Vacation Rentals By Owner In Winter Haven, FL

This fabulous 1-bedroom apartment in Winter Haven is perfect for your escape. The bedroom features a cozy queen bed, and the living room offers an enchanting sofa bed for additional guests. You'll find all the essentials like a hair dryer, iron, AC, and heating to make your stay comfortable. Relax in the serene atmosphere of this charming rental. We'll be available to answer any questions while you stay at our place.

Charming and Cozy Winter Haven Oasis

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$247.67

Fully furnished single story home on Lake Shipp; has boat dock, inground heated swimming pool. Two bedrooms (king & queen), two baths plus a queen murphy bed in living room. Three seasons room walks out to pool/lanai area then out to private beach and dock. Waterski/barefoot/wakeboard, fish, kayak or SUP from your back door - nearby slalom courses for water skiers. Home includes towels, bedding, kitchenware, laundry & even beach towels. Also two bikes available for your use. brbrLegoLand is minutes away, Disneyworld 33 miles. Great boating & skiing. YouTube TV and internet. brbrCall Jeff if you're interested in renting during a blocked period (Oct to May). No pets, animal free zone due to severe allergies. Outdoor security cameras mounted at the front door, in the carport and in the screened in room specifically to see exterior doors and the pool.

Lake Shipp House with pool and dock on the water

Winter Haven, Florida, United States

Bed

Bath

6

Sleeps

$726.19

Recharge your spirit at our extraordinary waterfront home on the famous Winter Haven Chain of (19) Lakes! brbrImmerse yourself in nature with spectacular lake views and vibrant sunsets. Perfect for families or couples looking to unwind.brbrEnjoy connected living from our thoughtful kitchen to the great room with expansive lake views to the enclosed patio for outside dining and entertaining,brbrWe are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary.brbrYOUR PROPERTYbrbrThis remarkable 4 bedroom 3-bath is more than 2700 sq. ft. and has everything you need for waterfront fun and relaxation. Step through the vaulted entry to escape into another world of natural beauty and comfort.brbrHIGHLIGHTS br+Custom built in 2012br+Waterfront on 3 sides of the property br+Covered dock with boat slipbr+West facing for fabulous sunsetsbr+Open design with elegant appointments by Gigibr+Lake view kitchen with oversized island and bar seating for 8br+Dedicated coffee barbr+Sweeping lake vistas connecting the kitchen, great room, pool and patio br+Screen enclosed pool patio & spa, griddle, bar and outdoor dining br+TVs in 3 roomsbr+Visit our host profile for our additional listings, including booking the house next doorbr+“Cypress Gardens Lake House” for more infobrbrWELCOMEbrbrAs owners this property, with an eye to retiring here in the next 5 years or so, we spend around 50 days a year on site, making upgrades and constant improvements. Because we actually spend quality personal time living in these houses, they have all the niceties and amenities you would expect from a family home. It’s personal to us, and we continually strive to make these spaces amazing for our ourselves and our guests.brbrINTERIORbr brSpanning over 2,700 square feet on one floor, the interior has a warm connecting feel opening to breathtaking lake vistas. brbrThe Great Room, kitchen and dining areas are independent yet connected to the screen enclosed pool bar and patio with the expanse of the open lake and private docks just a few steps beyond.brbrOur family, friends and guests universally comment on the great feeling of the connected common living spaces and how beautiful the sweeping lake views are from inside the house.brbrThe Great Room with extra high ceilings features relaxed seating for everyone to enjoy being together. brbrThe kitchen is well appointed for easy entertaining with bar seating and an oversized island. It includes a coffee bar with Keurig, Nespresso (Virtuo pods), French press, drip, coffee grinder, and electric kettle.brbrThe laundry room features raised front loading GE washer and dryer with a separate sink.brbrAttention to lighting is important to us and you will find numerous dimmers, up lights, and coffered ceilings with recessed lights to create the perfect ambiance.brWe have installed a robust business grade Internet system that covers the entire house and