Cheap Vacations in Lakeland - Winter Haven

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3-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Price was $523, price is now $372 per person
$372
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $739, price is now $465 per person
$465
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $705, price is now $487 per person
$487
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,059, price is now $758 per person
$758
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $729 per person
$729
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $635, price is now $456 per person
$456
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $939, price is now $685 per person
$685
per person
Jun 4 - Jun 7
found 1 day 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 $1,409, price is now $1,031 per person
$1,031
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Price was $723, price is now $535 per person
$535
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Siesta Key Palms Resort

Siesta Key Palms Resort

3.5 out of 5
Price was $872, price is now $645 per person
$645
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was $570, price is now $424 per person
$424
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Price was $855, price is now $638 per person
$638
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $747, price is now $525 per person
$525
per person
May 24 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $1,055, price is now $623 per person
$623
per person
May 23 - May 30
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,285, price is now $785 per person
$785
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Price was $1,274, price is now $783 per person
$783
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,519, price is now $1,580 per person
$1,580
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,370, price is now $867 per person
$867
per person
May 30 - Jun 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,922, price is now $1,272 per person
$1,272
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,126, price is now $747 per person
$747
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,194, price is now $793 per person
$793
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,302, price is now $877 per person
$877
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,677, price is now $1,144 per person
$1,144
per person
Jun 6 - Jun 12
found 8 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $1,350, price is now $947 per person
$947
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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, May 7 - Mon, May 11
SJU
San Juan
TPA
Tampa
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, May 7 from San Juan to Tampa, returning Mon, May 11, priced at $167 found 4 days ago
Fri, Apr 24 - Sat, Apr 25
SJU
San Juan
MCO
Orlando
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Fri, Apr 24 from San Juan to Orlando, returning Sat, Apr 25, priced at $171 found 5 days ago
Fri, May 29 - Fri, Jun 5
SEA
Seattle
TPA
Tampa
$226 Roundtrip, found 21 hours ago
$226
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Fri, May 29 from Seattle to Tampa, returning Fri, Jun 5, priced at $226 found 21 hours 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
$228 nightly
The price is $257 total per night
$257 total
May 11 - May 12
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.
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
33.51 mi from city center
$180 nightly
The price is $204 total per night
$204 total
May 20 - May 21
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
31.98 mi from city center
$130 nightly
The price is $148 total per night
$148 total
Apr 28 - Apr 29
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™.
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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.