Cheap Vacations in Lakeland - Winter Haven

Choose two or more items and save on your trip:

3-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection Hotel

The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection Hotel

2.5 out of 5
Price was $623, price is now $504 per person
$504
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,912, price is now $1,300 per person
$1,300
per person
Jun 25 - Jun 28
found 6 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,562, price is now $1,169 per person
$1,169
per person
Jun 25 - Jun 28
found 6 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $877, price is now $665 per person
$665
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $725, price is now $561 per person
$561
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was $1,214, price is now $950 per person
$950
per person
Jun 25 - Jun 28
found 6 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Tampa (TPA)
The Capri at Siesta

The Capri at Siesta

3 out of 5
Price was $850, price is now $672 per person
$672
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $879, price is now $703 per person
$703
per person
Jun 25 - Jun 28
found 6 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $740, price is now $594 per person
$594
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort

3 out of 5
Price was $1,172, price is now $950 per person
$950
per person
Jun 25 - Jun 28
found 6 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Tampa (TPA)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Price was $819, price is now $666 per person
$666
per person
Jun 25 - Jun 28
found 6 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Tampa (TPA)
Treasure Island Hotel and Marina

Treasure Island Hotel and Marina

3 out of 5
Price was $874, price is now $715 per person
$715
per person
Jun 25 - Jun 28
found 6 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Tampa (TPA)

4-night Lakeland - Winter Haven vacations

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

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,032, price is now $682 per person
$682
per person
Jun 3 - Jun 7
found 19 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Tampa (TPA)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
Price was $2,262, price is now $1,520 per person
$1,520
per person
Jun 8 - Jun 12
found 4 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,783, price is now $1,247 per person
$1,247
per person
Jun 8 - Jun 12
found 4 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,043, price is now $769 per person
$769
per person
Jun 8 - Jun 12
found 4 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Price was $907, price is now $688 per person
$688
per person
Jun 11 - Jun 15
found 18 hours ago
Roundtrip flight included
Chicago (MDW) to Tampa (TPA)
Anna Maria Island Sun s Up A

Anna Maria Island Sun s Up A

2.5 out of 5
Save 100% on your flight
Price was $17,703, price is now $13,611 per person
$13,611
per person
Jun 8 - Jun 12
found 4 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
Anna Maria Island Sun s Up B

Anna Maria Island Sun s Up B

3 out of 5
Save 100% on your flight
Price was $17,703, price is now $13,611 per person
$13,611
per person
Jun 8 - Jun 12
found 4 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
AMI Lighthouse Cottage-one Minute Walk To The Beach-keyless Locks

AMI Lighthouse Cottage-one Minute Walk To The Beach-keyless Locks

3.5 out of 5
Save 100% on your flight
Price was $13,127, price is now $10,100 per person
$10,100
per person
Jun 8 - Jun 12
found 4 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $911, price is now $706 per person
$706
per person
Jun 1 - Jun 5
found 13 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $950, price is now $739 per person
$739
per person
Jun 1 - Jun 5
found 9 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $1,395, price is now $1,086 per person
$1,086
per person
Jun 1 - Jun 5
found 13 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Price was $1,126, price is now $878 per person
$878
per person
Jun 8 - Jun 12
found 4 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)

5-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $612, price is now $460 per person
$460
per person
Jun 1 - Jun 6
found 19 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,073, price is now $1,526 per person
$1,526
per person
Jun 15 - Jun 20
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Tampa (TPA)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Price was $977, price is now $772 per person
$772
per person
Jun 15 - Jun 20
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Tampa (TPA)
Treasure Island Hotel and Marina

Treasure Island Hotel and Marina

3 out of 5
Price was $1,095, price is now $868 per person
$868
per person
Jun 15 - Jun 20
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Tampa (TPA)
St Pete Shores Hotel

St Pete Shores Hotel

3 out of 5
Price was $915, price is now $727 per person
$727
per person
Jun 15 - Jun 20
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,766, price is now $1,413 per person
$1,413
per person
Jun 15 - Jun 20
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,106, price is now $691 per person
$691
per person
Jun 1 - Jun 6
found 19 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,416, price is now $896 per person
$896
per person
Jun 1 - Jun 6
found 19 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $853, price is now $584 per person
$584
per person
Jun 1 - Jun 6
found 19 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Tampa (TPA)
Hilton St. Petersburg Carillon Park

Hilton St. Petersburg Carillon Park

4 out of 5
Save 100% on your flight
Price was $958, price is now $708 per person
$708
per person
Jun 23 - Jun 28
found 12 hours ago
Roundtrip flight included
Chicago (MDW) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $862, price is now $645 per person
$645
per person
Jun 1 - Jun 6
found 19 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $920, price is now $690 per person
$690
per person
Jun 1 - Jun 6
found 19 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Tampa (TPA)

6-7 night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Price was $1,056, price is now $798 per person
$798
per person
Jun 18 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,513, price is now $1,649 per person
$1,649
per person
Jun 14 - Jun 20
found 5 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,584, price is now $1,775 per person
$1,775
per person
Jun 14 - Jun 20
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $2,033, price is now $1,434 per person
$1,434
per person
Jun 14 - Jun 20
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $1,318, price is now $950 per person
$950
per person
Jun 14 - Jun 20
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,554, price is now $1,120 per person
$1,120
per person
Jun 14 - Jun 20
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Best Western Plus Yacht Harbor Inn

Best Western Plus Yacht Harbor Inn

2.5 out of 5
Save 100% on your flight
Price was $1,277, price is now $931 per person
$931
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Tampa (TPA)
Provident Oceana Beachfront Suites

Provident Oceana Beachfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,628, price is now $1,215 per person
$1,215
per person
Jun 14 - Jun 20
found 5 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Treasure Island Hotel and Marina

Treasure Island Hotel and Marina

3 out of 5
Price was $1,335, price is now $1,009 per person
$1,009
per person
Jun 14 - Jun 20
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $2,045, price is now $1,550 per person
$1,550
per person
Jun 14 - Jun 20
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Stones Throw Beachfront Luxury Suites

Stones Throw Beachfront Luxury Suites

2 out of 5
Price was $1,518, price is now $1,155 per person
$1,155
per person
Jun 14 - Jun 20
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Price was $1,147, price is now $873 per person
$873
per person
Jun 14 - Jun 20
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) 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, May 9 - Mon, May 11
SJU
San Juan
MCO
Orlando
$141 Roundtrip, found 6 days ago
$141
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 9 from San Juan to Orlando, returning Mon, May 11, priced at $141 found 6 days ago
Sat, May 9 - Sat, May 16
SJU
San Juan
TPA
Tampa
$194 Roundtrip, found 6 days ago
$194
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 9 from San Juan to Tampa, returning Sat, May 16, priced at $194 found 6 days ago
Thu, May 28 - Sun, May 31
SEA
Seattle
TPA
Tampa
$226 Roundtrip, found 2 days ago
$226
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 28 from Seattle to Tampa, returning Sun, May 31, priced at $226 found 2 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
34.59 mi from city center
$214 nightly
The price is $241 total per night
$241 total
May 14 - May 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 with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
33.51 mi from city center
$192 nightly
The price is $217 total per night
$217 total
May 11 - May 12
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
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
7700 Westgate Blvd. Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
32.79 mi from city center
$120 nightly
The price is $137 total per night
$137 total
May 3 - May 4
Total with taxes and fees
When you stay at Westgate Town Center Resort in Kissimmee, you'll be on a lake, a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Lakeland - Winter Haven
View all properties
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.