grounds. We have Spectrum Internet Gig (the fastest available). Our business IT provider monitors 24-7 for fast response. brbrWe have installed a whole house water softener for improved water quality. brbrFor drinking water aficionados, we have a installed a triple filter reverse osmosis water purification system at the kitchen sink for the best health and taste possible.brbr4 Roomsbrbr1. Private Master SuitebrTurn right at the welcome alcove through double French doors to enter an oasis of refined relaxation. The Tommy Bahamas half poster King Bed is beautiful an oh so comfy. Stream your favorites with our Samsung Smart TV. The sliding glass door on the right opens to the screened pool and lake beyond. Perfectly positioned on your left is the walk-in closet, walk in shower, master bath with soaking tub, and 2 separate sinks with vanities.brbr2. Pool RoombrRest easy in our Tommy Bahamas queen bed and en-suite bathroom with shower. The sliding glass door opens directly to the screened pool and lake beyond.brbr3. Queen RoombrQueen bed with large walk-in closet and Samsung Smart TV. En-suite bathroom & shower (with additional Great room access).brbr4. Twin RoombrTwo twin beds for single sleepers or kids. The whole room sits inside our signature “Fish Bowl” stylings. The space features a dedicated closet and Samsung Smart TV. A sturdy desk with basic office supplies can be used as a workspace area.brbr“Pull-Out Sofa”: add up to 2 more guests with our pull-out sofa in the great room. Bathroom access in the hall way is just off the great roombrbrAll bedrooms have dedicated closets and luggage racks.brbrEXTERIORbrbrThe property is a hidden gem waiting to be discovered. There’s plenty of room for playing and relaxing.brbrGet set for outdoor living with our screened lakeside area. A large portion including the dining set and bar area are protected and covered with the extension of the roof. The pool and spas beyond are perfectly positioned between the action of the house and the serenity of historic Lake Eloise. Our behind the bar Blackstone Griddle has dedicated venting to cook up your favorites. A beverage refrigerator behind the bar is perfect for keeping your food and drinks chilled and ready for sharing. brbrRelax in sun or shade with our two reclining lounge chairs: or take a load off with our love seat under shade and overlooking all the action.brbrThe pool is warmed by a Solar Heating System. Average Central Florida Pool Temperatures with this system are above 80 degrees from late February to late November. We have set the system to a max temperature of 86 degrees. The spa can be heated any time of year to 102 degrees with a gas heater at the push of a button.brbrBring or rent a boat for cruising the Chain of Lakes. It’s a perfect place for a water ski or wakeboard session on the world’s most famous watersports lake. If angling is your style, cast and reel on 18 connected lakes for a great fish story. We have a dedicated pontoon boat on site for rental. This is for guests only and is available for at a significantly discounted rate.brbrbrOur two docks are available for your pleasure. The main dock features covered boat slip with bumpers and additional space for lakeside relaxation. Our second dock in the southside canal affords views to the wilds of Cypress Gardens. brbrTake satisfaction knowing you're living your best life at our waterfront oasis. This is a place you won’t want to leave!

Expansive Lakeside Living at this Sunset Haven Gem

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$201.95

Million dollar lake view.brEagles nest in the back yard every year.brNo pets. No smoking. No children. No parties.brFurnished. brOne of a kind house.brLakefront. Lake Marianna is over 9 miles around the lake. brBeautiful Tennessee sandstone construction including exterior walls, patio, picnic table, grill, walkway and driveway. Rock walls are laid like brick.brInterior walls and ceiling are plaster. The bedrooms and living room are carpeted and the living room, dining room, laundry room and entry are Tennessee Sandstone floors.brCompletely furnished. Just bring your toothbrush and a change of clothes.brSome of the furnishings are antiques. brVery well built. Original owner was also a builder. Tennessee sandstone exterior walls and interior floor.brQuiet friendly established neighborhood with little turnover. Quiet restful house. brDisneyworld 30 miles. Legoland 11 miles.

