Cumberland Holidays
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Price found within the past 48 hours. Click for updated prices.
- Westgate Town Center Resort
Jul 20 - Jul 30Westgate Town Center Resort + Flight
Kissimmee10 nights8.2/10 - Very good (1,750 reviews)"Es super increíble me encantó"Reviewed May 31, 2026Return • London (LCY) - Orlando (MCO)LCY - MCO • 2 stops MCO - LHR • 2 stops - Palazzo Lakeside Hotel
Jul 4 - Jul 11Palazzo Lakeside Hotel + Flight
Kissimmee7 nights8.2/10 - Very good (5,173 reviews)"Buen hotel, muy buen desayuno, excelente ubicación."Reviewed May 31, 2026Return • Edinburgh (EDI) - Orlando (MCO)EDI - MCO • Direct MCO - EDI • Direct£1,919£961found 21 hours agoper traveller - Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Aug 5 - Aug 18Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight
International Drive District13 nights7.8/10 - Good (501 reviews)"Air conditioner was extremely loud and made it hard to sleep with it on. Too humid with it off. TVs do not have any streaming capability. General room size and layout was nice, lots of storage. No gym unless you upgrade your room to a suite, but honestly the gym was not worthwhile anyway if you like to lift. A single cable machine and no dumbbells. Breakfast was just okay. Hard boiled eggs yogurt cereal bread etc. located next to a 24 hr arcade but we didn’t hear any noise from our room at..."Reviewed May 27, 2026Return • London (LHR) - Orlando (MCO)LHR - MCO • 1 stop MCO - LHR • 1 stop - Westgate Blue Tree Resort in Lake Buena Vista
Aug 15 - Aug 29Westgate Blue Tree Resort in Lake Buena Vista + Flight
Orlando14 nights8.6/10 - Excellent (1,002 reviews)"Great place to stay close to the parks! We stay there every time we visit Orlando, which is at least 3-4 times a year! Comfortable apartments, clean and well taken care of."Reviewed May 27, 2026Return • London (LHR) - Orlando (MCO)LHR - MCO • 2 stops MCO - LHR • 2 stops - Westgate Towers Resort
Jun 30 - Jul 11Westgate Towers Resort + Flight
Kissimmee11 nights8.6/10 - Excellent (1,006 reviews)"Good"Reviewed May 31, 2026Return • London (LHR) - Orlando (MCO)LHR - MCO • Direct MCO - LHR • Direct£1,546£965found 10 hours agoper traveller
Where to stay in Cumberland
Find the best Cumberland areas and neighborhoods for the activities you enjoy most. Learn more about Cumberland
Downtown Lakeland
2 out of top 10 points of interest in this area
If you're spending some time in Downtown Lakeland, RP Funding Center and Lake Mirror are top sights worth seeing.
Top hotels in Cumberland
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
The price is £95 per night from 7 Jun to 8 Jun
£95
7 Jun - 8 Jun
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"What a great place and location"
Reviewed on 30 May 2026
Days Inn & Suites by Wyndham Lakeland
4502 N Socrum Loop Rd Lakeland FL
Fully refundableReserve now, pay when you stay
The price is £64 per night from 25 Jun to 26 Jun
£64
25 Jun - 26 Jun
includes taxes & fees
8.6/10 Excellent! (336 reviews)
"Love it"
Reviewed on 30 May 2026
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
The price is £353 per night from 21 Jun to 22 Jun
£353
21 Jun - 22 Jun
includes taxes & fees
8.8/10 Excellent! (126 reviews)
"the room was smelling like pee and the pool was dirty also the fridge wasn’t working"
Reviewed on 31 May 2026
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.
Popular places to visit
Sun N Fun Air Museum
You can spend time exploring the galleries in Sun N Fun Air Museum in Lakeland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Family Fun Center
Enjoy an outing to Family Fun Center during your stay in Lakeland. Amble around the area's lakeside or attend a sporting event.
Eastside Village Shopping Center
You can browse for the perfect souvenirs at Eastside Village Shopping Center during your trip to Lakeland. Amble around this family-friendly area's lakeside or attend a sporting event.
Things to do
Ladies Luncheon Pontoon Tour (Gentleman welcome)
£73
per adult
Winter Haven: Coffee, Tea & Dessert Food Tour
£98
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.