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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $499, price is now $397 per person
$397
per person
Jun 9 - Jun 12
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,557, price is now $1,110 per person
$1,110
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $638, price is now $488 per person
$488
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $1,952, price is now $1,506 per person
$1,506
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Price was $696, price is now $537 per person
$537
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Longboat Bay Club by Coolvacay

Longboat Bay Club by Coolvacay

3.5 out of 5
Price was $782, price is now $609 per person
$609
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was $1,164, price is now $908 per person
$908
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $9,621, price is now $7,560 per person
$7,560
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Anna Maria Beach Serenity

Anna Maria Beach Serenity

2.5 out of 5
Save 100% on your flight
Price was $20,919, price is now $16,660 per person
$16,660
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Inn on the Beach

Inn on the Beach

2.5 out of 5
Price was $719, price is now $578 per person
$578
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $1,988, price is now $1,605 per person
$1,605
per person
Jun 25 - Jun 28
found 8 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Tampa (TPA)
Turtle Beach Resort

Turtle Beach Resort

3.5 out of 5
Price was $951, price is now $770 per person
$770
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

4-night Lakeland - Winter Haven vacations

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Sarasota/Bradenton-Airport, FL

Hampton Inn & Suites Sarasota/Bradenton-Airport, FL

2.5 out of 5
Price was $755, price is now $550 per person
$550
per person
Jun 9 - Jun 13
found 11 hours ago
Roundtrip flight included
Chicago (ORD) 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 $2,851, price is now $1,798 per person
$1,798
per person
Jun 18 - Jun 22
found 9 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,786, price is now $1,157 per person
$1,157
per person
Jun 18 - Jun 22
found 9 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $1,073, price is now $745 per person
$745
per person
Jun 18 - Jun 22
found 9 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Tampa (TPA)
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Price was $812, price is now $574 per person
$574
per person
Jun 18 - Jun 22
found 9 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,665, price is now $1,185 per person
$1,185
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $858, price is now $623 per person
$623
per person
Jun 18 - Jun 22
found 9 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Tampa (TPA)
The Capri at Siesta

The Capri at Siesta

3 out of 5
Save 100% on your flight
Price was $964, price is now $700 per person
$700
per person
Jun 9 - Jun 13
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Turtle Beach Resort

Turtle Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,737, price is now $1,268 per person
$1,268
per person
Jun 18 - Jun 22
found 9 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $946, price is now $691 per person
$691
per person
Jun 9 - Jun 13
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was $958, price is now $705 per person
$705
per person
Jun 18 - Jun 22
found 9 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $1,000, price is now $749 per person
$749
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Tampa (TPA)

5-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 $785, price is now $556 per person
$556
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,995, price is now $1,189 per person
$1,189
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $3,047, price is now $2,042 per person
$2,042
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $952, price is now $665 per person
$665
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,255, price is now $886 per person
$886
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,636, price is now $1,159 per person
$1,159
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip 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
Price was $1,270, price is now $902 per person
$902
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $1,250, price is now $902 per person
$902
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,886, price is now $1,372 per person
$1,372
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Save 100% on your flight
Price was $6,269, price is now $4,581 per person
$4,581
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $931, price is now $683 per person
$683
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,043, price is now $769 per person
$769
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

6-7 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
Price was $928, price is now $695 per person
$695
per person
Jun 26 - Jul 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,853, price is now $1,203 per person
$1,203
per person
Jun 26 - Jul 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 22 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 22 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,157, price is now $807 per person
$807
per person
Jun 26 - Jul 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 22 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 22 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 22 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort

3 out of 5
Save 100% on your flight
Price was $1,653, price is now $1,197 per person
$1,197
per person
Jun 26 - Jul 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 22 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
Price was $1,232, price is now $929 per person
$929
per person
Jun 14 - Jun 20
just found
Roundtrip flight included
Los Angeles (LAX) to Tampa (TPA)
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)

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 - Sat, May 16
SJU
San Juan
MCO
Orlando
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 9 from San Juan to Orlando, returning Sat, May 16, priced at $142 found 1 day ago
Tue, Aug 4 - Mon, Aug 24
SJU
San Juan
TPA
Tampa
$197 Roundtrip, found 6 hours ago
$197
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Aug 4 from San Juan to Tampa, returning Mon, Aug 24, priced at $197 found 6 hours 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
$183 nightly
The price is $208 total per night
$208 total
May 17 - May 18
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
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
$188 nightly
The price is $212 total per night
$212 total
May 4 - May 5
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 Disney's Animal Kingdom® Theme Park.
Pool
Hot Tub
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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.