Lakefront house for rent

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$99.78

Welcome to our studio apartment, a perfect retreat for solo travelers or couples seeking a comfortable and convenient place to stay. Nestled in a quiet neighborhood in Winter Haven, our studio offers a kitchen, living area with a TV equipped with streaming services for your entertainment, queen-size bed, and a full bathroom. We're committed to providing a cozy and comfortable home away from home for your visit. We look forward to hosting you in our lovely apartment!brbrThis studio apartment is located in a small complex of (5) total units and though the studio is private, the grounds are shared with others.brbrUpon entering, you'll find an inviting open-concept layout. The apartment is designed to maximize both space and functionality. The well-lit living room area is furnished with a sofa, perfect for unwinding after a day of exploring. You can catch up on your favorite shows or movies on the flat-screen TV, which is equipped with streaming services for your entertainment.brbrThe kitchen is equipped with all of the basics you would need to prepare meals. You will find a stove, oven, toaster, refrigerator, and basic cookware and utensils. The dining area is right next to the kitchen, providing a cozy spot for enjoying your meals.brbrThe unit includes a queen-size bed in a comfortable sleeping space to ensure a peaceful night's rest. You'll find ample storage for your belongings, making it easy to keep the area neat and organized during your stay.brbrThe full bathroom features a shower, toilet, and we provide towels and essential toiletries to ensure your stay is as convenient as possible.brbrThere is a laundry room available at the complex that is shared among the community. You will need coins and detergent to operate during your stay. brbrWe look forward to hosting you in beautiful Winter Haven, Florida!brbrThis studio apartment is on-site with (4) other units. The GPS will take you to the property, but it will not take you to the exact location you need to park. Your parking spot will be available at the back of the complex so you will need to drive around the yellow/green building to get to the blue building where you will be staying. brbrWinter Haven, Florida, offers a variety of activities and attractions in and around our Airbnb! Here are some things to do:brbr1. **LEGOLAND Florida Resort:** Just a short drive away, LEGOLAND offers a fantastic theme park experience with rides, shows, and intricate LEGO displays for families and LEGO enthusiasts.brbr2. **Chain of Lakes:** Enjoy boating, fishing, and water sports on the Chain of Lakes, including Lake Howard and Lake Cannon, which are nearby.brbr3. **Bok Tower Gardens:** Explore the picturesque gardens and experience the beautiful carillon tower, which hosts daily concerts.brbr4. **Lake Howard Park:** A great place for picnics, walking, or simply enjoying the lake views. There's also a playground for kids.brbr5. **Historic Downtown Winter Haven:** Stroll through the charming streets, visit local shops, dine in restaurants, and experience the town's historic architecture.brbr6. **Theatre Winter Haven:** If you're interested in the arts, check out local performances at this community theater.brbr7. **Golf:** Tee off at one of the nearby golf courses, such as Cypresswood Golf & Country Club.brbr8. **Shopping:** Explore nearby shopping centers like the Winter Haven Square and Cypress Gardens Boulevard for shopping and dining options.brbr9. **Cultural Attractions:** Visit local museums, like the Polk County Historical Museum, to learn about the area's history and culture.brbr10. **Outdoor Activities:** Enjoy hiking, biking, and wildlife watching in the various parks and preserves in the area.brbrRemember to check local event listings and seasonal activities for even more options to explore the Winter Haven area.

Studio Apartment in Winter Haven, FL

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$314.72

Your Winter Haven adventure begins at this 3-bedroom house. Inside, guests find a perfect blend of comfort with a king bed, queen bed, and a fun bunk bed. Two bathrooms offer convenience, each featuring a refreshing shower and a hair dryer. The house stays comfortable year-round with air conditioning and heating. Whether relaxing after a day of exploring or gathering for a meal, this wonderful home provides an excellent space to unwind. Experience the magic of Winter Haven at our house.

