A calm lake with lily pads and reeds in the foreground, surrounded by trees and a cloudy sky.

Photo by Gregg Yutko

Oakland Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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  • The Latest Oakland Vacation Packages

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    Where to stay in Oakland

    Find the best Oakland areas and neighborhoods for the activities you enjoy most.

    A city skyline at dusk with illuminated buildings reflecting on a calm body of water.

    View properties in map for Horizon West

    Horizon West

    While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club.

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    A sunset over a body of water with silhouetted land in the distance and tall grasses in the foreground.

    View properties in map for Vista del Lago

    Vista del Lago

    While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

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    A tree-lined sidewalk with parked cars and a clear sky.

    A street lined with large trees and historic brick buildings, including a 'Local' sign.

    Photo by Shannon Maya

    A bakery interior with a display case, shelves with jars, and a counter with a menu board.

    Photo by JoyFilledWander

    A café with a variety of food items and beverages on display, including boxes of snacks and bottles of wine.

    Photo by JoyFilledWander

    A bar with a polished floor, metal chairs, and a brick wall with a TV.

    Photo by Nancy

    View properties in map for Downtown Winter Garden

    Downtown Winter Garden

    While visiting Downtown Winter Garden, you might make a stop by sights like Garden Theatre and Winter Garden Heritage Museum.

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    A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.

    View properties in map for Killarney

    Killarney

    If you're spending some time in Killarney, Oakland Nature Preserve and Johns Lake are top sights worth seeing.

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    Oakland Hotel Deals

    Kompose Boutique Resort at Theme Parks

    A resort pool area with a winding pool design, lounge chairs, and palm trees.
    • Address: 7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL, 34747, US
    • Location: 24.9 km from Oakland
    • Star rating: 3/5
    • Guest rating: 9.4/10 (Exceptional, 6507 reviews)
    • Price: CA $31, CA $98 total, includes taxes & fees, Nov 17 - Nov 18
    • Review: Very much enjoyed our stay, the room,

    Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

    A large hotel with multiple floors, a central courtyard, and a reflective water feature.
    • Address: 2111 FLAGLER AVE, Winter Garden, FL, 34787, US
    • Location: 19.3 km from Oakland
    • Star rating: 3/5
    • Guest rating: 9.6/10 (Exceptional, 2332 reviews)
    • Price: CA $148, CA $166 total, includes taxes & fees, Nov 29 - Nov 30
    • Review: House cleaning the room very inconsistent but other than that prosperity is awesome

    SPOT X Hotel Orlando/Intl Dr by The Red Collection

    A spacious lobby with a pool table, comfortable seating areas, and a reception desk.
    • Address: 12235 Regency Village Drive, Orlando, FL, 32821, US
    • Location: 23.2 km from Oakland
    • Star rating: 3/5
    • Guest rating: 8.6/10 (Excellent, 3788 reviews)
    • Price: CA $76, CA $111 total, includes taxes & fees, Nov 30 - Dec 1

    Rosen Shingle Creek

    A large indoor swimming pool surrounded by lounge chairs and umbrellas, with a hotel building in the background.
    • Address: 9939 Universal Blvd, Orlando, FL, 32819, US
    • Location: 24.2 km from Oakland
    • Star rating: 4.5/5
    • Guest rating: 9.6/10 (Exceptional, 4997 reviews)
    • Price: CA $142, CA $160 total, includes taxes & fees, Nov 24 - Nov 25

    Orlando Palms Hotel

    A spacious lobby with a red sofa, round tables, and a chandelier.
    • Address: 8601 S Orange Blossom Trl, Orlando, FL, 32809, US
    • Location: 25.8 km from Oakland
    • Star rating: 2.5/5
    • Guest rating: 7.8/10 (Good, 3596 reviews)
    • Price: CA $49, CA $72 total, includes taxes & fees, Dec 1 - Dec 2
    • Review: 房子地理位置很好 附近商场超市餐饮都很多很方便 设施比较老旧但是还算干净,这个价格性价比很棒

    Holiday Inn Orlando International Dr-ICON by IHG

    A Holiday Inn hotel with a modern design, featuring a registration area and a well-lit entrance.
    • Address: 8368 Jamaican Court, Orlando, FL, 32819, US
    • Location: 20 km from Oakland
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 3458 reviews)
    • Price: CA $104, CA $139 total, includes taxes & fees, Dec 13 - Dec 14
    • Review: A+

    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.

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    Frequently Asked Questions

    How much does an Oakland vacation package cost?

    Starting from only CA $701, a vacation package is your portal to affordable travel. Customize your Oakland escape by picking from our great range of airfares, hotels and rental cars.

    How do I get a cheap travel package to Oakland?

    You'll save a ton of money if you bundle your flights, hotels and car rentals into an Oakland vacation package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1,000,000 hotels worldwide, which means you'll always have plenty of options to choose from. Like to save even more? Add some interesting activities to your package deal to unlock even bigger bargains! After all, travel is about more than simply getting to your destination.

    Where should I stay in Oakland?

    With loads to explore in Oakland, we recommend you lock in a hotel near its attractions. West Orange Trail, Garden Theatre and Winter Garden Heritage Museum are some popular ones to add to your itinerary.

    What are the top hotels in Oakland?

    Whether you'll be staying for one night or longer in Oakland, you'll get a good night's rest at The Oak View Place. This place is the first choice for many travelers.

    How far in advance should I book my Oakland vacation?

    While prices change from time to time, we generally recommend booking your seats as soon as possible. Most international fares become available on Expedia up to a year in advance. If circumstances have left you booking last minute, you may still get lucky. Discount prices to Oakland sometimes appear only weeks before departure.

    What does an Expedia Oakland travel package include?

    Rental cars, hotels and flights, or any combination of them — the choice is all yours! Whether you're exploring Oakland on a family road trip or traveling with your friends, there's a package to match your budget and style. Once you've made your booking, why not add on one or two tours as well?

    What should I know before booking an Oakland travel package?

    Locking in all the parts of your getaway together is a simple way to save. Combine car rentals, airfares and hotels into a tidy package. But you're not limited to hotels. Expedia features all kinds of properties, including vacation rentals like beachfront villas and spacious residences. The list goes on!

    Can I choose my airline with an Oakland Expedia vacation package?

    Definitely. Expedia has more than 550 airline partners to pick from worldwide. With all that choice at your fingertips, finding the perfect carrier to fly you to Oakland will be a cinch.

    If I'm not able to travel, can I cancel my Oakland vacation package?

    You sure can, and we'll help you every step of the way. You may be able to cancel or amend your Oakland vacation package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life throws you a curveball, visit our Customer Service Portal for further information.

    * Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.