Santiago Vacations from $479

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Your Santiago Vacation

Whatever your travel style, you can discover it all with a tailor-made Santiago vacation package. Spend your next break uncovering this neighborhood's golfing and its other appeals. Want to do some sightseeing during your trip to Santiago? Pencil in a visit to nearby attractions like The Villages Market Square, Nancy Lopez Legacy Golf & Country Club and Orange Blossom Hills Golf & Country Club. Don't just dream it — make it happen! Reserve your perfect Santiago vacation with Expedia and get to where you're going your way.

The Latest Santiago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel pool area with multiple lounge chairs and a hot tub.
    Jan 10 - Jan 16

    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight

    International Drive District
    6 nights
    3.0 star property
    7.8/10 - Good (641 reviews)
    "They were very obnoxious about us moving our car as we were checking in and unloading. The main hotel where the pictures were taken was nice but we were put in the back building that was run down and old."
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    PSM - MCO • 1 stop MCO - BOS • Nonstop
    $845
    $479
    per traveler
    found 1 day ago
    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
  • A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a clear sky.
    Jan 25 - Jan 30

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,328
    $609
    per traveler
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • A stone wall, a brown sofa with orange and yellow cushions, a glass table with a fire feature, and a wooden door with decorative glass panels.
    Jan 25 - Jan 30

    The Delaney Hotel + Flight

    South Orange
    5 nights
    3.5 star property
    9.6/10 - Exceptional (1,248 reviews)
    "First off the location! But LOVED EVERYTHING!"
    Reviewed November 9, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,029
    $527
    per traveler
    found 1 day ago
    The Delaney Hotel
  • A spacious lobby with high ceilings, wooden beams, and a large window offering a view of the sky. Furnishings include wicker chairs and tables, and the area is well-lit with hanging lamps.
    Dec 23 - Dec 27

    Disney's Animal Kingdom Lodge + Flight

    Bay Lake
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,005 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $2,935
    $1,675
    per traveler
    found 1 day ago
    Disney's Animal Kingdom Lodge
  • A swimming pool with multiple water features, surrounded by palm trees and hotel buildings.
    Jan 17 - Jan 23

    Magical Moment Vacation Condos + Flight

    International Drive District
    6 nights
    4.5 star property
    6.4/10 - (10 reviews)
    "La propiedad está muy, pero muy bien ubicada, cerca de todo lo principal en Orlando y muchos restaurantes alrededor, el complex es muy bonito, la piscina es grande y el personal es muy amable, el gimnasio es extremadamente sencillo. Los apartamentos vienen equipados con cocina, lavadora, secadora, pero si tú buscas cocinar tus comidas como yo y mi familia, vas a sufrir porque la cocina casi no tienen utensilios, solo un sartén, una olla pequeña, un cuchillo para cortar y por supuesto platos y..."
    Reviewed October 25, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • 1 stop
    $1,211
    $732
    per traveler
    found 1 day ago
    Magical Moment Vacation Condos

Where to stay in Santiago

Find the best Santiago areas and neighborhoods for the activities you enjoy most.
Two blue boats docked at a pier with a lighthouse in the background.
Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Lake Sumter Landing

While visiting Lake Sumter Landing, you might make a stop by sights like The Villages Market Square and Lake Sumter.

A golf course with sand bunkers, trees, and residential areas.

Virginia Trace

While Virginia Trace isn't home to many top sights, The Villages Market Square and Lake Sumter are some notable places to visit nearby.

A grove of trees with Spanish moss.

Sunset Pointe

Though Sunset Pointe might not have many top sights, you can venture to the surrounding area to see attractions like Cane Garden Country Club and The Villages Market Square.

A pathway lined with palm trees and a building with a red roof in the background.

Duval

While Duval isn't home to many top sights, Cane Garden Country Club and The Villages Market Square are some notable places to visit nearby.

Bonita

While Bonita might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Cane Garden Country Club and The Villages Market Square.

Santiago Hotel Deals

A hotel room with a bed, a blue sofa, a desk with a lamp, a large bathtub, and a mirror on the wall.

Comfort Suites Lady Lake - The Villages

Comfort Suites Lady Lake - The Villages
2.5 star property
2.4 mi from Santiago
9.0 out of 10, Wonderful, (1,005 reviews)
"Parking and staff"
$88 nightly
The price is $98
Nov 29 - Nov 30
Total with taxes and fees
Comfort Suites Lady Lake - 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.
See all properties in Santiago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.