John Shirley's Retreat

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$426.33

Located just steps away from the pristine waters of the Chain of Lakes, this stunning 4-bedroom, 3.5-bathroom vacation rental is a water skier's paradise! Boasting calm, flat water conditions and on-site access to a private boat dock, this idyllic retreat invites you to watch the herons on quiet mornings before enjoying water sport adventures in the afternoons. Plus, this Winter Haven home offers easy access to top attractions, like LEGOLAND and Universal Studios, just a short drive away.brbr-- THE PROPERTY --brbr3,300 Sq Ft | Water Skiing Capital of the World | Private Boat Dock | Pet Friendly w/ Fee brbrBedroom 1: King Bed, Twin Bed | Bedroom 2: Queen Bed, Twin Bed | Bedroom 3: Queen Bed, Full Bed | Bedroom 4: 2 Twin/Full Bunk Beds w/ 2 Twin Trundles | Living Room: Sleeper Sofa | Game Room: Sleeper Sofa | Additional Sleeping: Pack ‘n Play brbrINDOOR LIVING: Smart TVs in all rooms, portable Bluetooth speaker, game room w/ pool table, board games, TV & bar, group-friendly dining table, fireplace brOUTDOOR LIVING: On-site Lake Mirror access, large unfenced backyard, kayaks, paddle boards, life jackets, gas grill, patio w/ 6-person seating, fire pit w/ seating, lounge area, 2 adult bikes, 2 child bikes, yard games, fishing poles, private hot tub, outdoor showerbrKITCHEN: Cooking basics, coffee maker, dishwasher, chef-grade cookware, stove/oven, refrigerator, microwave, instant hot water dispenser, water filtration system, updated kitchen appliances, high chair, spices, toaster, dishware & flatware, kitchen table brGENERAL: Free WiFi, complimentary toiletries, linens & towels, in-unit washer & dryer, central heating & air conditioning, laundry detergent, hair dryer, iron/board, trash bags & paper towels brFAQ: 4 exterior security cameras (facing out), pet fee (paid pre-stay), quiet hours (10:00 PM-7:00 AM) brACCESSIBILITY: 1 step required for entry, 2-story home brPARKING: Driveway (2 vehicles), garage (4 vehicles), free street parking, RV/trailer parking available on-sitebrbr-- THE LOCATION --brbrFAMILY FRIENDLY: Chain of Lakes Downtown Trailhead Park (1 mile), LEGOLAND Florida Water Park (6 miles), Reunion Resort Water Park (23 miles), Island H2O Water Park (29 miles), Aquatica Orlando (37 miles)brTEE TIME: Willowbrook Golf Course (4 miles), Lake Ashton Golf Club (11 miles), Bartow Golf Course (13 miles), Cleveland Heights Golf Course (15 miles), The Club at Eaglebrooke (19 miles)brTHRILLS GALORE: LEGO Ninjago World (6 miles), LEGOLAND® Florida Resort (6 miles), Universal Studios Florida (39 miles), Walt Disney World® Resort (46 miles) brAIRPORTS: Lakeland Linder International Airport (19 miles), Orlando International Airport (47 miles), Tampa International Airport (57 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly with a $75 fee (+ fees & taxes) br- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Your safety matters. This property features 4 exterior security cameras. These cameras are outward facing and do not look into any interior spaces. Camera 1 is located on the front door facing the front entrance, camera 2 is located on the front of the home facing the front entrance, camera 3 is located on the back of the home facing the patio, and camera 4 is located on the back of the home facing the dock. These cameras actively record video and audio when motion is detected and will be turned on during your stay br- NOTE: This 2-story home requires 1 step to enter and additional stairs to access some bedrooms and bathrooms on the upper floor br- NOTE: Please observe quiet hours from 10:00 PM-7:00 AM

Lakefront Winter Haven Retreat: Hot Tub & Patio!

