Pet-friendly vacation rentals in Winter Haven

4.97 out of 5 average rating, 152 reviews

An inviting living area features a comfortable tufted chaise lounge and a cozy recliner. A flat-screen TV is mounted above a classic fireplace, surrounded by soft curtains that frame bright windows. The floor showcases warm wooden tones, contributing to a homely ambiance.

Cottage in Lake Wales

Charming, renovated 1917 Cottage

Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!

A cozy living area features a light brown sectional sofa and a matching sofa adorned with patterned cushions. A modern coffee table sits in the center, with a remote control placed on top. A large artwork of a character hangs above, flanked by two lamps.

4.89 out of 5 average rating, 131 reviews

Heated pool/hot tub, near Legoland, Disney,

Relax in the heated pool and hot tub after enjoying theme parks such as Busch Gardens, Disney world, and Universal Studios! LegoLand is 1 mile away! Lego bedroom for kids. Centrally Located in the middle of Florida allows beach trips to both east & west coast. air conditioned garage has been turned into a game room pool table, air hockey and a miss pac-man arcade game! Private boat & RV parking with RV outlet thru gate in backyard. Pool can be heated to 85 degrees for a small fee if $10/ day

Home in Downtown Winter Haven

A well-lit living room features a comfortable gray sofa and a light pink chair. A round coffee table is centered on a soft rug, while a contemporary TV stand holds a flat-screen television. Large windows provide natural light, and a door leads outside.

4.9 out of 5 average rating, 164 reviews

3/2 Great Family Home Near Legoland

Enjoy easy access to Legoland (4 mi) & charming Downtown (1 mi) from this centrally-located home. Designed to make you feel right at home during your family getaway, the whole home is private to you. We are pet friendly! Featuring a kitchen ready to make a home meal, a fully fenced private back yard, keyless entry, & free, ample parking for multiple cars and a trailer. Street parking is also allowed. Locally owned & operated. We are excited to share our city and provide exceptional service

Guest suite in Winter Haven

Three thoroughbred horses graze peacefully on a lush green pasture. The area is surrounded by tall trees, providing shade and a natural backdrop. A glimpse of a trailer can be seen in the background, indicating the farm's working environment.

4.96 out of 5 average rating, 301 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. The dock has plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door. Please note there is no barrier around pool and all children (anyone under age of 18)must be supervised at all times. Guests must swim at their own risk. You may see horses in the paddocks. The pool deck overlooks the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

The exterior of a spacious home is presented, featuring a blue façade and a welcoming entrance. Lush tropical foliage surrounds the property, which is highlighted by palm trees and manicured lawns. A vibrant sunset casts colorful hues in the sky, enhancing the serene atmosphere.

4.98 out of 5 average rating, 131 reviews

Spectacular Waterfront Home in Winter Haven

Enjoy a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. Featuring a chef's kitchen, 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest. We are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary!

4.99 out of 5 average rating, 116 reviews

A charming white cottage is framed by a well-kept lawn, with a brick chimney visible on one side. Lush green shrubs and trees provide shade around the property, and a pathway leads to the entrance, suggesting easy access to the home.

Cottage in Davenport

Classic Cottage in country setting

Relax with the family in this peaceful setting. Short drive to the parks, shopping, restaurants. 10 minutes from Interstate 4. Walmart and Posner Park Shopping Center nearby. Patio area with fire pit and gas grill and lawn chairs. 2 car carport parking on premise. 2 bedroom w/HDTV's, 2 bath, fully furnished kitchen, dishwasher, breakfast nook, dining room, living room w/HDTV. Washer/dryer. Fully fenced 3/4 acre yard with plenty of room for kids to play. Self check in with keypad.

A large outdoor space features a private pool surrounded by loungers in blue and a shaded dining area. A patio table with chairs is placed in the foreground, while a safety fence encloses the pool area, providing a secure environment.

4.98 out of 5 average rating, 104 reviews

Kid-friendly Home w/ Pool & BBQ

Enjoy a delightful stay in our Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, washer, Wi-Fi, fully equipped kitchen, baby proofed, and BBQ to make your stay comfortable. Enjoy the private pool, free parking, and large patio. Our house is 20 mins away from LEGOLAND and 50 mins away from Disney Parks and attractions. Discover Winter Haven’s chain of lakes with all the water sports and its surroundings in the best way. We look forward to hosting you!

