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.
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $615, price is now $451 per person
$451
per person
Nov 7 - Nov 11
found 10 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,727, price is now $1,035 per person
$1,035
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,114, price is now $750 per person
$750
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Price was $1,029, price is now $706 per person
$706
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,169, price is now $816 per person
$816
per person
Nov 25 - Nov 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Resort Sixty-Six

Resort Sixty-Six

2.5 out of 5
Price was $1,768, price is now $1,258 per person
$1,258
per person
Nov 21 - Nov 28
found 1 hour ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $1,362, price is now $975 per person
$975
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $2,632, price is now $1,887 per person
$1,887
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $642, price is now $464 per person
$464
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,152, price is now $836 per person
$836
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

3-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Price was $617, price is now $482 per person
$482
per person
Nov 11 - Nov 14
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,567, price is now $1,123 per person
$1,123
per person
Nov 19 - Nov 22
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,093, price is now $788 per person
$788
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $929, price is now $685 per person
$685
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Price was $816, price is now $605 per person
$605
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Price was $797, price is now $592 per person
$592
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $833, price is now $619 per person
$619
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was $828, price is now $640 per person
$640
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Save 100% on your flight
Price was $3,704, price is now $2,870 per person
$2,870
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $714, price is now $557 per person
$557
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Price was $894, price is now $698 per person
$698
per person
Nov 12 - Nov 15
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $711, price is now $556 per person
$556
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)

4-night Lakeland - Winter Haven vacations

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

Oasis Palms

2 out of 5
Price was $507, price is now $382 per person
$382
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,565, price is now $982 per person
$982
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $910, price is now $616 per person
$616
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $759, price is now $524 per person
$524
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Save 100% on your flight
Price was $656, price is now $457 per person
$457
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,237, price is now $867 per person
$867
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $934, price is now $658 per person
$658
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,087, price is now $790 per person
$790
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $615, price is now $451 per person
$451
per person
Nov 7 - Nov 11
found 10 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Price was $1,034, price is now $773 per person
$773
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $2,896, price is now $2,170 per person
$2,170
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $535, price is now $403 per person
$403
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

5-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $642, price is now $464 per person
$464
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,727, price is now $1,035 per person
$1,035
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,114, price is now $750 per person
$750
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Roth Hotel

The Roth Hotel

2 out of 5
Save 100% on your flight
Price was $944, price is now $668 per person
$668
per person
Nov 26 - Dec 1
found 15 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,016, price is now $725 per person
$725
per person
Nov 26 - Dec 1
found 15 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $711, price is now $507 per person
$507
per person
Nov 26 - Dec 1
found 15 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $1,362, price is now $975 per person
$975
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $2,632, price is now $1,887 per person
$1,887
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Save 100% on your flight
Price was $793, price is now $570 per person
$570
per person
Nov 26 - Dec 1
found 15 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Price was $1,759, price is now $1,265 per person
$1,265
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $888, price is now $640 per person
$640
per person
Nov 26 - Dec 1
found 15 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,152, price is now $836 per person
$836
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

6-7 night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Price was $1,029, price is now $706 per person
$706
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,535, price is now $889 per person
$889
per person
Nov 18 - Nov 25
found 1 day ago
Roundtrip non-stop 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 $2,632, price is now $1,652 per person
$1,652
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $1,360, price is now $884 per person
$884
per person
Nov 6 - Nov 13
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,043, price is now $1,377 per person
$1,377
per person
Nov 7 - Nov 14
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,518, price is now $1,036 per person
$1,036
per person
Nov 21 - Nov 28
found 1 hour ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Resort Sixty-Six

Resort Sixty-Six

2.5 out of 5
Price was $1,768, price is now $1,258 per person
$1,258
per person
Nov 21 - Nov 28
found 1 hour ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $1,871, price is now $1,332 per person
$1,332
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Inn on the Beach - 18+ only

Inn on the Beach - 18+ only

2.5 out of 5
Price was $1,705, price is now $1,214 per person
$1,214
per person
Nov 8 - Nov 14
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
Price was $1,227, price is now $876 per person
$876
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Calini Beach Club by Coolvacay

Calini Beach Club by Coolvacay

3 out of 5
Price was $2,515, price is now $1,813 per person
$1,813
per person
Nov 21 - Nov 28
found 1 hour 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 $4,482, price is now $3,241 per person
$3,241
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

Fri, Nov 13 - Sun, Nov 15
SJU
San Juan
MCO
Orlando
$146 Roundtrip, found 6 hours ago
$146
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Nov 13 from San Juan to Orlando, returning Sun, Nov 15, priced at $146 found 6 hours ago
Fri, Nov 6 - Mon, Nov 9
SJU
San Juan
TPA
Tampa
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 6 from San Juan to Tampa, returning Mon, Nov 9, priced at $184 found 1 day ago
Mon, Dec 7 - Sun, Dec 13
SEA
Seattle
MCO
Orlando
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Mon, Dec 7 from Seattle to Orlando, returning Sun, Dec 13, priced at $315 found 2 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
$219 nightly
The price is $246 total per night
$246 total
Nov 4 - Nov 5
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
$177 nightly
The price is $201 total per night
$201 total
Nov 1 - Nov 2
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
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
31.98 mi from city center
$116 nightly
The price is $132 total per night
$132 total
Oct 14 - Oct 15
Total with taxes and fees
Located in Kissimmee, Hilton Vacation Club Mystic Dunes Orlando is within a 15-minute drive of Disney's Hollywood Studios® and Disney Springs™.
Pool
Free WiFi
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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.