Cheap Vacations in Lakeland - Winter Haven

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Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Save 100% on your flight
Price was $1,576, price is now $1,087 per person
$1,087
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

3-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $526, price is now $397 per person
$397
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $926, price is now $595 per person
$595
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,294, price is now $875 per person
$875
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,030, price is now $707 per person
$707
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,160, price is now $801 per person
$801
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
Price was $913, price is now $639 per person
$639
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $839, price is now $593 per person
$593
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $956, price is now $678 per person
$678
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,760, price is now $1,271 per person
$1,271
per person
Jul 26 - Jul 29
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $812, price is now $593 per person
$593
per person
Jul 21 - Jul 24
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
Price was $1,190, price is now $871 per person
$871
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $648, price is now $485 per person
$485
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

4-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $779, price is now $498 per person
$498
per person
Jul 30 - Aug 3
found 6 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,328, price is now $815 per person
$815
per person
Jul 30 - Aug 3
found 5 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $775, price is now $518 per person
$518
per person
Jul 30 - Aug 3
found 6 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,484, price is now $1,004 per person
$1,004
per person
Jul 30 - Aug 3
found 5 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,995, price is now $1,352 per person
$1,352
per person
Jul 30 - Aug 3
found 5 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,190, price is now $810 per person
$810
per person
Jul 30 - Aug 3
found 6 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $975, price is now $701 per person
$701
per person
Jul 30 - Aug 3
found 6 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
Price was $1,253, price is now $909 per person
$909
per person
Jul 30 - Aug 3
found 6 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Price was $973, price is now $706 per person
$706
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Price was $978, price is now $713 per person
$713
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $3,056, price is now $2,235 per person
$2,235
per person
Jul 30 - Aug 3
found 6 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Inn on the Beach

Inn on the Beach

2.5 out of 5
Save 100% on your flight
Price was $963, price is now $707 per person
$707
per person
Jul 30 - Aug 3
found 4 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)

5-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $887, price is now $589 per person
$589
per person
Jul 30 - Aug 4
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,540, price is now $989 per person
$989
per person
Jul 20 - Jul 25
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,507, price is now $1,017 per person
$1,017
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Luce, St. Pete Beach, a Tribute Portfolio Hotel

The Luce, St. Pete Beach, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $1,296, price is now $884 per person
$884
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Save 100% on your flight
Price was $1,576, price is now $1,087 per person
$1,087
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $879, price is now $607 per person
$607
per person
Jul 30 - Aug 4
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Via Roma Beach Resort

Via Roma Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,330, price is now $924 per person
$924
per person
Aug 9 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Memphis (MEM) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,113, price is now $778 per person
$778
per person
Jul 30 - Aug 4
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,857, price is now $1,310 per person
$1,310
per person
Jul 20 - Jul 25
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Inn on the Beach

Inn on the Beach

2.5 out of 5
Save 100% on your flight
Price was $1,662, price is now $1,174 per person
$1,174
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,306, price is now $1,640 per person
$1,640
per person
Jul 20 - Jul 25
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $1,197, price is now $858 per person
$858
per person
Jul 30 - Aug 4
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

6-7 night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $949, price is now $535 per person
$535
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $2,169, price is now $1,208 per person
$1,208
per person
Jul 19 - Jul 26
found 20 hours ago
Roundtrip flight included
Indianapolis (IND) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $2,145, price is now $1,340 per person
$1,340
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,699, price is now $1,099 per person
$1,099
per person
Aug 1 - Aug 8
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Luce, St. Pete Beach, a Tribute Portfolio Hotel

The Luce, St. Pete Beach, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $1,575, price is now $1,031 per person
$1,031
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $3,270, price is now $2,142 per person
$2,142
per person
Jul 19 - Jul 26
found 20 hours ago
Roundtrip flight included
Indianapolis (IND) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,471, price is now $969 per person
$969
per person
Jul 19 - Jul 26
found 20 hours ago
Roundtrip flight included
Indianapolis (IND) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $2,572, price is now $1,702 per person
$1,702
per person
Jul 19 - Jul 26
found 20 hours ago
Roundtrip flight included
Indianapolis (IND) to Tampa (TPA)
Oasis Palms

Oasis Palms

2 out of 5
Save 100% on your flight
Price was $1,057, price is now $703 per person
$703
per person
Jul 16 - Jul 23
found 17 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $4,593, price is now $3,092 per person
$3,092
per person
Aug 1 - Aug 8
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $2,123, price is now $1,445 per person
$1,445
per person
Jul 19 - Jul 26
found 20 hours ago
Roundtrip flight included
Indianapolis (IND) to Tampa (TPA)
The Roth Hotel

The Roth Hotel

2 out of 5
Save 100% on your flight
Price was $1,330, price is now $927 per person
$927
per person
Jul 16 - Jul 23
found 17 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)

Flight deals to Lakeland - Winter Haven

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

Mon, Aug 17 - Thu, Aug 20
SJU
San Juan
MCO
Orlando
$180 Roundtrip, found 1 hour ago
$180
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Aug 17 from San Juan to Orlando, returning Thu, Aug 20, priced at $180 found 1 hour ago
Fri, Sep 18 - Mon, Sep 21
SJU
San Juan
TPA
Tampa
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Sep 18 from San Juan to Tampa, returning Mon, Sep 21, priced at $188 found 2 days ago
Thu, Aug 20 - Mon, Aug 24
SEA
Seattle
MCO
Orlando
$287 Roundtrip, found 6 days ago
$287
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Thu, Aug 20 from Seattle to Orlando, returning Mon, Aug 24, priced at $287 found 6 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
34.59 mi from city center
$248 nightly
The price is $279 total per night
$279 total
Jun 22 - Jun 23
Total with taxes and fees
Located in Four Corners, 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.
Pool
Hot Tub
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
33.51 mi from city center
$198 nightly
The price is $225 total per night
$225 total
Jun 22 - Jun 23
Total with taxes and fees
Located in Kissimmee, Margaritaville Resort Orlando with H2O Waterpark is a 1-minute drive from Island H2O Live! and 8 minutes from Walt Disney World® Resort.
Pool
Hot Tub
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
Free Cancellation
34.22 mi from city center
$171 nightly
The price is $192 total per night
$192 total
Jun 22 - Jun 23
Total with taxes and fees
Located in Kissimmee (Orange Lake), Holiday Inn Club Vacations at Orange Lake Resort by IHG is within a 15-minute drive of Old Town and Disney's Animal Kingdom® Theme Park.
Pool
Hot Tub
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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 Picks

^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.