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$208.88

Modern 2BR/2BA Apartment – Perfect for LEGOLAND GetawaysbrbrWelcome to your brand-new 2024 luxury apartment, conveniently located on the first floor near the entrance of this gated community. Designed for both comfort and convenience, this 2-bedroom, 2-bathroom unit offers a stylish and family-friendly retreat, just minutes from LEGOLAND.brbrCommunity Amenities:br • Heated resort-style poolbr • Full fitness center & conference roombr • Internet café & coworking spacesbr • Dog park & children’s playgroundbr • Outdoor grills, fire pits & picnic areasbrbrApartment Features:br • Spacious master bedroom with a king-size bedbr • Bunk bed with a pullout trundle in the kids’ roombr • Brand-new Smart TVs in every roombr • LEGO sets, board games & puzzles for family funbr • Fully equipped kitchen with all essential appliancesbr • In-unit washer & dryer for conveniencebrbrWhether you’re visiting LEGOLAND or simply seeking a relaxing escape, this thoughtfully designed apartment offers everything you need for an unforgettable stay.brbrPlease note that this unit is part of an apartment complex, and all VRBO units are located on the first floor for guest convenience and accessibility.brbrBecause of this, there are long-term residents living above you, often with children. Noise levels can vary — kids may be at school during the day, home on weekends, or sometimes home full-time. You may also hear barking dogs or general apartment noise from time to time.brbrWe’ve provided a white noise machine and earplugs in the unit for your comfort.brbrIf the noise becomes excessive and you can identify which apartment it’s coming from (for example, directly above you), please let the office know. Or I’ll contact the main office to report it on your behalf.brbrYou may also reach out to the apartment office directly during normal business hours (7 days a week).brbrIf the disturbance occurs at night, please visit or call the office the next day — they will follow up with the tenants and address the issue.brbrJust a quick reminder: we are guests of this apartment community, and all other residents are long-term tenants. Our unit is one of only two short-term rentals in the entire complex, so your courtesy and understanding are greatly appreciated.br

2-bedroom, 2-bath unit offers a family-friendly retreat just mins from LEGOLAND.

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$321.81

Welcome to your Lake Hamilton sunrise oasis!brbrThis waterfront home is designed for relaxed weekend escapes, where mornings begin with coffee by the water as the sun rises over the lake and evenings wind down in a peaceful, private setting. With direct lake frontage, a private pool, and a dock just steps from the house, it’s an easy place to slow down and enjoy Florida lake life.brbrThe home offers comfortable, open living spaces with a natural indoor-outdoor flow, making it ideal for couples, families, or friends spending a few nights together. Spend your days unwinding by the pool, fishing from the dock, or enjoying the quiet rhythm of the lake. Whether you’re here to reconnect, rest, or simply enjoy time outdoors, the setting is calm and unhurried.brbrConveniently located just minutes from Winter Haven, LEGOLAND Florida, grocery stores, and local dining, the home also offers easy access to Central Florida attractions, with Walt Disney World approximately 40 minutes away. It’s the perfect balance of peaceful lake living and nearby conveniences.brbrThis property is currently offered for weekend stays, making it well-suited for short getaways, special occasions, or a refreshing break from everyday life.

Lake Hamilton Oasis - Pool • Dock • Sunrise Views

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$201.63

Pet-Friendly Private Yard | Central Location | Families WelcomebrbrExperience the best of Winter Haven when you stay at this 3-bedroom, 2-bath house. This vacation rental, located near many fun-filled attractions, makes a great home base for groups that want to see the sights. Enjoy a peaceful morning coffee in the sunny breakfast nook before driving to Bok Tower Gardens or even Disney World! At the end of the day, whip up a meal in the kitchen and unwind in front of the Smart TV.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 twin bedbr- Additional Sleeping: 1 queen air mattressbrbrINDOOR LIVINGbr- 2 Smart TVs w/ cable & streaming app (Netflix)br- 2 dining tables, electric fireplacebr- Custom furniturebr- BooksbrbrOUTDOOR LIVINGbr- Lanaibr- YardbrbrKITCHEN br- Stove/oven, refrigerator, dishwasherbr- Dishware/flatware, cooking basicsbr- Drip coffee makerbr- Microwave, blender, rice cooker, toaster ovenbr- Trash bags & paper towelsbrbrGENERAL br- Free WiFibr- Central A/C & heating, heated floors, ceiling fansbr- Washer/dryer & laundry detergentbr- Linens/towels & hair dryerbrbrFAQbr- 1 exterior security camera (facing out)br- Pet fee (paid pre-trip)br- Quiet hours (9:00 PM-7:00 AM)br- On-site maintenance team br- Subdivision renovations (1st week of June 2025)brbrACCESSIBILITYbr- Single-story home, 1 step to enterbrbrPARKINGbr- Driveway (2 vehicles)br- Heated garage (2 vehicles)br- Free street parking (first-come, first-served)br- RV/trailer parking allowed on-sitebr- No parking on grassbrbr-- THE LOCATION --brbr- Close to golf coursesbr- 7-8 miles to LEGOLAND & Peppa Pig Theme Parkbr- 15 miles to Bok Tower Gardensbr- 37 miles to Dinosaur Worldbr- 41 miles to Disney Worldbr- 53 miles to Orlando Int'l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking or vapingbr- Pet friendly w/ $70 fee (+ fees & taxes, 2 pet max)br- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- Please observe quiet hours from 9:00 PM to 7:00 AMbrbrADDITIONAL INFORMATIONbr- This single-story home requires 1 step to enterbr- There is a trailer on the property for the on-site maintenance team br- Major renovations in the subdivision, including gate installation and fencing work on the property lot, will take place in the first week of June br- Your safety matters. This property features 1 exterior security camera located by the front door facing the front entry. It does not look into any interior spaces. The camera records video and sound when activated by motion