A serene lakeside view is observed, featuring gently swaying palm trees on the left and a wooden dock extending into the water. A boat is anchored at the dock, surrounded by lush greenery and a clear blue sky.

4.95 out of 5 average rating, 111 reviews

Lakefront Home on the Winter Haven Chain O’Lakes!

Completely renovated 2 Bedroom, 1.5 bath home location on beautiful Lake Roy on the Winter Haven Chain O’Lakes. This is a mother-in-law suite that is connected to the main home. One bedroom on the lower level with a queen bed. Second story with king bed and twin bed. Full bath located upstairs). Comfortably sleeps 5. Dog welcome with prior approval and pet fee. Boat parking at dock. Boat rental available at Central Florida Water Sports. Private entry with keyless touchpad.

A serene backyard features a clear swimming pool surrounded by a tiled deck. Sun loungers are positioned around the pool, with a shaded dining area beneath a striped umbrella. Lush greenery and tall trees provide a natural backdrop, enhancing the outdoor space.

4.78 out of 5 average rating, 337 reviews

Florida Oasis w/ Pool near LEGOLAND

We have added a modern twist to the design of this 1950's home with all the modern appliances and finishes. This home is nestled in-between 2 lakes among the Winter Haven Chain of Lakes! The backyard is a Florida Oasis of a great pool and pool deck with plenty of fun available with games for you and the kids, or just enjoy laying peacefully in the sun! 2.5 mile drive from Legoland 3.5 mile drive from Downtown Winter Haven with great restaurants and small town unique shops.

4.97 out of 5 average rating, 171 reviews

The house exterior displays a blend of white wooden siding and warm wooden accents. Two white, vintage-style chairs are positioned on the porch, leading to a central door with decorative glass. A small set of stairs provides access to the entrance.

Home in Lake Wales

Linda Casita de Lake Wales

Cute older house with modern amenities. Located right downtown within a block from the playpark, Lake Wailes lake, walking path, and the historic downtown shopping area. All of the appliances in the home are brand new, as well as the washer and dryer. There is a large TV in the living room, as well as one in each bedroom - each with Roku and Netflix. Each bedroom also has a mini split A/C unit to sleep as cold, or hot, as you like. Parking is in the rear covered carport.

An inviting swimming pool is surrounded by a spacious patio area, featuring lounge chairs and a shaded table with an umbrella. The serene view of Little Lake Otis and lush greenery is visible in the background under a partly cloudy sky.

4.91 out of 5 average rating, 204 reviews

Legoland Lakehouse Canoe & Kayak Retreat

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

A private backyard features a clean in-ground pool surrounded by a paved patio. Two lounge chairs are positioned beside the pool, and a dining set with four chairs sits nearby. Lush greenery and a white privacy fence enhance the serene outdoor setting.

4.98 out of 5 average rating, 126 reviews

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 10 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.

Popular amenities for Winter Haven pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly home rentals with a pool

4.99 out of 5 average rating, 137 reviews

The Tiny House is situated in a serene outdoor setting, featuring a light-blue exterior with a metal roof. A wooden porch with rocking chairs extends at the front, while the surrounding landscape includes lush green grass and landscaping along a gravel path.

Tiny home in Lakeland

Charming Tiny House on 5 acres with POOL/ HOT TUB

4.91 out of 5 average rating, 231 reviews

A spacious outdoor pool area is highlighted by a private sparkling pool surrounded by a sunbathing deck. Modern outdoor furniture, including a dining table and lounge seating, is arranged for relaxation. A grill is visible, perfect for outdoor cooking under an inviting sunshade.

Home in Orlando

Amazing Pool • Huge Yard • 5 Min Universal

Apartment in Winter Haven

An outdoor fire pit is surrounded by several wooden Adirondack chairs on a patio. The flames flicker brightly, reflecting in the water beyond, which is visible under a soft sunset glow. A serene landscape is framed by a black railing.

4.96 out of 5 average rating, 28 reviews

Luxury by Legoland 106

4.89 out of 5 average rating, 102 reviews

A private pool and spa area is enclosed by a screen, offering views of a serene sunset through palm trees. The pool features a textured surface and a safety railing, with vibrant water reflecting the evening sky. A lush green lawn surrounds the space, contributing to the tranquil environment.

Villa in Davenport

25%off/Close to Disney/Hot Tub/Private Pool/Fenced

A serene bedroom is showcased, featuring two unique boat-shaped beds with wooden accents. A large mural of a scenic lake and mountains enhances the space, while natural light filters in through the window, framed by white curtains. A ceiling fan adds a cool breeze.

