Lakeland - Winter Haven Holidays

Photo by Lakeland Convention and Visitors Bureau

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Top Flight + Hotel Deals in Lakeland - Winter Haven

Price found within the past 48 hours. Click for updated prices.
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
per person
12 Sept - 15 Sept
found 19 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
8.4/10 Very Good! (1,506 reviews)
Location was good. The sink was totally clogged when we got there but was fixed after we complained. The seal around the toilet was slowly leaking. The shampoo bottle fell off the wall. The bedding was was old and worn. This place could sure use a lot of little updates.

Reviewed on 9 Aug 2025

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
per person
12 Sept - 15 Sept
found 19 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
8.6/10 Excellent! (2,157 reviews)
Bed comfort , great location, friendly staff.

Reviewed on 6 Aug 2025

Siesta Key Palms Resort

Siesta Key Palms Resort

3.5 out of 5
Save 100% on your flight
per person
12 Sept - 15 Sept
found 19 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
9.2/10 Wonderful! (1,004 reviews)
This was a great place to stay. Wonderful tropical vibe in a relaxed atmosphere. Helpful, friendly staff. Very clean room and many unexpected amenities. Lovely experience.

Reviewed on 10 Aug 2025

Luxury Pool Retreat near Siesta Key

Luxury Pool Retreat near Siesta Key

2 out of 5
per person
12 Sept - 15 Sept
found 19 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
10/10 Exceptional! (2 reviews)
Great property. Definitely worth the price

Reviewed on 21 Jul 2025

Beautiful Pool Home Near Siesta Key Beach 2 Bedroom Home

Beautiful Pool Home Near Siesta Key Beach 2 Bedroom Home

3 out of 5
Gulf Gate Estates
per person
12 Sept - 15 Sept
found 19 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
10/10 Exceptional! (1 review)
We have an amazing family time in this beautiful house

Reviewed on 13 May 2025

Where to stay in Lakeland - Winter Haven

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

2 out of top 10 points of interest in this area

If you're spending some time in Downtown Lakeland, Polk Theatre and RP Funding Center are top sights worth seeing.

Find hotels in Downtown Lakeland

Top hotels in Lakeland - Winter Haven

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is €183 per night from 11 Aug to 12 Aug
€183
11 Aug - 12 Aug
includes taxes & fees
7.8/10 Good! (8,284 reviews)
"Amazing stay! The hotel was super clean, staff was friendly and helpful, and the location was perfect for exploring Orlando.The water park was amazing ,my sister had such an amazing time . I’ll definitely be back!"

Reviewed on 9 Aug 2025

The Grove Resort & Water Park Orlando
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is €121 per night from 17 Aug to 18 Aug
€121
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (4,175 reviews)
"Amazing accommodations"

Reviewed on 9 Aug 2025

Hilton Vacation Club Mystic Dunes Orlando
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundable
The price is €138 per night from 12 Aug to 13 Aug
€138
12 Aug - 13 Aug
includes taxes & fees
8.6/10 Excellent! (2,276 reviews)
"Check in took time and not much explained finally found room and key didnt work . Room was immaculate with everything you could possibly need . Fully equipped kitchen . Target opposite and great restaurants along main road abd shopping options ..loved the pools a littke crowded at times . Felt rushed ..."

Reviewed on 6 Aug 2025

Holiday Inn Club Vacations at Orange Lake Resort by IHG
See all 43,517 properties in Lakeland - Winter Haven
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

Legoland Florida featuring a river or creek, a pond and rides

LEGOLAND® Florida

Take the kids to this dynamic theme park for a day full of exciting rides, LEGO® brick creations and the chance to build your own LEGO®robots.

LEGOLAND® Florida
The Circle B Bar Reserve

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.

The Circle B Bar Reserve

Lakeside Village

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.

Lakeside Village

What to do in Lakeland - Winter Haven

Horse Petting

Central Florida Adventure Park - Authentic Dude Ranch Experience

€21
per adult
Central Florida Adventure Park - Authentic Dude Ranch Experience
Sea Screamer boat in Orlando

Day Trip to Clearwater Beach with Sea Screamer Ride

€106
per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
Daytona Beach Day trip with hotel pick ups from Central Florida

Daytona Beach Day trip with hotel pick ups from Central Florida

€82
per adult
Daytona Beach Day trip with hotel pick ups from Central Florida
See all activities in Lakeland - Winter Haven

Frequently asked questions

How much does a Lakeland - Winter Haven holiday package cost?
Custom build your Lakeland - Winter Haven package from as little as €222. Pick from any combination of rental cars, flights and hotels to craft the getaway of your dreams. Don't forget to add on a few experiences or tours!
How do I get a cheap travel package to Lakeland - Winter Haven?
Bundle your hotels and flights with Expedia to save big on your next getaway. With more than 550 airlines and 1,000,000 hotel options worldwide, your Lakeland - Winter Haven holiday package can be tailored exactly to suit your travel style. With all that extra money, why not include a few exciting activities and tours? It's an easy way to unlock even more discounts. That holiday you've always dreamed of in Lakeland - Winter Haven is much closer than you thought!
Where should I stay in Lakeland - Winter Haven?
There's an abundance of excellent places to stay in Lakeland - Winter Haven, including Lakeland. This destination is home to many much-loved attractions including Publix Field at Joker Marchant Stadium and Polk Museum of Art. Another option is to head to Winter Haven, where you'll find LEGOLAND® Florida and Chain of Lakes Park. If you're here for a while, journey to both vibrant cities!
What are the top hotels in Lakeland - Winter Haven?
Days Inn & Suites by Wyndham Lakeland and Hyatt Place Lakeland Centre know how to make their guests feel welcome in Davenport. If you also plan to get to Haines City, have a look at Comfort Inn & Suites Maingate South and Winter Haven Gardens Inn. Both are popular with travellers.
How far in advance should I book my Lakeland - Winter Haven holiday?
Your best bet is to book early. Airlines typically advertise flight tickets nearly 12 months ahead of departure, and this is a great opportunity to pick up some of the cheapest prices. Just been told you need to take some holiday time next month? No sweat. Expedia are never short on fantastic deals to help you have the getaway of your dreams, at an affordable price.
What does an Expedia Lakeland - Winter Haven travel package include?
Rental cars, flights and hotels — we've got them covered. With Expedia, you can shape your Lakeland - Winter Haven package just the way you want. All you have to do is decide what you need. Once you've made your booking, you can add on fun things like experiences and activities. The more you bundle, the more you save!
What should I know before booking a Lakeland - Winter Haven travel package?
An Expedia travel package can be customized for your budget and is an easy way to stretch your dollars further. How much you include is totally up to you. Hotels, rental cars and flights — decide on a combination that suits your style.
Can I choose my airline with a Lakeland - Winter Haven Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the flexibility to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Lakeland - Winter Haven holiday package?
Whether it's your hotel or flight, you can cancel or alter it. Booked your Lakeland - Winter Haven holiday package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may be charged a fee by your airline, hotel or car rental company. For further information, head to our Customer Service Portal. We'll help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.