8 Mi to Legoland: Winter Haven Home w/ Lanai!

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$510.47

Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor games designed w/ family fun in mind! Only 3 min to charming downtown Winter Haven shopping & restaurants, 10 min to Legoland, 30 min to historic downtown Lakeland, & conveniently located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa). We can't wait for you to enjoy the beautiful lakes of Winter Haven at The Elby! brbrbrThis amazing space boasts over 3,200 sq ft of entertainment, perfect for families and friends looking to make unforgettable memories. Gather in the spacious great room, complete with a huge, down feather-filled sectional couch perfect for movie nights. Challenge your friends to a game of Florida Flamingo Toss, ping pong, foosball or corn hole. Enjoy some friendly competition with a game of wall scrabble, or kick back and relax with the vintage record player. And when it's time to dine, prepare to be impressed by the prettiest dining space you've ever seen! The chef's kitchen is fully equipped with brand new appliances, including a built-in wine refrigerator, blender, mixologists kit, hand mixer, drip & pour-over coffee makers, and all the tools & gadgets you could ever need. Plus, you'll have Sommelier-selected wine glasses, acrylic glass & serve ware for outdoor fun, kids plates, bowls, & utensils, and serve ware for 20+. Come experience The Elby, where luxury and fun collide!brbrbrSleep soundly in our 3 master suites - each w/ a king sized bed & en suite bathroom - plus the bunk room featuring twin bunks & a cozy daybed (that extends to a king bed!) w/ attached 1/2 bath.brbrbrAll bedrooms include:br✔️ brand new modern memory foam mattressesbr✔️ a dedicated workspace (Lego building workspace for the kids)br✔️ smart TVbr✔️ blackout curtainsbrbrbrThe Elby Layout:br1st Floor - 1 master suite w/ full bath, bunk room, 1/2 bath, kitchen, dining, great roombr2nd Floor - 2 master suites w/ full bath in each, balcony w/ seatingbrDetached Garage - game room, laundry room, full bathbrbrbrWe love pets and think traveling with them is more fun! We allow up to 2 dogs to join in on The Elby family vacation with a non-refundable pet rate of $150 per stay. Please no other animals.brbrbrLocation, location, location!br 3 minutes to charming downtown Winter Haven, including our personal favorites: Grove Roots Brewing, Arabellas fine Italian dining, Nutwood, & Obscure Wine Barbr Surrounded by Winter Haven Chain of Lakesbr 10 minutes to Legoland & Cypress Gardensbr 25 minutes to Bok Tower Gardensbr 45 minutes to Disneybr 6 minutes to Venue 650br 9 minutes to Advent Health Fieldhouse & Conference Centerbr 30 minutes to Historic Downtown Lakelandbr Conveniently Located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa)

Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$215.87

Modern 2BR/2BA Apartment – Perfect for LEGOLAND GetawaysbrbrWelcome to your brand-new 2024 luxury apartment, conveniently located on the first floor near the entrance of this gated community. Designed for both comfort and convenience, this 2-bedroom, 2-bathroom unit offers a stylish and family-friendly retreat, just minutes from LEGOLAND.brbrCommunity Amenities:br • Heated resort-style poolbr • Full fitness center & conference roombr • Internet café & coworking spacesbr • Dog park & children’s playgroundbr • Outdoor grills, fire pits & picnic areasbrbrApartment Features:br • Spacious master bedroom with a king-size bedbr • Bunk bed with a pullout trundle in the kids’ roombr • Brand-new Smart TVs in every roombr • LEGO sets, board games & puzzles for family funbr • Fully equipped kitchen with all essential appliancesbr • In-unit washer & dryer for conveniencebrbrWhether you’re visiting LEGOLAND or simply seeking a relaxing escape, this thoughtfully designed apartment offers everything you need for an unforgettable stay.brbrPlease note that this unit is part of an apartment complex, and all VRBO units are located on the first floor for guest convenience and accessibility.brbrBecause of this, there are long-term residents living above you, often with children. Noise levels can vary — kids may be at school during the day, home on weekends, or sometimes home full-time. You may also hear barking dogs or general apartment noise from time to time.brbrWe’ve provided a white noise machine and earplugs in the unit for your comfort.brbrIf the noise becomes excessive and you can identify which apartment it’s coming from (for example, directly above you), please let the office know. Or I’ll contact the main office to report it on your behalf.brbrYou may also reach out to the apartment office directly during normal business hours (7 days a week).brbrIf the disturbance occurs at night, please visit or call the office the next day — they will follow up with the tenants and address the issue.brbrJust a quick reminder: we are guests of this apartment community, and all other residents are long-term tenants. Our unit is one of only two short-term rentals in the entire complex, so your courtesy and understanding are greatly appreciated.br

2-bedroom, 2-bath unit offers a family-friendly retreat just mins from LEGOLAND.

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$227.84

Welcome to the Chain of Lakes Cottage, your refined retreat in the heart of Winter Haven. This elegantly restored cottage offers a serene ambiance perfect for relaxation, yet it's just moments from the area's best lakes and attractions. brbrAs one guest shared, it’s “a great hidden gem! Top-quality linens, kitchen, and bath supplies—felt like a top star hotel in a spacious, welcoming setting.”brbrLuxury and relaxation await at this hidden gem.brbrStep inside to discover thoughtful designer touches throughout. Unwind in the living area on the large sectional sofa in front of the wall-mounted TV. The fully stocked kitchen is a chef's delight, featuring stainless steel appliances and granite countertops, ready for all your cooking and baking needs. The modern bathroom features a spacious, tiled walk-in shower.brbrRest peacefully in one of two oversized bedrooms, each appointed with a comfortable king-sized bed and a TV. For extra coziness, one bedroom includes a charming electric fireplace. This family-friendly cottage is also a perfect getaway for your furry friends, with a private, fenced-in backyard where they can play safely, surrounded by lush landscaping that ensures your privacy.brbr**Key Features:**br* Direct lake access to the beautiful Chain of Lakesbr* Fully equipped kitchen with modern appliancesbr* Onsite washer and dryerbr* Two spacious bedrooms with king bedsbr* Private, fenced backyardbr* High-quality linens and bath suppliesbrbr### Guest AccessbrbrYou will have private access to the entire cottage and the fully fenced backyard. We respect your privacy, so you can enjoy an uninterrupted stay. However, we are always available and happy to assist if you need anything at all.brbr### The NeighborhoodbrbrNestled in a quiet, peaceful neighborhood, the cottage is surrounded by lush greenery. Its prime location right on the Chain of Lakes offers a tranquil escape while keeping you conveniently close to local amenities like grocery stores.brbr### Getting AroundbrbrOur central location makes exploring the best of Central Florida a breeze. You are just a short drive from major attractions, sports complexes, and medical centers.brbr**Local Highlights:**br* Winter Haven Hospital: 5 minutesbr* AdventHealth Fieldhouse & Conference Center: 7 minutesbr* Various Athletic & Softball Complexes: 9 minutesbr* LEGOLAND Florida Resort: 15 minutesbr* Bok Tower Gardens: 35 minutesbrbr**Regional Destinations:**br* Sun 'n Fun Aerospace Expo: 30 minutesbr* Walt Disney World Theme Parks: 45 minutesbr* Orlando International Airport (MCO): 60 minutesbr* Tampa International Airport (TPA): 60 minutesbrbr### Important InformationbrbrPlease note that the detached shed on the property is not accessible to guests.

