Cumberland Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Reception
    Aug 8 - Aug 15

    Seasons Florida Resort + Flight

    Kissimmee
    7 nights
    2.0 star property
    9.0/10 - Wonderful (3,583 reviews)
    "First time staying here but was impressed by how quiet it was and the cleanliness of the room. Was only there one night but we would definitely stay there again."
    Reviewed May 27, 2026
    Roundtrip • Tokyo (HND) - Orlando (MCO)
    HND - MCO • 1 stop MCO - HND • 1 stop
    ￥404,534
    ￥341,430
    per traveler
    found 1 day ago
    Seasons Florida Resort
  • Superior House, Resort View | Children's area
    Aug 8 - Aug 15

    Mission to Mars + Flight

    Loughman
    7 nights
    4.0 star property
    Roundtrip • Tokyo (HND) - Orlando (MCO)
    HND - MCO • 1 stop MCO - HND • 1 stop
    Save 100% on your flight
    ￥2,274,250
    ￥1,371,490
    per traveler
    found 1 day ago
    Mission to Mars
  • Aerial view
    Aug 8 - Aug 15

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    7 nights
    4.0 star property
    9.2/10 - Wonderful (1,003 reviews)
    "Everything was excellent, except the pool definitely needed maintenance and cleaning."
    Reviewed May 26, 2026
    Roundtrip • Tokyo (HND) - Orlando (MCO)
    HND - MCO • 1 stop MCO - HND • 1 stop
    ￥641,608
    ￥453,812
    per traveler
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • Water park
    Jun 26 - Jul 1

    Westgate Lakes Resort & Spa Universal Studios Area + Flight

    Orlando
    5 nights
    4.0 star property
    8.4/10 - Very Good (6,450 reviews)
    "The hotel is poorly designed, it’s hard to get around. We had to cross pools to get to the lobby or else walk around multiple buildings. It’s very big but only has one restaurant on site with limited choices. There is no water refilling stations, you must purchase water. The pools are small and very busy, not much staff onsite to help."
    Reviewed May 27, 2026
    Roundtrip • Tokyo (HND) - Orlando (MCO)
    HND - MCO • 1 stop MCO - HND • 1 stop
    ￥442,668
    ￥356,035
    per traveler
    found 1 day ago
    Westgate Lakes Resort & Spa Universal Studios Area
  • Terrace/patio
    Jun 26 - Jul 1

    The Delaney Hotel + Flight

    South Orange
    5 nights
    3.5 star property
    9.6/10 - Exceptional (1,110 reviews)
    "My stay at The Delaney was amazing. Everyone was so kind. I will also like to mention how pleasurable it is to hear a staff member mention to another guest how much they enjoyed working there. I will definitely book again."
    Reviewed May 26, 2026
    Roundtrip • Tokyo (HND) - Orlando (MCO)
    HND - MCO • 1 stop MCO - HND • 1 stop
    ￥417,594
    ￥358,137
    per traveler
    found 1 day ago
    The Delaney Hotel

Where to stay in Cumberland

Find the best Cumberland areas and neighborhoods for the activities you enjoy most. Learn more about Cumberland
Downtown Lakeland

Downtown Lakeland

2 out of top 10 points of interest in this area
4.5/5(103 area reviews)

If you're spending some time in Downtown Lakeland, RP Funding Center and Wing Chun Kung Fu Downtown Lakeland are top sights worth seeing.

Find hotels in Downtown Lakeland

Cumberland Hotel Deals

Howard Johnson by Wyndham Lakeland

Howard Johnson by Wyndham Lakeland

2.5 out of 5
939 W. Robson St. Lakeland FL
Fully refundableReserve now, pay when you stay
The price is ￥10,153 per night from Jun 24 to Jun 25
￥10,153
￥11,371 total
Jun 24 - Jun 25
includes taxes & fees
7/10 Good! (1,361 reviews)
"The room was clean staff was very nice."

Reviewed on May 23, 2026

Howard Johnson by Wyndham Lakeland
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
The price is ￥18,156 per night from Jun 7 to Jun 8
￥18,156
￥20,335 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Good Overall"

Reviewed on May 20, 2026

Holiday Inn Winter Haven by IHG
Days Inn & Suites by Wyndham Lakeland

Days Inn & Suites by Wyndham Lakeland

2.5 out of 5
4502 N Socrum Loop Rd Lakeland FL
Fully refundableReserve now, pay when you stay
The price is ￥11,897 per night from May 31 to Jun 1
￥11,897
￥14,752 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (331 reviews)
"Although the breakfast can be better. Everything else was fine."

Reviewed on May 26, 2026

Days Inn & Suites by Wyndham Lakeland
See all 872 properties in Cumberland
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.

Things to do

Winter Haven: Guided Brunch Tour with Local Delicacies

Winter Haven: Guided Brunch Tour with Local Delicacies

￥22,496
per adult
Winter Haven: Guided Brunch Tour with Local Delicacies
Winter Haven: Chef's Table and Wine Tasting Tour

Winter Haven: Chef's Table and Wine Tasting Tour

￥41,971
per adult
Winter Haven: Chef's Table and Wine Tasting Tour
See all activities in Lakeland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.