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.
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
Westshore
Save 100% on your flight
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Belle Vista
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Save 100% on your flight
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Postcard Inn On The Beach

Postcard Inn On The Beach

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Clearwater Beach Marriott Suites on Sand Key

Clearwater Beach Marriott Suites on Sand Key

4 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)

4-night Lakeland - Winter Haven vacations

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

Innisbrook Resort

3.5 out of 5
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
Courtyard by Marriott Clearwater Beach

Courtyard by Marriott Clearwater Beach

3 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
Postcard Inn On The Beach

Postcard Inn On The Beach

3 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
AC Hotel Clearwater Beach

AC Hotel Clearwater Beach

3 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
Beachcomber Beach Resort

Beachcomber Beach Resort

2.5 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)

5-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 4
found 1 day 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
per person
Jul 21 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Courtyard by Marriott Clearwater Beach

Courtyard by Marriott Clearwater Beach

3 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Clearwater Beach Hotel

Clearwater Beach Hotel

2 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Clearwater Beach Marriott Suites on Sand Key

Clearwater Beach Marriott Suites on Sand Key

4 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
AC Hotel Clearwater Beach

AC Hotel Clearwater Beach

3 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
The Godfrey Hotel & Cabanas Tampa

The Godfrey Hotel & Cabanas Tampa

3.5 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 4
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.
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
Save 100% on your flight
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Postcard Inn On The Beach

Postcard Inn On The Beach

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.

Sat, Aug 24 - Wed, Sep 4
SJU
San Juan
TPA
Tampa
$84 Roundtrip, found 3 days ago
$84
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Aug 24 from San Juan to Tampa, returning Wed, Sep 4, priced at $84 found 3 days ago
Mon, Jun 24 - Wed, Jun 26
SJU
San Juan
MCO
Orlando
$113 Roundtrip, found 2 days ago
$113
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Jun 24 from San Juan to Orlando, returning Wed, Jun 26, priced at $113 found 2 days ago
Mon, Aug 5 - Tue, Aug 13
SEA
Seattle
MCO
Orlando
$179 Roundtrip, found 16 hours ago
$179
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Mon, Aug 5 from Seattle to Orlando, returning Tue, Aug 13, priced at $179 found 16 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
34.52 mi from city center
The price is $221 per night
$221
per night
Jun 26 - Jun 27
Located in Winter Garden, 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
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

3.5 out of 5
7600 Mystic Dunes Lane, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
31.98 mi from city center
The price is $87 per night
$87
per night
Jul 10 - Jul 11
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
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

3.5 out of 5
17777 Bali Blvd, Winter Garden, FL
Free Cancellation
Reserve now, pay when you stay
33.83 mi from city center
The price is $79 per night
$79
per night
Jun 26 - Jun 27
Located in Winter Garden, Hilton Vacation Club Aqua Sol Orlando West is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club.
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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.