Lakeland - Winter Haven Vacation Packages

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Your Lakeland - Winter Haven Vacation

With everything organized before you go, our Lakeland - Winter Haven vacation packages let you focus on having fun. Known for its golfing, walking trails and family-friendly attractions, the only thing left to do is kick back and enjoy every unforgettable moment. Kick off your trip to Lakeland - Winter Haven with a few nights in Lakeland visiting popular sights like RP Funding Centre and Lakeside Village. Davenport is another city that draws travellers from far and wide. Reunion Resort Golf Course and Southern Dunes Golf and Country Club are two of the top places to see here. When it's time to stop dreaming and start packing, Expedia will help turn your Lakeland - Winter Haven vacation into a reality.

Top Lakeland - Winter Haven Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Clearwater Suites

Clearwater Suites

2.5 out of 5
Price was CA $718, price is now CA $426 per person
CA $426
per person
Oct 2 - Oct 5
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.8/10 Excellent! (19 reviews)
Estuvimos dos noches en el hotel y nos gustó mucho, todo muy limpio lo mismo dentro de la habitación que en la piscina, la atención excelente, la playa super serca del hotel es solo cruzar la calle, está ubicado céntrico, una experiencia satisfactoria la esatacia, lo volvería a repetir!!!

Reviewed on Aug. 31, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,189, price is now CA $1,176 per person
CA $1,176
per person
Oct 16 - Oct 21
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (445 reviews)
Excellent place no word to explain how perfect everything was. We definitely go there from now on

Reviewed on Aug. 24, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was CA $1,112, price is now CA $600 per person
CA $600
per person
Oct 2 - Oct 5
found 14 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (609 reviews)
Loved the condo, the access to the beach, in unit laundry, and convenience of the location. Gym and beach bar on site, would definitely come back!

Reviewed on Aug. 30, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $1,568, price is now CA $846 per person
CA $846
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,053 reviews)
The room was fantastic with a big wrap around balcony. Even though the weather did not cooperate, we all enjoyed chilling on the balcony with many trips to the pool. Beach was great. My only disappointment was they did not have any type of grill anywhere. I brought some really expensive steaks, burgers,hot dogs, which we had to cook in a pan. The staff was fantastic and made sure we had everything we needed

Reviewed on Aug. 24, 2025

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Price was CA $1,865, price is now CA $1,114 per person
CA $1,114
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (467 reviews)
The staff were the best part of the property. It wasn't super convenient to go to the main office for anything because of having to cross a busy road and walking a block and parking was limited so we couldn't park there to use the pool or amenities. The room itself was clean and we appreciated the view on the bay but the bed wasn't comfortable at all. Overall, it was a decent value but the office being so far offsite with the better pool, beach access and bar but no parking for guests of the other hotels was a real detractor for us.

Reviewed on Aug. 27, 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
5/5(1 area review)

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

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Lakeland - Winter Haven Hotel Deals

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 CA $205 per night from Sep 2 to Sep 3
CA $205
CA $292 total
Sep 2 - Sep 3
includes taxes & fees
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 CA $130 per night from Sep 21 to Sep 22
CA $130
CA $194 total
Sep 21 - Sep 22
includes taxes & fees
Hilton Vacation Club Mystic Dunes Orlando
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Sep 28 to Sep 29
CA $167
CA $258 total
Sep 28 - Sep 29
includes taxes & fees
Margaritaville Resort Orlando with H2O Waterpark
See all 44,755 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Lakeland - Winter Haven

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

LEGOLAND® Florida

4.5/5(72 reviews)

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
Dinosaur World Museum

Dinosaur World

5/5(1 review)

With more than 200 life-size dinosaur models and many interactive games and activities, this educational theme park is great for families.

Dinosaur World
Camp Mack's River Resort Airboat Rides

Camp Mack's River Resort Airboat Rides

Enjoy an outing to Camp Mack's River Resort Airboat Rides during your stay in Lake Wales. Wander the lakeside and gardens in this family-friendly area.

Camp Mack's River Resort Airboat Rides

What to do in Lakeland - Winter Haven

Playground

Dinosaur World Theme Park

CA $37
per adult
Dinosaur World Theme Park
Picture 2 for Activity Tampa: Haunted Train Depot Ghost Adventure

Tampa Bay Area: VIP Haunted Train Depot Ghost Adventure

CA $73
per adult
Tampa Bay Area: VIP Haunted Train Depot Ghost Adventure
Sea Screamer boat in Orlando

Day Trip to Clearwater Beach with Sea Screamer Ride

CA $164
per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
See all activities in Lakeland - Winter Haven

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