4.91 out of 5 average rating, 78 reviews

Stylish Lakehome w.HUGE Pool/Arcade/Theater

An inviting outdoor space features a gently curving pool with a built-in hot tub, surrounded by a screened enclosure. Comfortable lounge chairs are arranged nearby, with two patterned hammocks and a dining area visible in the background. Soft evening colors fill the sky above.

4.79 out of 5 average rating, 123 reviews

There is no other place you want to be than here.

4.88 out of 5 average rating, 89 reviews

Home in Lake Wales

Lake Retreat w/Pool & Hot Tub near Bok tower

4.99 out of 5 average rating, 104 reviews

Villa in Davenport

Amazing Villa near DisneyWorld FREE heated-pool

Pet-friendly home rentals with a hot tub

4.97 out of 5 average rating, 33 reviews

Home in Auburndale

King Bed Suite, Fireside Hot Tub, Gameroom

4.89 out of 5 average rating, 99 reviews

Condo in Davenport

The thrill of luxurious living just 15 min/Disney!

4.99 out of 5 average rating, 146 reviews

A private pool area is illuminated in a soft green hue, surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, with a table set under an umbrella. String lights create a warm ambiance as the evening sky darkens.

Villa in Davenport

Magical Disney House-Pool & Hot Tub,Free Waterpark

4.97 out of 5 average rating, 430 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Condo in Orlando

Waterfront Condo minutes to Disney & Universal

4.88 out of 5 average rating, 135 reviews

Camille's Family Guest Home.

4.8 out of 5 average rating, 176 reviews

20 mins to Disney | Private Pool & Spa | 4BR Home

4.91 out of 5 average rating, 334 reviews

The interior showcases a spacious living area featuring contemporary furniture in neutral tones. A large dining table is centrally placed, and natural light filters through expansive windows, enhancing the openness of the space. The enclosed area includes a view of a private pool and hot spa.

Home in Orlando

Mid-century Modern Villa w/ Pool Near Universal

Townhouse in Highlands Reserve

A themed bedroom inspired by 'Nightmare Before Christmas' features a decorative mural with a crescent moon and whimsical trees. The bed is adorned with vibrant bedding, and a warm light illuminates the room. A closet area displays themed decorations, enhancing the enchanting atmosphere.

4.93 out of 5 average rating, 119 reviews

LazyRiverWaterPark+KingBd+Arcade+Water Park+HotTub

Pet-friendly house rentals

4.95 out of 5 average rating, 20 reviews

A serene waterfront view captures a vibrant sunset reflected on the lake's surface. Silhouetted palm fronds frame the scene, while a wooden dock extends into the water, creating a peaceful atmosphere for relaxation and contemplation.

Home in Eagle Lake

30 minutes to Disney and Universal Studios

4.93 out of 5 average rating, 45 reviews

An enclosed swimming pool area is surrounded by a spacious screen enclosure, providing a clear view of lush greenery and a privacy fence in the background. Sunlight streams in, creating a bright and inviting atmosphere, while potted plants add touches of color around the pool's edge.

Home in Auburndale

Florida Oasis

Home in Downtown Winter Haven

A cozy loft bedroom features a spacious bed with soft linens and decorative pillows. A Roku screen projector casts images onto the slanted ceiling. Light from recessed fixtures brightens the room, while minimalist decor includes two small plants and a white dresser against the wall.

4.92 out of 5 average rating, 52 reviews

Lake House by Legoland + Loft & Private Dock

5 out of 5 average rating, 3 reviews

Pretty House Near Disney

4.61 out of 5 average rating, 18 reviews

The entrance of a charming house is framed by landscaped greenery and a neatly trimmed lawn. A tall palm tree stands beside the front door, which is accented by light fixtures and a welcoming blue hue. The clear sky adds to the inviting ambiance.

Home in Haines City

Spacious 4BR Retreat with Heated Pool! Near Parks!

4.98 out of 5 average rating, 58 reviews

Home in Edgewood

Karen’s Happy House

4.9 out of 5 average rating, 10 reviews

Spacious Winter Haven Retreat w/Pool&Pet Friendly!

An aerial view of a single-story home is presented, showcasing a well-maintained lawn and driveway. The surrounding neighborhood features a mix of greenery and residential structures, contributing to a welcoming suburban atmosphere.