Pet-friendly holiday rentals in Winter Haven

4.98 out of 5 average rating, 166 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!

PetsOutdoor spacesAccuracy

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, 177 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

PetsWalkabilityGetting around

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, 137 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!

Outdoor spacesWalkabilityFamily

Campervan/RV in Lake Wales

A wooden barrel sauna is situated in a serene garden space surrounded by bamboo. The sauna features two benches and a wooden door, with soft lighting highlighting its natural texture and the tranquil atmosphere of the area.

4.81 out of 5 average rating, 150 reviews

Bamboo Bus -Sauna/Pool/Fire pit/Grill

Bamboo Bus is a unique, romantic and tranquil spa like getaway, perfect for relaxing with your significant other, family or friends. Enjoy the pool, unwind in the barrel sauna, grill your favorite meals and gather around the fire pit for s’mores under the stars. Located less than a mile from Lake Pierce, bring your kayaks and explore nearby lakes and state parks. Just 20 mins to LEGOLAND and 50 mins to Disney, it’s the perfect peaceful escape with easy access to Central Florida attractions.

PetsOutdoor spacesCondition

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.

4.95 out of 5 average rating, 101 reviews

Extra large home! Bring Your Boat & all the Toys!

Bring your boat, skis, fishin’ pole, or any other water toys! We supply ping pong, corn hole, bicycles and other toys! Directly across from Lake Howard boat ramp and 10 minutes from LegoLand! Enjoy this spacious, well-equipped 2300 sf home that has everything you need to enjoy your stay in Winter Haven, aka Chain of Lakes City, a quaint downtown with free parking-- and just a skip away from Disney and Universal. This getaway is an above-average accommodation both in style and comfort!

Outdoor spacesWalkabilityAccess

4.99 out of 5 average rating, 129 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.

Outdoor spacesWalkabilityGetting around

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.

4.97 out of 5 average rating, 119 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!

PetsWalkabilityHospitality

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, 348 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.

Outdoor spacesPetsAccuracy

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.

4.92 out of 5 average rating, 219 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.

Outdoor spacesPetsRiver

A charming lake home is showcased with a light-coloured façade and blue shutters. A welcoming entrance is flanked by decorative chairs, with well-maintained landscaping featuring green grass and flower beds enhancing the outdoor appeal.

4.98 out of 5 average rating, 124 reviews

Lake View, Game Room, 10 min Legoland

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!

WalkabilityPetsCheckout

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.

4.97 out of 5 average rating, 147 reviews

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 11 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.

Outdoor spacesWalkabilityNearby

A modern living area features a sectional sofa adorned with blue and white decorative pillows. A round coffee table with a marble top sits on a textured area rug. Natural light fills the space through sheer curtains, complemented by a stylish console table and a round mirror.

4.99 out of 5 average rating, 107 reviews

Cozy 3 bedrooms 2 bathrooms

Relax with the whole family at this peaceful and charming home in Winter Haven.This home is centrally located and is within walking distance to Lake Howard , downtown winter haven and plenty attractions We are located 10 minutes from Legoland, Peppa Pig Park, five minutes to Advent Health Fieldhouse, five minutes to Winterhaven Hospital, 45 minutes to Walt Disney World, SeaWorld and Busch Gardens.

WalkabilityOutdoor spacesHospitality

Popular amenities for Winter Haven pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 25 reviews

Million-Dollar Sunsets Included

WalkabilityDecorAccess

4.99 out of 5 average rating, 107 reviews

Home in Davenport

Pool & Spa Oasis/Golf Retreat/Near Disney/3BR Home

WalkabilityPetsAir conditioning

4.91 out of 5 average rating, 206 reviews

A renovated house is framed by mature trees, displaying a fenced front yard that features a paved walkway leading to the entrance. The structure includes a simple facade with large windows, allowing natural light to enter the interior.

Home in Auburndale

three bedroom family house, near legoland

Outdoor spacesWalkabilityNearby

4.93 out of 5 average rating, 14 reviews

"Chalet" lake house/walking path/fenced yard/dock

PetsWalkabilityView

A modern lakefront home is showcased with a clean, spacious facade. Well-maintained landscaping features palm and leafy plants, complementing the beige exterior. A curved driveway leads to a two-car garage, with panoramic views of the lake apparent beyond the property.

