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Four Seasons Vacations from $516

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The Latest Four Seasons Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Sep 25 - Sep 28

    The Sofia Hotel + Flight

    Downtown San Diego
    3 nights
    3.5 star property
    8.6/10 - Excellent (2,389 reviews)
    Roundtrip • Chicago (CHI) - San Diego (SAN)
    ORD - SAN • 1 stop SAN - RFD • 1 stop
    Save 100% on your flight
    $973
    $516
    per traveler
    found 1 day ago
    The Sofia Hotel
  • Desk, laptop workspace, iron/ironing board (on request), WiFi (free)
    Sep 26 - Oct 1

    Hyland Inn Near Legoland + Flight

    Olde Carlsbad
    5 nights
    3.0 star property
    7.8/10 - Good (1,007 reviews)
    Roundtrip • New York (JFK) - San Diego (SAN)
    JFK - SAN • Nonstop SAN - JFK • 1 stop
    Save 100% on your flight
    $1,163
    $547
    per traveler
    found 1 day ago
    Hyland Inn Near Legoland
  • King Suite with Ocean View | Terrace/patio
    Sep 18 - Sep 23

    Los Bungalows + Flight

    Imperial Beach
    5 nights
    2.5 star property
    8.2/10 - Very Good (544 reviews)
    "Awsome place to stay close to the beach"
    Reviewed July 16, 2026
    Roundtrip • Denver (DEN) - San Diego (SAN)
    DEN - SAN • Nonstop SAN - DEN • Nonstop
    Save 100% on your flight
    $1,004
    $593
    per traveler
    found 1 day ago
    Los Bungalows
  • Sand | Terrace/patio
    Sep 26 - Oct 1

    Ocean Villas of Carlsbad + Flight

    Carlsbad Village
    5 nights
    3.0 star property
    9.0/10 - Wonderful (20 reviews)
    "Great location and incredible views. Large deck and living room. Ellie in the office is great"
    Reviewed June 17, 2026
    Roundtrip • New York (JFK) - San Diego (SAN)
    JFK - SAN • Nonstop SAN - JFK • 1 stop
    Save 100% on your flight
    $2,303
    $1,380
    per traveler
    found 1 day ago
    Ocean Villas of Carlsbad
  • Sauna, hot tub, steam room, body treatments, hydrotherapy, facials
    Sep 24 - Sep 28

    Guesthouse Hotel at La Valle + Flight

    Rancho Santa Fe
    4 nights
    4.5 star property
    9.2/10 - Wonderful (167 reviews)
    "We had a great stay! Pool was perfect for young kids!"
    Reviewed July 14, 2026
    Roundtrip • Dallas (DFW) - San Diego (SAN)
    DFW - SAN • Nonstop SAN - DFW • Nonstop
    Save 100% on your flight
    $924
    $579
    per traveler
    found 1 day ago
    Guesthouse Hotel at La Valle