Cheap Vacations in Lakeland - Winter Haven

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Lakeland - Winter Haven vacations

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flightPrice was $713, price is now $483 per person
per person
Jul 23 - Jul 29
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar

3 out of 5
Belle Vista
Save 100% on your flightPrice was $1,873, price is now $1,305 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Price was $698, price is now $503 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Innisbrook, A Salamander Golf & Spa Resort

Innisbrook, A Salamander Golf & Spa Resort

3.5 out of 5
Save 100% on your flightPrice was $930, price is now $696 per person
per person
Jul 23 - Jul 29
Roundtrip flight included
New York (JFK) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Price was $885, price is now $695 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Belle Vista
Price was $941, price is now $741 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Silver Sands

Silver Sands

3.5 out of 5
Price was $718, price is now $577 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
The Inn on Third

The Inn on Third

2 out of 5
Downtown St. Petersburg
Price was $640, price is now $519 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Siesta Key Village
Save 100% on your flightPrice was $1,379, price is now $1,130 per person
per person
Jul 16 - Jul 22
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Price was $845, price is now $694 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)

3-night Lakeland - Winter Haven vacations

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Price was $567, price is now $423 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Price was $885, price is now $695 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Silver Sands

Silver Sands

3.5 out of 5
Price was $615, price is now $498 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Price was $744, price is now $627 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Price was $630, price is now $535 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Shephard's Beach Resort

Shephard's Beach Resort

3.5 out of 5
Price was $673, price is now $576 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Hotel Haya

Hotel Haya

4 out of 5
Price was $603, price is now $518 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Price was $869, price is now $755 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Price was $1,365, price is now $1,194 per person
per person
Jul 14 - Jul 17
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
ROOST Tampa

ROOST Tampa

4.5 out of 5
Price was $766, price is now $671 per person
per person
Jul 23 - Jul 26
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Price was $472, price is now $415 per person
per person
Jul 27 - Jul 30
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Holiday Inn Tampa North, an IHG Hotel

Holiday Inn Tampa North, an IHG Hotel

3 out of 5
Price was $473, price is now $416 per person
per person
Jul 7 - Jul 10
Roundtrip flight included
New York (JFK) to Tampa (TPA)

4-night Lakeland - Winter Haven vacations

The Godfrey Hotel & Cabanas Tampa

The Godfrey Hotel & Cabanas Tampa

3.5 out of 5
Price was $521, price is now $433 per person
per person
Jul 27 - Jul 31
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Price was $707, price is now $606 per person
per person
Jul 27 - Jul 31
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Price was $698, price is now $503 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Price was $741, price is now $559 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Silver Sands

Silver Sands

3.5 out of 5
Price was $718, price is now $577 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
The Inn on Third

The Inn on Third

2 out of 5
Price was $640, price is now $519 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Price was $845, price is now $694 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Price was $962, price is now $791 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Shephard's Beach Resort

Shephard's Beach Resort

3.5 out of 5
Price was $924, price is now $765 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Hotel Haya

Hotel Haya

4 out of 5
Price was $825, price is now $684 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Hotel Cabana Clearwater Beach

Hotel Cabana Clearwater Beach

3 out of 5
Price was $773, price is now $646 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Holiday Inn Tampa North, an IHG Hotel

Holiday Inn Tampa North, an IHG Hotel

3 out of 5
Price was $673, price is now $576 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Denver (DEN) to Tampa (TPA)

5-night Lakeland - Winter Haven vacations

The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flightPrice was $1,641, price is now $1,070 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar

3 out of 5
Save 100% on your flightPrice was $1,873, price is now $1,305 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Price was $1,392, price is now $1,067 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Price was $941, price is now $741 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Price was $1,644, price is now $1,325 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Price was $1,621, price is now $1,338 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Barefoot Beach Club

Barefoot Beach Club

2.5 out of 5
Price was $1,903, price is now $1,611 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Price was $970, price is now $822 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Dolphin Beach Resort

Dolphin Beach Resort

3 out of 5
Price was $715, price is now $611 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Price was $1,152, price is now $992 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Price was $2,734, price is now $2,380 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)
Postcard Inn On The Beach

Postcard Inn On The Beach

3 out of 5
Price was $616, price is now $538 per person
per person
Jul 26 - Jul 31
Roundtrip flight included
Denver (DEN) to Tampa (TPA)

6-7 night Lakeland - Winter Haven vacations

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Save 100% on your flightPrice was $713, price is now $483 per person
per person
Jul 23 - Jul 29
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Save 100% on your flightPrice was $782, price is now $538 per person
per person
Jul 23 - Jul 29
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Innisbrook, A Salamander Golf & Spa Resort

