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.
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $396, price is now $260 per person
$260
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $881, price is now $514 per person
$514
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,408, price is now $827 per person
$827
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,326, price is now $805 per person
$805
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Crystal Palms Beach Resort

Crystal Palms Beach Resort

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,375, price is now $899 per person
$899
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $785, price is now $526 per person
$526
per person
Jan 29 - Feb 2
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $827, price is now $559 per person
$559
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Grant Street Inn, an Ascend Collection Hotel

Grant Street Inn, an Ascend Collection Hotel

2.5 out of 5
Downtown Dunedin
Save 100% on your flight
Price was $537, price is now $363 per person
$363
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $888, price is now $603 per person
$603
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)

3-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $396, price is now $260 per person
$260
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $608, price is now $284 per person
$284
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $873, price is now $513 per person
$513
per person
Jan 17 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $684, price is now $430 per person
$430
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $522, price is now $351 per person
$351
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $827, price is now $559 per person
$559
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $581, price is now $393 per person
$393
per person
Jan 17 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Grant Street Inn, an Ascend Collection Hotel

Grant Street Inn, an Ascend Collection Hotel

2.5 out of 5
Save 100% on your flight
Price was $537, price is now $363 per person
$363
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $542, price is now $369 per person
$369
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $403, price is now $276 per person
$276
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $763, price is now $525 per person
$525
per person
Jan 23 - Jan 26
found 9 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Price was $635, price is now $439 per person
$439
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

4-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Palm Cove Motel

Palm Cove Motel

2 out of 5
Price was $648, price is now $456 per person
$456
per person
Jan 15 - Jan 19
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $937, price is now $595 per person
$595
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,137, price is now $722 per person
$722
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $787, price is now $522 per person
$522
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,973, price is now $1,317 per person
$1,317
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $785, price is now $526 per person
$526
per person
Jan 29 - Feb 2
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $749, price is now $518 per person
$518
per person
Jan 29 - Feb 2
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Grant Street Inn, an Ascend Collection Hotel

Grant Street Inn, an Ascend Collection Hotel

2.5 out of 5
Save 100% on your flight
Price was $665, price is now $465 per person
$465
per person
Jan 11 - Jan 15
found 22 hours ago
Roundtrip flight included
Houston (IAH) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $735, price is now $521 per person
$521
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $734, price is now $520 per person
$520
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $826, price is now $586 per person
$586
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $912, price is now $656 per person
$656
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)

5-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $735, price is now $505 per person
$505
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,060, price is now $592 per person
$592
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $881, price is now $514 per person
$514
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,408, price is now $827 per person
$827
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Save 100% on your flight
Price was $927, price is now $609 per person
$609
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $1,104, price is now $730 per person
$730
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $888, price is now $603 per person
$603
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $868, price is now $591 per person
$591
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Grant Street Inn, an Ascend Collection Hotel

Grant Street Inn, an Ascend Collection Hotel

2.5 out of 5
Save 100% on your flight
Price was $979, price is now $670 per person
$670
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,399, price is now $960 per person
$960
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

4 out of 5
Save 100% on your flight
Price was $1,001, price is now $688 per person
$688
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)

6-7 night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $1,216, price is now $426 per person
$426
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,271, price is now $725 per person
$725
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,600, price is now $959 per person
$959
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $1,056, price is now $640 per person
$640
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,326, price is now $805 per person
$805
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,466, price is now $892 per person
$892
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Save 100% on your flight
Price was $1,110, price is now $698 per person
$698
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $1,182, price is now $763 per person
$763
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Grant Street Inn, an Ascend Collection Hotel

Grant Street Inn, an Ascend Collection Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,070, price is now $696 per person
$696
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,105, price is now $721 per person
$721
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Crystal Palms Beach Resort

Crystal Palms Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,375, price is now $899 per person
$899
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,870, price is now $1,240 per person
$1,240
per person
Jan 14 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.

Thu, Feb 5 - Mon, Feb 9
SJU
San Juan
TPA
Tampa
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Feb 5 from San Juan to Tampa, returning Mon, Feb 9, priced at $126 found 1 day ago
Wed, Feb 18 - Wed, Feb 25
SJU
San Juan
MCO
Orlando
$163 Roundtrip, found 5 days ago
$163
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Feb 18 from San Juan to Orlando, returning Wed, Feb 25, priced at $163 found 5 days ago
Tue, Feb 17 - Wed, Feb 25
SEA
Seattle
MCO
Orlando
$164 Roundtrip, found 6 days ago
$164
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Feb 17 from Seattle to Orlando, returning Wed, Feb 25, priced at $164 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
34.52 mi from city center
$198 nightly
The price is $223 total per night
$223 total
Dec 14 - Dec 15
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

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
$168 nightly
The price is $191 total per night
$191 total
Dec 15 - Dec 16
Total with taxes and fees
Located in Kissimmee, Margaritaville Resort Orlando is a 3-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
$128 nightly
The price is $145 total per night
$145 total
Dec 17 - Dec 18
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
Parking included
Don't see what you're looking for?
See all available properties in Lakeland - Winter Haven
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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.