Cumberland Holidays
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Price found within the past 48 hours. Click for updated prices.
- The Westin Sarasota
Jul 12 - Jul 17The Westin Sarasota + Flight
Central Sarasota5 nights9.0/10 - Wonderful (1,183 reviews)"Beautiful hotel!!"Reviewed May 27, 2026Return • Dublin (DUB) - Tampa (TPA)DUB - TPA • 1 stop TPA - DUB • 1 stop€1,484€1,237found 9 hours agoper traveller - The Residences at Siesta Key Beach by Hyatt Vacation Club
Jul 12 - Jul 17The Residences at Siesta Key Beach by Hyatt Vacation Club + Flight
South Village5 nights9.6/10 - Exceptional (354 reviews)"Amazing place for a family vacation !"Reviewed May 26, 2026Return • Dublin (DUB) - Tampa (TPA)DUB - TPA • 1 stop TPA - DUB • 1 stop€2,976€2,138found 9 hours agoper traveller - Captiva Beach Resort
Jul 12 - Jul 17Captiva Beach Resort + Flight
South Village5 nights9.0/10 - Wonderful (1,259 reviews)"Awesome! Didn’t expect it to be so good! I missed the fact that we will have 2 bathrooms which was such a great surprise! Next time I will grab the slippers though — the floors were cold like in some Mediterranean wine cellar 😅"Reviewed May 28, 2026Return • Dublin (DUB) - Tampa (TPA)DUB - TPA • 1 stop TPA - DUB • 1 stop€1,734€1,404found 6 hours agoper traveller - Tropical Beach Resorts
Jul 12 - Jul 17Tropical Beach Resorts + Flight
South Village5 nights9.4/10 - Exceptional (5,519 reviews)"I was quite impressed how nice and clean the room was and the property in general. Very convenient to the beach and the overall price I think, very comparable to others. The trolley pickups nearby meant I parked the car and didn't have to get it out until we left. Would love to stay again. The beach was beautiful too Cracker Curt restaurant nearby definitely not worth it though so don't make that mistake but to be clear, has nothing to be connected to the resort."Reviewed May 28, 2026Return • Dublin (DUB) - Tampa (TPA)DUB - TPA • 1 stop TPA - DUB • 1 stop€1,716€1,466found 6 hours agoper traveller - Silver Surf Gulf Beach Resort
Jul 12 - Jul 17Silver Surf Gulf Beach Resort + Flight
Bradenton Beach5 nights9.6/10 - Exceptional (1,001 reviews)"What a fabulous place. If you are planning a trip to AMI then I highly recommend that you book this little gem asap. Looks like a motel, but it is so much more than that ... The rooms have been thoughtfully furnished. King size bed is very comfy. The shower is powerful. The fridge is big !! The room was incredibly clean and the staff really seem to care. The facilities are also amazing. Free coffee and breakfast in the mornings. You get 4 beach towels which you can renew every day. ..."Reviewed May 18, 2026Return • Dublin (DUB) - Tampa (TPA)DUB - TPA • 1 stop TPA - DUB • 1 stop€1,843€1,575found 9 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 Wing Chun Kung Fu Downtown Lakeland are top sights worth seeing.
Top hotels in Cumberland
Howard Johnson by Wyndham Lakeland
939 W. Robson St. Lakeland FL
Fully refundableReserve now, pay when you stay
The price is €68 per night from 31 May to 1 Jun
€68
31 May - 1 Jun
includes taxes & fees
7.2/10 Good! (1,365 reviews)
"Awesome Energy at Front Desk. Good stay and decent prices."
Reviewed on 27 May 2026
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
The price is €110 per night from 7 Jun to 8 Jun
€110
7 Jun - 8 Jun
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Clean room and helpful friendly staff. I already booked here again."
Reviewed on 28 May 2026
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
The price is €514 per night from 19 Jun to 20 Jun
€514
19 Jun - 20 Jun
includes taxes & fees
8.8/10 Excellent! (125 reviews)
"There were sooo many activities in the evening for the kids. Next time we’ll have to stay longer."
Reviewed on 28 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
Lakeside Village
4/5(1 review)
You can find the perfect gifts to bring home at Lakeside Village during your visit to Lakeland. Amble around the area's lakeside or attend a sporting event.
The Circle B Bar Reserve
Explore the great outdoors at The Circle B Bar Reserve, a lovely green space in Lakeland. Visit the shops and top-notch restaurants in this family-friendly area.
Florida Air Museum
You can spend an afternoon browsing the exhibits at Florida Air Museum during your travels in Lakeland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Things to do
Winter Haven: Coffee, Tea & Dessert Food Tour
€115
per adult
Winter Haven: Guided Brunch Tour with Local Delicacies
€124
per adult
Winter Haven: Chef's Table and Wine Tasting Tour
€230
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.