Innisbrook, A Salamander Golf & Spa Resort

3.5 out of 5
Save 100% on your flightPrice was $930, price is now $696 per person
per person
Jul 23 - Jul 29
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Price was $1,564, price is now $1,267 per person
per person
Jul 14 - Jul 21
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flightPrice was $1,379, price is now $1,130 per person
per person
Jul 16 - Jul 22
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Price was $1,316, price is now $1,091 per person
per person
Jul 14 - Jul 21
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flightPrice was $1,245, price is now $1,033 per person
per person
Jul 16 - Jul 22
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Hotel Cabana Clearwater Beach

Hotel Cabana Clearwater Beach

3 out of 5
Price was $929, price is now $778 per person
per person
Jul 14 - Jul 21
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Price was $1,202, price is now $1,013 per person
per person
Jul 16 - Jul 22
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Siesta Key Palms Resort

Siesta Key Palms Resort

3.5 out of 5
Price was $728, price is now $614 per person
per person
Jul 16 - Jul 22
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Shephard's Beach Resort

Shephard's Beach Resort

3.5 out of 5
Price was $1,140, price is now $965 per person
per person
Jul 14 - Jul 21
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Dolphin Beach Resort

Dolphin Beach Resort

3 out of 5
Price was $717, price is now $611 per person
per person
Jul 23 - Jul 29
Roundtrip flight included
New York (JFK) to Tampa (TPA)

Lakeland - Winter Haven Vacation Deal FAQ's

Where to find Lakeland - Winter Haven package deals?

On CheapTickets, you can find package deals in Lakeland - Winter Haven and save up to $287.

When is peak season in Lakeland - Winter Haven?

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When is the best time to visit Lakeland - Winter Haven?

If you're looking for cheap vacations to Lakeland - Winter Haven, is the best time to visit Lakeland - Winter Haven.

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Prices for Lakeland - Winter Haven vacations can peak during .

When is low season in Lakeland - Winter Haven?

We have found to be the least-crowded time of the year to visit Lakeland - Winter Haven.

Flight deals to Lakeland - Winter Haven

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Jun 28
SJU
San Juan
TPA
Tampa
$71 One way, found 12 hours ago
$71
One way
found 12 hours ago
Select Spirit Airlines flight, departing Wed, Jun 28 from San Juan to Tampa, priced at $71 found 12 hours ago
Tue, Jun 6
SJU
San Juan
MCO
Orlando
$88 One way, found 11 hours ago
$88
One way
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Jun 6 from San Juan to Orlando, priced at $88 found 11 hours ago
Sun, Jun 4
SEA
Seattle
TPA
Tampa
$100 One way, found 3 days ago
$100
One way
found 3 days ago
Select Frontier Airlines flight, departing Sun, Jun 4 from Seattle to Tampa, priced at $100 found 3 days ago
Sat, Jul 1 - Fri, Jul 7
SJU
San Juan
TPA
Tampa
$141 Roundtrip, found 12 hours ago
$141
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Sat, Jul 1 from San Juan to Tampa, returning Fri, Jul 7, priced at $141 found 12 hours ago
Tue, Sep 12 - Wed, Sep 13
SJU
San Juan
MCO
Orlando
$163 Roundtrip, found 1 hour ago
$163
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Sep 12 from San Juan to Orlando, returning Wed, Sep 13, priced at $163 found 1 hour ago
Thu, Jun 8 - Mon, Jun 19
SEA
Seattle
TPA
Tampa
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Jun 8 from Seattle to Tampa, returning Mon, Jun 19, priced at $208 found 3 days ago

Top rated hotels for your Lakeland - Winter Haven vacation

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Free Cancellation
Reserve now, pay when you stay
34.52 mi from city center
The price is $192 per night
$192
per night
Jun 4 - Jun 5
Located in Winter Garden, The Grove Resort & Water Park Orlando is on a lake, a 1-minute drive from Surfari Water Park and 11 minutes from Orange County National Golf Club.
Margaritaville Resort Orlando

Margaritaville Resort Orlando

4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
33.56 mi from city center
The price is $179 per night
$179
per night
Jun 5 - Jun 6
With a stay at Margaritaville Resort Orlando in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Disney's Hollywood Studios®.
Sonder Cirrus

Sonder Cirrus

3.5 out of 5
7888 West Irlo Bronson Memorial Highway, Kissimmee, FL
33.59 mi from city center
The price is $105 per night
$105
per night
Jun 7 - Jun 8
With a stay at Sonder Cirrus in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town.
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.