Home Vacation Home Rentals By Owner In Winter Haven, FL

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Exceptional(11)

$385.0

/ Nightly
Private Vacation Home

Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome

Winter Haven, Florida, United States

***NO LOCAL GUESTS*** RESERVATIONS OF MORE THAN 6 people not accepted. Property max capacity is 6 people, One of the very few Stylish stays in Winter haven. Only 5 min to Legoland, 40 min from Busch Gardens, and 40 min from Disney. CENTRALLY LOCATED, 5 minutes from Wal-Mart and near (within 5-10 minutes) all major shopping stores. This newly renovated TRI-level lakefront home has a huge HEATED pool (heated at an additional cost of $100 per day), in home theater, and arcade with a PS5! Close to restaurants & shopping. Our attention to detail and style is unmatched. We love providing luxury accommodations for our guest. Please note: The pool heater is available at an additional $100 per day. Request for pool heater must be done for entire stay, no partial stay request for pool heater as it takes up to 24hrs to reach the desired temperature. While we are a pet friendly home, a pet fee of $250 is required for all reservations including a pet. Rules for pets during stay are as follows:brPets must be leashed on property.brPick up after dog.brDogs to stay off furniture and/or bed. brDon't leave animals unsupervised.brPets must be housebroken.brAnimals sometimes tend to bite and claw at things when they are in unfamiliar areas. Therefore, if a pet is to be left alone indoors, it must be crated no exceptions.
Bed 3

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Bath 2

Bath

Sleep 7

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$512.0

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Private Vacation Home

An Amazing Mid-Century Modern Experience

Winter Haven, Florida, United States

Welcome to The Gene Leedy House, the life-long residence of iconic architect, Gene Leedy. A founding member of the Sarasota School of Architecture, Gene moved to Winter Haven, FL in 1954 and began to leave his mark on the small, citrus town, now known to locals as “Leedy Land”. One of his first projects, which would later be historically recognized as the “Craney Spec Homes”, consisted of eleven mid-century modern homes built on a crest between an existing Grapefruit grove and Lake Elbert. At the time, Gene’s modern design was deemed radical for its use of open floor plans, lack of ornamentation, exposed framing, sliding glass doors used as walls, and use of common, “honest” materials in uncommon ways. These elements, which are now commonplace in modern design, helped establish Gene and the Sarasota School of Architecture’s lasting legacy on modern architecture and explains why he occupied the home for over sixty years.brAfter Gene’s passing in 2019, the residence was purchased by architect and long-time family friend, Max Strang. Max, who spent many of his younger years visiting the house, realized the opportunity to honor his former mentor and restore the residence back to its previous state. While the property has undergone many changes, Max’s vision for the property was to not only rehabilitate, but restore many of the elements that were present in the original design. While some new touches have been made, you’ll find even more original elements restored, including most of the iconic furniture that’s been in the home for over sixty years. brbrThis listing represents a truly unique opportunity to stay in the home of one of Florida’s most revered modern architects. Please note that this home was originally built in 1957 and is on the National Historic Register. Guests are encouraged to take this under consideration before booking this home.brbrThe home features two separate “wings”. The Main Wing is comprised of the Living Room, Dining Area, Kitchen, Bar/Library and two bedrooms. The Main Bedroom suite features a bedroom, attached office, bathroom and courtyard patios. There is another small bedroom with a bathroom across the hall.brbrThe North Wing is located across the courtyard and functions well as a private suite with a bedroom, bathroom and lounge. The lounge has a sofa bed and can be closed off to be used as a private bedroom if needed.
Bed 4

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Bath 1

Bath

Sleep 6

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Exceptional(8)

$199.26

/ Nightly
Private Vacation Home

Modern Comfort, Pet Friendly, 2 King Beds

Winter Haven, Florida, United States

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.
Bed 2

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Bath 1

Bath

Sleep 5

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Exceptional(28)

$323.37

/ Nightly
Private Vacation Home

Lakefront Winter Haven Retreat: Hot Tub & Patio!

