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Your The Villages Vacation

Experience the best that The Villages has to offer with a The Villages vacation package. From its golfing to everything else that makes it so fascinating, this neighborhood will delight you from beginning to end. Plan enough time on your itinerary to see renowned nearby sights like Montgomery Hill during your trip to The Villages. Don't just wish for it — make it happen! Secure your perfect The Villages vacation with Expedia and get to where you're going your way.

The Latest The Villages Vacation Packages

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

Marbella Lane Triplex San Jose

Northside

Save 100% on your flight

$395

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to San Jose (SJC)

7.2/10 Good! (45 reviews)

Just only 4 pm can check in. 😞

Reviewed on Apr 28, 2026

Marbella Lane - 3BR Designer Near Valley Fair

Save 100% on your flight

$2,239

per person

Nov 24 - Nov 30

found 13 hours ago

Roundtrip flight included

Seattle (SEA) to San Jose (SJC)

No reviews

@ Marbella Lane - Immaculate & Cozy 3BR Home

Save 100% on your flight

$1,053

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to San Jose (SJC)

No reviews

Aqua Breeze Inn

Westside Santa Cruz

Save 100% on your flight

$471

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to San Jose (SJC)

8.2/10 Very Good! (1,005 reviews)

Exactly what I was hoping for a beautiful room very large with a great view of the pier. Thank you very much

Reviewed on Sep 20, 2026

@ Marbella Lane - 4BR Siliconvalley Gempool House

Berryessa

Save 100% on your flight

$3,747

per person

Nov 24 - Nov 30

found 10 hours ago

Roundtrip flight included

Seattle (SEA) to San Jose (SJC)

No reviews

Where to stay in The Villages

Find the best The Villages areas and neighborhoods for the activities you enjoy most. Learn more about The Villages

A historic building with a clock tower, adjacent to a modern high-rise building.

Downtown San Jose

5 out of top 10 points of interest in this area

This city on San Francisco Bay is not only a technology center, but also filled with cultural and historic attractions.

A cityscape at sunset with a mountain range in the foreground and a river in the distance.

South San Jose

1 out of top 10 points of interest in this area

Southern region of San Jose, California, featuring a mix of businesses, green spaces, and parks. Explore trails like Coyote Creek and Guadalupe River, or visit parks such as Almaden Quicksilver County Park. Easily accessible via VTA stations and highways.

A cityscape with a sunset over mountains.

Willow Glen

Explore this historic downtown with diverse architectural styles, and upscale living. Enjoy shopping and dining in Downtown Willow Glen, and access nearby VTA light rail and Caltrain stations.

A large, ornate building with a red roof and multiple towers, surrounded by well-manicured gardens and palm trees.

West San Jose

1 out of top 10 points of interest in this area

While visiting West San Jose, you might make a stop by sights like Winchester Mystery House and Santana Row Shopping Center.

A highway sign for Exit 2B to San Jose on I-101 South, 1 mile ahead.

North San Jose

If you're spending time in North San Jose, check out sights like Samsung Semiconductor Inc or Topgolf San Jose and hop on the metro to see more the city at Cisco Station or Baypointe Station.

The Villages Hotel Deals

Hyatt Place San Jose Airport

82 Karina Court, Airport San Jose CA

Fully refundableReserve now, pay when you stay

$135 nightly

$159 total

Oct 16 - Oct 17

Total with taxes and fees

9/10 Wonderful! (1,725 reviews)

"The staff were friendly"

Reviewed on Sep 21, 2026

Sonesta Silicon Valley

1820 Barber Ln Milpitas CA

Fully refundableReserve now, pay when you stay

$104 nightly

$119 total

Oct 2 - Oct 3

Total with taxes and fees

9.2/10 Wonderful! (2,240 reviews)

"Nice place"

Reviewed on Sep 21, 2026

Wild Palms, a JdV by Hyatt Hotel

910 E Fremont Ave Sunnyvale CA

Fully refundableReserve now, pay when you stay

$110 nightly

$124 total

Sep 25 - Sep 26

Total with taxes and fees

See all 1,456 properties in The Villages

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.