Modern Comfort, Pet Friendly, 2 King Beds

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$164.01

This lakeside cottage has a peaceful view of Eagle Lake. Close to Legoland resort and an easy drive to many central Florida destinations including Disney World parks, other Orlando destinations, Bok Singing Tower, Tampa beaches, etc. Local community events include free waterski shows and great restaurants. Amenities include high speed internet, flat screen TVs, family dining table and washer/dryer. Smart lock access allows arriving on your own schedule. Rent kayaks with local vendors. Perfect for a family with private driveway and gated yard. Queen master bedroom with twin and trundle beds across the hall, both have adjacent bathrooms. Living room couch can fold out to queen bed to add more sleeping options. Additional activity room on same property and lots of room for parking allows for hosting events. Come discover central Florida at Crystal Beach!

Cottage

Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$207.2

Located in Winter Haven, enjoy what this 3-bedroom home has to offer. With 2 queen beds and 2 twin beds,guests can relax comfortably. Home is warm and inviting and is within walking distance to downtown Winter Haven, Lake Howard and many restaurants.The property features AC, a washing machine, dryer ,WiFi, heating, a hair dryer, and an iron. The 2 bathrooms are equipped with a shower and a hair dryer,and your toiletries needs. Our place is equipped for both long or short stay.br5 minutes to Winter Haven Hospital br6 minutes to advent health field housebr12 minutes to Legolandbr45 minutes to Disney world and Busch gardens adventure park

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

Winter Haven, Florida, United States

3

Bed

Bath

6

Sleeps

$209.81

Winter Haven is waiting for you at this 1-bedroom guesthouse with pool view. A pleasant living room with sofa lounge and plenty of sitting room and a desk and chairs for business stays or working from home along with 65in tv. A Queen air mattress with linen is available for your use that offers awesome relaxation. Enjoy the tranquil bedroom with a comfy queen bed. Guests can unwind in the shower and make use of the hair dryer. You're sure to make fantastic memories with a stay at our place.

Charming 1-bedroom guesthouse with pool view WiFi and AC in Winter Haven

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$187.84

Enjoy the best sunset in Winter Haven on a hammock, then drive 3 mins for dinner downtown. You can't beat this slice of paradise.brbrThis lake home offers two bedrooms with queen beds. Choose between phenomenal views in the lake room, or extra privacy in the master. Comfortable for 4 adults. 2 full baths and a large, fully equipped kitchen are included. brbrDiscounted prices! This is our soft launch. We are still getting the space up to our standards. Furnishings and amenities to be upgraded over the coming months. brbrThe home is decorated and furnished with the owner's personal collection. Please be respectful. We'll make sure you have a fantastic experience. The owner sometimes occupies a separate unit in the back of the property and shares the driveway.brbrPlease note: washer and dryer are not included. There's a smart TV but no cable. We are working on adding these ammenities.

Best sunsets in Winter Haven. Lakefront home 5 minutes from downtown!

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$434.93

We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitchen with granite counter tops, stainless steel appliances, and numerous appliances. The large TV room features a Samsung smart 65 TV that connects to the Lanai/Pool area. A must see to believe!

Fantastic Water Front Home on the Chain of Lakes

Winter Haven, Florida, United States

Bed

Bath

Sleeps

$114.4

Centrally located Modern/Contemporary Spacious Private King Suite that is close to Winter Haven (WH) downtown (2 miles); WH Hospital (2 miles) & LEGOLAND (6 miles). It is perfect for couples+1 kid, solo adventure, or business travelers. This Spacious Private King Suite has a private bathroom (walk-in shower); memory foam King bed; Loveseat Sofa Bed (small convertible futon, folds down for a child); 55 Smart TV; covered parking; W&D, & Kitchenette. Easy check-in, private entrance w/keyless lock.

*CentralLocated*PrivateKingSuitew/Bath, Washer&Dryer(Eagle)

Winter Haven, Florida, United States

Bed