5 out of 5 average rating, 42 reviews

Winter Haven Waterfront Retreat

PetsCleanlinessIndoor spaces

A spacious living area is highlighted by a light-toned sectional sofa and a ceiling fan above. To the side, a dining table accommodates multiple guests, while an open kitchen is visible in the background. Natural light enters through large front doors, enhancing the inviting space.

4.82 out of 5 average rating, 39 reviews

Cozy 3Bed 2Bath Pet-Friendly Home Near Legoland

Outdoor spacesPetsComfort

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, 137 reviews

Legoland Splash Escape (pool and hotub)

PetsOutdoor spacesBathroom

4.98 out of 5 average rating, 200 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

PetsWalkabilityAccuracy

Pet-friendly home rentals with a pool

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.

4.95 out of 5 average rating, 314 reviews

Horse Farm on a Beautiful Lake

PetsOutdoor spacesBreakfast

Apartment in Winter Haven

A circular fire pit area is surrounded by multiple light gray Adirondack chairs on a stone patio. The fire pit is filled with glowing flames, creating a cozy atmosphere against a backdrop of a calm lake at dusk, with soft colors in the sky.

5 out of 5 average rating, 41 reviews

Luxury by Legoland 104

PetsWalkabilityParking

4.94 out of 5 average rating, 217 reviews

A spacious living area features a large sectional sofa arranged around a round coffee table. Bright lights illuminate a modern kitchen equipped with white cabinetry and an island with seating. A ceiling fan is suspended above, enhancing the airy ambiance.

Townhouse in Davenport

Stylish Stay in Davenport

WalkabilityPetsParking

5 out of 5 average rating, 43 reviews

Home in Auburndale

Little Castle on the canal on lake Arietta

Outdoor spacesWi-FiHiking

4.93 out of 5 average rating, 42 reviews

A screened-in pool area features a vibrant pool surrounded by greenery. A comfortable seating arrangement is offered, alongside a grill for outdoor cooking. The pool floats in a sunny yellow design while golf course views are visible in the background.

Home in Haines City

Disney Golf Home with Pool 20 min to Disney!

WalkabilityTVGetting around

4.77 out of 5 average rating, 127 reviews

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.

Home in Davenport

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

WalkabilityPetsIndoor spaces

4.86 out of 5 average rating, 99 reviews

Home in Lake Wales

Lake Retreat w/Pool & Hot Tub near Bok tower

PetsWalkabilityCheck-in

4.98 out of 5 average rating, 121 reviews

Villa in Davenport

Amazing Villa near DisneyWorld FREE heated-pool

Outdoor spacesPetsHospitality

Private, pet-friendly home rentals

4.92 out of 5 average rating, 89 reviews

The Haven House

Outdoor spacesPetsAmenities

4.96 out of 5 average rating, 24 reviews

A serene lakeside sunset is captured, displaying a blend of pink and orange hues across the sky. The still water reflects the vibrant colors, while the silhouette of a dock and a palm tree frame the scene, creating a tranquil atmosphere.

Home in Eagle Lake

30 minutes to Disney and Universal Studios

BikingCheck-inLocation

A spacious bedroom featuring a plush king-sized bed with crisp linens, accentuated by vibrant blue decor. Two large paintings adorn the walls, and a ceiling fan provides comfort. A compact table with lamps stands beside the bed, and a smart TV is mounted in the corner.

4.89 out of 5 average rating, 27 reviews

Travelers Haven

Outdoor spacesComfortAmenities

4.67 out of 5 average rating, 73 reviews

A cottage home is nestled among trees, featuring a welcoming front porch with large windows. The surrounding yard is spacious and marked by a gravel path, providing a sense of openness, while a wooden fence outlines the property.

Home in Eagle Lake

Quaint Cottage, 6 miles to Legoland, Pet friendly!

PetsOutdoor spacesLayout

4.99 out of 5 average rating, 84 reviews

Home in Lakeland

Karen’s Happy House

WalkabilityOutdoor spacesAmenities

4.93 out of 5 average rating, 86 reviews

Arcade+Pingpong + 10 guests + 11 mil to Lego Land!

PetsWalkabilityLong stay

4.79 out of 5 average rating, 42 reviews

A screened lanai features a private heated pool surrounded by lounge chairs. A serene sunset casts a warm glow over the distant trees and lake, creating a tranquil setting for relaxation.

Home in Haines City

Lakefront HOME•POOL•Pet Friendly•Golf Course!

WalkabilityOutdoor spacesBathroom