Winter Haven, Florida, United States

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
Bed 4

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Bath 3

Bath

Sleep 22

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Exceptional(12)

$470.4

/ Nightly
Private Vacation Home

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

Winter Haven, Florida, United States

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)
Bed 4

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Bath 4

Bath

Sleep 11

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Exceptional(28)

$304.49

/ Nightly
Private Vacation Home

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Winter Haven, Florida, United States

About this spacebrThis stylish place to stay is perfect for vacation. With 2 ensuite bedrooms plus 2 additional rooms and 2 additional semi private sleeping areas there is room for everyone. Every space is newly furnished with stylish pieces and comfortable beds. The pool area is fully screened in so you can enjoy the Florida weather without the bugs. The open concept space is perfect for large groups and families and the kitchen is ready for you to make a meal. A laundry room houses a washer and dryer.brThe spacebrThere are 4 bedrooms. At the front of the house french doors open to a space that includes 2 bedrooms with queen beds, a bathroom and a playroom with a twin bed (this room is not private but we've placed a room divider by the bed. There is also a shared full bathroom with double sinks.brbrLocated at back of the house, off the open concept living room is the first and largest ensuite bedroom with a king bed and large full bathroom with separate shower and tub. A sliding door opens to the screened in pool deck. We have two stackable twin beds for little ones to sleep on in this room or use it as a daybed for reading. The walls were built with extra sound proofing so that late night, living room, movie watching or early morning, pancake making won't disrupt sleep.brbrOn the other side of the house off the dining room is the second ensuite with a queen bed and private bathroom. There is a door in the bathroom leading to the screened in pool deck. A large window in the room overlooks the pool.brbrIn each room you will find ample closet space, ceiling fans, extra pillows and blankets. And plenty of towels! No one towel person for an entire stay here!!brbrThe living space is open concept with 3 sliders leading to the screened in pool. Ample space to move around and enjoy each others company. Sectional sofa and a smart tv in the living room, you can sign in to your own streaming accounts. The dining table seats 8 (one side is a bench so extra kids can squeeze in if needed, and there is room to pull up extra chairs) and the large kitchen island seats 4. There is another table and chairs on the pool deck.brbrThere is a large dedicated desk space with granite counter tops and an office chair. Pencils, pens, crayons, etc in the drawers.brbrThe pool is not heated, most of the year it is comfortable but in the coldest winter months it can be pretty cold. There is a covered lanai with seating and have I mentioned that the entire space is screened in Extra pool towels are located in the laundry room, we ask that you wash and put away your own pool towels. A propane grill and yard games are located on the pool deck. The back yard is private.brbrGames galore are located in the front playroom closet.brbrThere is room in the driveway for 4 cars. Street parking is allowed.brGuest accessbrYou'll have access the entire home but not the garage.brOther things to notebrNo parties. We love our neighbors and ask that you respect that this is a family neighborhood. No guests outside of the reservation without permission. No excessive noise.brbrNo smoking in the home or the screened pool deck. Please dispose of cigarette butts properly and not in the yard.
Bed 4

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Bath 3

Bath

Sleep 11

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Exceptional(27)

