Cheap Vacations in Lakeland - Winter Haven

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Lakeland - Winter Haven vacations

Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
May 26 - Jun 1
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
per person
May 26 - Jun 1
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip non-stop 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
Belle Vista
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
May 26 - Jun 1
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 1
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 1
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 1
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Prices and availability subject to change. Additional terms may apply.

3-night Lakeland - Winter Haven vacations

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop 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
per person
May 24 - May 27
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
May 24 - May 27
Roundtrip 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
per person
May 31 - Jun 3
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Haya

Hotel Haya

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) 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
Jun 14 - Jun 17
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 2
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
per person
May 24 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 16
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Saint Hotel

The Saint Hotel

3.5 out of 5
Save 100% on your flight
per person
May 31 - Jun 3
Roundtrip flight included
Raleigh (RDU) to Tampa (TPA)
Prices and availability subject to change. Additional terms may apply.

4-night Lakeland - Winter Haven vacations

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop 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
per person
May 23 - May 27
Roundtrip non-stop 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
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
May 23 - May 27
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
per person
Jun 10 - Jun 14
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) 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
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Postcard Inn On The Beach

Postcard Inn On The Beach

3 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Prices and availability subject to change. Additional terms may apply.

5-night Lakeland - Winter Haven vacations

Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Chicago (ORD) 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
Jun 6 - Jun 11
Roundtrip non-stop flight included
Chicago (ORD) 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
Jun 9 - Jun 14
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
May 29 - Jun 3
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Save 100% on your flight
per person
May 29 - Jun 3
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Chicago (ORD) 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
May 29 - Jun 3
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Clearwater Beach Hotel

Clearwater Beach Hotel

2 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 14
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 11
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Prices and availability subject to change. Additional terms may apply.

6-7 night Lakeland - Winter Haven vacations

Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 22
Roundtrip flight included
Raleigh (RDU) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
per person
May 24 - May 31
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
May 26 - Jun 1
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
per person
May 26 - Jun 1
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
per person
May 26 - Jun 1
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
May 29 - Jun 4
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Save 100% on your flight
per person
May 29 - Jun 4
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
per person
May 29 - Jun 4
Roundtrip non-stop flight included
Boston (BOS) 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
Jun 10 - Jun 16
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Treasure Bay Resort & Marina

Treasure Bay Resort & Marina

3 out of 5
Save 100% on your flight
per person
May 26 - Jun 1
Roundtrip flight included
Boston (BOS) 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
May 29 - Jun 4
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
May 26 - Jun 1
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Prices and availability subject to change. Additional terms may apply.

Flight deals to Lakeland - Winter Haven

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, May 14 - Tue, May 14
SJU
San Juan
MCO
Orlando
$79 Roundtrip, found 14 hours ago
$79
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Tue, May 14 from San Juan to Orlando, returning Tue, May 14, priced at $79 found 14 hours ago
Wed, May 1 - Sat, May 4
SJU
San Juan
TPA
Tampa
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, May 1 from San Juan to Tampa, returning Sat, May 4, priced at $88 found 3 days ago
Wed, May 15 - Fri, May 17
SEA
Seattle
TPA
Tampa
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 15 from Seattle to Tampa, returning Fri, May 17, priced at $140 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
The price is $197 per night
$197
per night
May 13 - May 14
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
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
Apr 29 - Apr 30
Located in Kissimmee, Hilton Vacation Club Mystic Dunes Orlando is within a 15-minute drive of Disney's Hollywood Studios® and Disney Springs™.
Pool
Breakfast available
Liki Tiki Village

Liki Tiki Village

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 $76 per night
$76
per night
Apr 29 - Apr 30
Located in Four Corners, 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.