Lakeland - Winter Haven Vacation Packages for 2026

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Lakeland - Winter Haven Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Oasis Palms

Oasis Palms

Sunshine Beach
Save 100% on your flight
$581
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Stay at this hotel in Treasure Island. Enjoy free WiFi, free parking, and a picnic area. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Kimie, the property manager was awesome! She went above and beyond to make sure we were comfortable and well taken care of during the stay.

Reviewed on Aug 17, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
Save 100% on your flight
$852
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
$1,515
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and Manatee Public Beach are located nearby.
Captiva Beach Resort

Captiva Beach Resort

South Village
Save 100% on your flight
$906
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Room super clean, we love it. Parking ok Kitchen ok Staff, was ok, But we have some comments that may be helpful to the property. 1 - We had problems with the door lock, the staff should be able to show how it works, or give better instructions on the welcome paperwork. 2 - We asked if there was a restroom we could use after checkout, the lady(front desk) said: NO. Only a change room. And we found out that the property have a restroom outside, close to the change room. Since we decided to stay a bit longer at the beach on Sunday the restroom would help us a lot before take 3 hours driving to final destination. She could tell us about the restroom, but she did not. Everything else was excelent! Location, quite place, clean and very confortable. Thank you.

Reviewed on Aug 21, 2026

Crystal Palms Beach Resort

Crystal Palms Beach Resort

Sunshine Beach
Save 100% on your flight
$694
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy a 24-hour front desk, dry cleaning or laundry services, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
We have been visiting this property for over 15 years and had a few worries when reading the feedback regarding the refurbishment. We have recently stayed for a 3 week holiday and can honestly say it has been the best experience we have had, from check in to check out everything was very smooth and we had no problems what so ever. The cleanliness of our unit was much better than we have seen in recent years. It seems that the new management have really put time and effort into the property. Thank you for a wonderful stay and we will be back soon.

Reviewed on Aug 22, 2026

Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key

$720
per person
Nov 2 - Nov 9
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Turtle Beach are located nearby.
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Lakeland - Winter Haven Vacation Packages

Trying to figure out a way to bundle your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We're here to book everything you'll need to make your Lakeland - Winter Haven trip one to remember. Our Travel Center is a one-stop shop where you can put together the best Lakeland - Winter Haven vacation package for you. AARP Travel Center has an amazing list of flights and hotels, and local endeavors to choose from.

Lakeland - Winter Haven Hotels

You can choose from around 44924 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Lakeland - Winter Haven hot spots, we have plenty of options available.

We have fantastic rates on everything from family-friendly resorts that check off all the vacation must-haves to affordable hotels perfect for those on a budget. You can scan our vast catalog of options and select the hotel that is ideal for you and your family. With AARP Travel Center's Lakeland - Winter Haven hotel packages, you not only get a great rate on your flight, but also a great place to stay.

Things to do in Lakeland - Winter Haven

The fact that you are going to Lakeland - Winter Haven means your vacation is already off to a fabulous start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.

If you need more suggestions, then make sure to click on AARP's "Things to Do" page.

Save with a Lakeland - Winter Haven Vacation Package

As an AARP Member, you can benefit from all the great deals. You'll save on select hotels worldwide, flights, and rental cars. No matter what vacation package you select, you can rest easy knowing that you already saved on your trip. The hardest packing you'll have to do is for your suitcase. Bundle today and get ready for your Lakeland - Winter Haven vacation.

Top Hotel Deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL
55.7 km from city center
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL
53.96 km from city center
Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL
55.11 km from city center
Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL
51.49 km from city center
Book a stay at this golf hotel in Kissimmee. Enjoy free WiFi, 4 outdoor pools, and a golf course. Our guests praise the pool and the restaurant in our reviews. ...
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL
16.09 km from city center
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful ...
Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate

1500 Masters Blvd Davenport FL
44.94 km from city center
Book a stay at this spa hotel in Four Corners. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd Winter Garden FL
54.47 km from city center
Book a stay at this family-friendly hotel in Four Corners. Enjoy free WiFi, 2 outdoor pools, and free water park access. Our guests praise the pool and the helpful ...
Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

3151 Sunset Walk Drive Kissimmee FL
53.84 km from city center
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and room service. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood ...
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

8000 Fins Up Circle Kissimmee FL
54.49 km from city center
Book a stay at this spa aparthotel in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Westgate Town Center Resort

Westgate Town Center Resort

7700 Westgate Blvd. Kissimmee FL
52.8 km from city center
Book a stay at this family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean ...
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

7700 Westgate Blvd. Kissimmee FL
52.84 km from city center
Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the ...
Meliá Orlando Celebration

Meliá Orlando Celebration

225 Celebration Pl Celebration FL
54.36 km from city center
Book a stay at this spa hotel in Celebration. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the pool and the restaurant in our reviews. ...
Quality Inn & Suites By the Parks

Quality Inn & Suites By the Parks

2945 Entry Point Blvd Kissimmee FL
53.42 km from city center
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Berkley, Orlando

The Berkley, Orlando

8545 W. Irlo Bronson Highway Kissimmee FL
54.38 km from city center
Book a stay at this family-friendly aparthotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the ...
Summer Bay Orlando MOD Collection by Sonesta

Summer Bay Orlando MOD Collection by Sonesta

17805 US Highway 192 Clermont FL
54.06 km from city center
Book a stay at this family-friendly hotel in Four Corners. Enjoy free parking, 5 outdoor pools, and 4 hot tubs. Our guests praise the pool and the helpful staff ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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