$901.27

/ Nightly
Private Vacation Home

Spectacular Waterfront Home in Winter Haven

Winter Haven, Florida, United States

HIGHLIGHTSbr+Custom built in 2006 br+Chef’s kitchen with Viking Professional appliancesbr+Waterfront on 3 sides of the property!br+2 docks with boat cleats - bring your boat!br+Beautifully manicured grounds - all new lakeside landscapingbr+Screen enclosed Florida Pool with hot tubbr+Additional waterfront above ground hot tubbr+West facing for fabulous sunsetsbr+Covered parking for 2 vehiclesbr+Upstairs and downstairs screened porchesbr+TVs in every roombrbrCONVENIENCES:brbrInterior:brbrSpanning over 3000 square feet, the interior has a relaxed and open floor plan with 2-story soaring ceilings, a spacious great room, wall-to-wall French doors and lower/upper screened porches for enjoying the amazing lakefront setting and sunsets.brbrThe Great Room is filled with beautiful furniture, decorations and artwork that provide an ambiance of tropical relaxation and belonging.brbrThe chef’s kitchen is designed for entertaining with Viking Professional Series appliances featuring a 6-burner stove, two raised bars/buffets, granite slab countertops, and a custom pounded copper farm sink with unobstructed lake views.brbrThe laundry room features raised front loading GE washer and dryer with a separate sink.brbrbr4 RoomsbrbrPrivate Master Suite: the entire upper level is yours for luxurious living with a comfy king bed, private sunset balcony (with chairs and a table), California style walk-in closet, relaxing master bath with soaking tub, walk-in shower and double sink granite vanity.brbrOur 3 downstairs rooms are themed to reflect to the unique location on Lake Eloise, the Water Ski Capital of the World, and former home of Cypress Gardens. br br“Lake Room”: Queen bed overlooking the lake with direct access to downstairs patio.brbr“Ski Room”: 2 “day beds” that each easily convert to 2 King beds. Playful tropical colors with a water ski theme. Walk in closet inside Jack and Jill bathroom.brbrThe Lake Room and Ski Room share a “Jack and Jill” bathroom with separate tub, walk in shower, and double sinksbrbrGarden Room: Queen bed with private bathroom and showerbrbrAll bedrooms rooms have TVs and luggage racksbrbrExteriorbrbrThe property is a tropical paradise with plenty of room for playing and relaxing.brbrSurrounded by water, not neighbors.brbrOur Caribbean style entrance features a Red Door, the multicultural sign of welcome and warmth. Pineapples, a symbol of Southern Hospitality, are placed inside and out to garner good cheer, human warmth, and family affection.brbrOur two docks are now available for your pleasure. The main dock features a large covered bar area with plenty of seating. It’s a perfect place for entertaining or just hanging out while enjoying the breathtaking lake views in style. The main dock also features a large uncovered area for fun in the sun. brbrThe jewel of the dock is our lakeside jacuzzi – relax amidst our signature cypress trees that rise from the lake, just feet away. Marvel at magnificent views of nature at its best. brbrbrGet set for outdoor living where you can use our 36Blackstone griddle or grill out or relax in our Adirondack chairs or comfy 2 person swinging chairs. Bring 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 lake for the sport. If angling is your style, cast and reel on 18 connected lakes for a great fish story.brbrNearly 1-acre of grounds are masterfully manicured with majestic cypress trees, flax, pineapple, citrus, a wide variety of palms, and much more.brbrTake satisfaction knowing you're living your best life at our waterfront oasis. This is a place you won’t want to leave!brbrFor more info, links, and photos follow our facebook page “Cypress Gardens Lake House”brbrOur Story – by Tony KlarichbrbrDid you know that Lake Eloise is the world’s most famous site for water skiing Dick Pope, Sr. came here in the 1930s and founded Cypress Gardens, Florida’s first theme park. A decades long ski show became the thrilling centerpiece of Pope’s park. To promote his tropical paradise, Pope plied the media with tens of thousands of images of beautiful young men and women in bathing suits skimming across the water.brbrPope’s promotions worked, and millions made the trek to Cypress Gardens including Elvis, Betty Grable, King Hussein of Jordan, multiple Miss Americas, and numerous stars of stage and screen.brbrPope inspired me too. I was recently inducted in the Water Skiing Hall of Fame, and like many before was attracted to the “Water Skiing Capital of the World” all the way from California. It has been a long time dream of mine to retire in Florida near Cypress Gardens to build on Pope’s legacy in towed watersports. We are only here part time, so we are sharing our space with our space with you.brbrIn the meantime my wife and I are using this beautiful home as a base of operations to co-produce the Wake-Ski 100, the Centennial Celebration of Towed Watersports in 2022 to be hosted just 15 miles away at the Lake Myrtle Sports complex. You will be a part of this legacy too, when you stay at our home. History has been made on this lake, and much more is to come.brbrEvent InfobrMaximum overnight guests is 10 unless pre approved by ownerbrDay Guests = less than 4 hours on property. Fee= $15/day guest per day (4 hours)brAdditional late fees for overnight or day guests not booked or pre-approved.brEvent fees & additional requirements for 15+ guestsbrEvent insurance for 15+ guests is required (we have a contact)brOutside services and vendors are not permittedbrOnsite parking on driveway or lawn outside fencebrMonitored by outside security cameras: Ring Devices (6): Front Door, Carport, Front Driveway, Back Patio, Side Door, Enclosed Hut Covering Main Dock. All cameras record at all times.brWARNING: Do not disable, cover, redirect or tamper with cameras. If you do, someone will come to restore cameras and inspect the property AT YOUR EXPENSE.br breaking these rules results in report to VRBO + loss of security deposit and/or additional fees
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

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