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.
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3 out of 5
Terrace Park
Price was $564, price is now $423 per person
$423
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Price was $970, price is now $692 per person
$692
per person
Apr 20 - Apr 24
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Virginia Park
Price was $576, price is now $424 per person
$424
per person
Apr 10 - Apr 13
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
Sunshine Beach
Price was $1,307, price is now $968 per person
$968
per person
Apr 18 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was $1,515, price is now $1,142 per person
$1,142
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Price was $2,110, price is now $1,597 per person
$1,597
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $934, price is now $712 per person
$712
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $1,228, price is now $939 per person
$939
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
BeachTrail Lodging

BeachTrail Lodging

3 out of 5
Save 100% on your flight
Price was $1,603, price is now $1,227 per person
$1,227
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Arvilla

Arvilla

2 out of 5
Sunshine Beach
Price was $1,427, price is now $1,096 per person
$1,096
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

3-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
BAY INN

BAY INN

2 out of 5
Price was $404, price is now $318 per person
$318
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $616, price is now $409 per person
$409
per person
May 1 - May 4
just found
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $912, price is now $669 per person
$669
per person
Apr 23 - Apr 26
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Price was $576, price is now $424 per person
$424
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Arvilla

Arvilla

2 out of 5
Price was $713, price is now $530 per person
$530
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3 out of 5
Price was $564, price is now $423 per person
$423
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $1,110, price is now $845 per person
$845
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Price was $1,677, price is now $1,285 per person
$1,285
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip 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 $990, price is now $773 per person
$773
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Price was $841, price is now $665 per person
$665
per person
Apr 4 - Apr 7
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Price was $1,021, price is now $809 per person
$809
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $468, price is now $374 per person
$374
per person
Apr 14 - Apr 17
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

4-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
Price was $438, price is now $330 per person
$330
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Price was $970, price is now $692 per person
$692
per person
Apr 20 - Apr 24
found 4 hours 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
Price was $1,307, price is now $968 per person
$968
per person
Apr 18 - Apr 22
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 $588, price is now $438 per person
$438
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
BeachTrail Lodging

BeachTrail Lodging

3 out of 5
Save 100% on your flight
Price was $1,059, price is now $807 per person
$807
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $934, price is now $712 per person
$712
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $1,228, price is now $939 per person
$939
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Arvilla

Arvilla

2 out of 5
Price was $1,427, price is now $1,096 per person
$1,096
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $541, price is now $419 per person
$419
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Price was $1,269, price is now $984 per person
$984
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Save 100% on your flight
Price was $817, price is now $634 per person
$634
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Crystal Palms Beach Resort

Crystal Palms Beach Resort

4 out of 5
Save 100% on your flight
Price was $898, price is now $700 per person
$700
per person
Apr 27 - May 1
just found
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)

5-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
Price was $523, price is now $365 per person
$365
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $811, price is now $484 per person
$484
per person
Apr 14 - Apr 19
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,358, price is now $817 per person
$817
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $795, price is now $509 per person
$509
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $848, price is now $558 per person
$558
per person
Apr 11 - Apr 16
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
Save 100% on your flight
Price was $816, price is now $559 per person
$559
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $887, price is now $615 per person
$615
per person
Apr 11 - Apr 16
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
Price was $1,471, price is now $1,046 per person
$1,046
per person
Apr 17 - Apr 22
found 2 days 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 $1,445, price is now $1,035 per person
$1,035
per person
Apr 17 - Apr 22
found 2 days 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 $2,399, price is now $1,766 per person
$1,766
per person
Apr 17 - Apr 22
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Price was $1,328, price is now $994 per person
$994
per person
Apr 17 - Apr 22
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
THE RESERVE RETREAT

THE RESERVE RETREAT

2 out of 5
Save 100% on your flight
Price was $769, price is now $576 per person
$576
per person
Apr 11 - Apr 16
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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $953, price is now $452 per person
$452
per person
Apr 14 - Apr 21
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,733, price is now $1,066 per person
$1,066
per person
Apr 22 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Save 100% on your flight
Price was $1,049, price is now $680 per person
$680
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,406, price is now $961 per person
$961
per person
Apr 12 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,034, price is now $725 per person
$725
per person
Apr 12 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $2,943, price is now $2,076 per person
$2,076
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
Price was $2,114, price is now $1,510 per person
$1,510
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $2,320, price is now $1,663 per person
$1,663
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip non-stop 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 $1,531, price is now $1,110 per person
$1,110
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,113, price is now $1,542 per person
$1,542
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Landing Tampa Westshore

Landing Tampa Westshore

4.5 out of 5
Save 100% on your flight
Price was $1,182, price is now $877 per person
$877
per person
Apr 15 - Apr 22
found 14 hours 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 $3,424, price is now $2,547 per person
$2,547
per person
Apr 18 - Apr 25
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 14 - Mon, May 18
SJU
San Juan
TPA
Tampa
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 14 from San Juan to Tampa, returning Mon, May 18, priced at $138 found 1 day ago
Wed, Mar 11 - Wed, Mar 18
SJU
San Juan
MCO
Orlando
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Mar 11 from San Juan to Orlando, returning Wed, Mar 18, priced at $168 found 1 day ago
Fri, Apr 10 - Thu, Apr 16
SEA
Seattle
TPA
Tampa
$203 Roundtrip, found 5 days ago
$203
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Apr 10 from Seattle to Tampa, returning Thu, Apr 16, priced at $203 found 5 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
34.59 mi from city center
$208 nightly
The price is $234 total per night
$234 total
Mar 22 - Mar 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.
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
$276 nightly
The price is $311 total per night
$311 total
Mar 12 - Mar 13
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 ChampionsGate Golf Club.
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
$145 nightly
The price is $165 total per night
$165 total
Mar 22 - Mar 23
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™.
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.