Lakeland - Winter Haven Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Lakeland - Winter Haven vacation rentals

6 outdoor pools, free cabanas, pool umbrellas

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
Orlando
9.2 out of 10, Wonderful, (5,868 reviews)
"I can’t wait to come back again, Best place for family Vacation!!!"
United States
Ivelisse
The price is P10,331
P11,622 total
includes taxes & fees
Jul 14 - Jul 15
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,378 reviews)
"Great stay"
United States
Martena
The price is P3,923
P5,980 total
includes taxes & fees
Jun 28 - Jun 29
Vacation Village Orlando, Celebration
Property amenity

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, Wonderful, (571 reviews)
"Everything about this property is awesome! Clean, spacious, convenient, affordable!! We had a great stay!"
United States
Nina
The price is P7,586
P9,592 total
includes taxes & fees
Jun 25 - Jun 26
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Exterior

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (2,032 reviews)
"Excellent stay. Everything was perfect."
United States
Jorge
The price is P13,693
P27,777 total
includes taxes & fees
Jul 20 - Jul 21
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Terrace/patio

Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village
4.0 star property
Bay Lake
9.0 out of 10, Wonderful, (169 reviews)
"Yes all was excellent "
United States
Todd
Disney's Animal Kingdom Villas - Kidani Village
2 outdoor pools, pool umbrellas, sun loungers

Marriott's Royal Palms

Marriott's Royal Palms
4.0 star property
Orlando
9.4 out of 10, Exceptional, (302 reviews)
"Great staff, very friendly "
United States
Michael
The price is P11,187
P12,585 total
includes taxes & fees
Jul 14 - Jul 15
Marriott's Royal Palms
3 outdoor pools

Disney's Beach Club Villas

Disney's Beach Club Villas
5.0 star property
Bay Lake
9.2 out of 10, Wonderful, (39 reviews)
"Clean and great location"
United States
Anonymous traveler
Disney's Beach Club Villas
Lake

Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (210 reviews)
"Camp Mack is a wonderful place to stay!"
United States
Tommy
The price is P6,499
P7,279 total
includes taxes & fees
Jul 12 - Jul 13
Camp Mack Lodge, Marina & RV Resort
Exterior

WorldQuest Orlando Resort

WorldQuest Orlando Resort
4.0 star property
Orlando
8.4 out of 10, Very Good, (4,076 reviews)
"The hospitality was remarkable. The front desk attendants Odette and LaKetra were both so pleasant and helpful. My family and I really enjoyed our time on the property. Thank you again team for all you do."
United States
Mya
The price is P9,137
P17,844 total
includes taxes & fees
Jun 27 - Jun 28
WorldQuest Orlando Resort
Outdoor pool, pool umbrellas, sun loungers

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,881 reviews)
"Excellent stay!"
United States
Ed
The price is P4,903
P6,766 total
includes taxes & fees
Jul 12 - Jul 13
Barefoot Suites
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers

Marriott's Sabal Palms

Marriott's Sabal Palms
4.0 star property
Orlando
9.6 out of 10, Exceptional, (219 reviews)
"Wonderful stay for a family of five and close to Disney World and surrounding parks! Large spaces, comfortable beds and access to Kitchen and washer and dryer! Would gladly return for another Disney trip!"
United States
Melissa
The price is P10,637
P11,967 total
includes taxes & fees
Jul 16 - Jul 17
Marriott's Sabal Palms
Exterior

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (326 reviews)
"When my family come to the theme parks, THIS is always our place to stay."
United States
Justin
The price is P7,378
P9,133 total
includes taxes & fees
Jun 24 - Jun 25
Barefoot'n Resort Kissimmee Orlando
Interior

Upstay: Family-friendly Getaway With Spa & Pool

Upstay: Family-friendly Getaway With Spa & Pool
3.5 star property
Orlando
10.0 out of 10, Exceptional, (1 review)
"Clean room"
United States
Yves marie
The price is P5,288
P14,771 total
includes taxes & fees
Jun 24 - Jun 25
Upstay: Family-friendly Getaway With Spa & Pool
Lobby sitting area

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,273 reviews)
"I love the location of this place."
United States
William
The price is P9,170
P11,003 total
includes taxes & fees
Jun 25 - Jun 26
The Berkley, Orlando
Exterior

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very Good, (3,159 reviews)
"The price is reasonable and staff are really nice."
Canada
Moonyeen
The price is P5,353
P18,148 total
includes taxes & fees
Jun 24 - Jun 25
Regal Oaks Resort Vacation Townhomes by IDILIQ
Lobby

Marriott's Imperial Palm Villas

Marriott's Imperial Palm Villas
4.0 star property
Orlando
9.2 out of 10, Wonderful, (63 reviews)
"Brilliant place would highly recommend and close to Disney parks"
United Kingdom
Matthew
The price is P17,445
P19,626 total
includes taxes & fees
Jul 13 - Jul 14
Marriott's Imperial Palm Villas
Interior

Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is P10,030
P25,807 total
includes taxes & fees
Jun 24 - Jun 25
Golf, Dine & Unwind Poolside! Haines City Getaway
Outdoor pool

The Irlo

The Irlo
3.0 star property
Kissimmee
7.4 out of 10, Good, (31 reviews)
"Management and staff have been amazing gave me a tour the facility"
United States
Robert
The price is P2,629
P4,371 total
includes taxes & fees
Jun 25 - Jun 26
The Irlo
Exterior

Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14

Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14
4.5 star property
Lindfields
The price is P16,138
P31,770 total
includes taxes & fees
Jun 24 - Jun 25
Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14
Water park

Six BR Home at ChampionsGate Resort

Six BR Home at ChampionsGate Resort
5.0 star property
Champions Gate
The price is P21,988
P50,351 total
includes taxes & fees
Jun 25 - Jun 26
Six BR Home at ChampionsGate Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lakeland - Winter Haven Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8/10 Good
"this was my first stay at Holiday Inn at Orange Lake. I was pleasantly surprised. the Property is large, nonetheless, food and activities is within 10 min drive. additionally, if you do no want to leave the property you don't have to, they have activities on site. the villa had enough room for my family, along with a nice size kitchen, 2 bathrooms, living and dining room, and full size washer and dryers. the stay was friendly and pleasant. if you need place to stay, please do not skip over this resort."
Angela 3-night trip
Posted 1 hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Lakeland - Winter Haven

Search for holiday rentals in Lakeland - Winter Haven on Expedia! You can easily find your home rentals, villas, holiday apartments in Lakeland - Winter Haven using one of the methods below:

  • View our selection of featured holiday rentals in Lakeland - Winter Haven
  • Use the map to find apartments and other holiday homes in the Lakeland - Winter Haven neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Lakeland - Winter Haven while they last

Look no further and take a look at our great range of rental properties in Lakeland - Winter Haven!