Family-friendly vacation rentals in Lakeland

A serene lakeside view showcases the tranquil waters of Lake Hollingsworth, surrounded by lush greenery and walking paths. Patterns of vegetation are visible along the shoreline, while distant trees line the horizon, creating a peaceful natural landscape.

4.98 out of 5 average rating, 113 reviews

Lakeland LakeFront 4BD|3BA FSC SEU Sun&Fun Tigers

Welcome to Laketitude—your spacious lakefront escape on Lake Hollingsworth! Just steps from Florida Southern College and Frank Lloyd Wright gems, minutes to downtown Lakeland, Sun ’n Fun, and Tiger Town, with Tampa and Orlando only 40 mins away. This 4BR/3BA retreat sleeps 10 and features a large backyard, 65” Smart TV, Xbox, coffee bar, and full kitchen—perfect for families, college visits, and getaways. Don’t miss out on our deep connection with FSC’s rich history- message us to learn more!

Indoor spacesFamilyHeating

The living room features a vintage vinyl record wall that adds character. A spacious white sofa and a brown leather couch are positioned for relaxation. Natural light filters through shuttered windows, illuminating the hardwood floor and a round area rug with a geometric pattern.

4.96 out of 5 average rating, 102 reviews

LKLD Legacy near Downtown Lakeland

The LKLD Legacy is a midcentury ranch, and third generation owned home, in the heart of Lakeland. It's located 5 minutes from downtown, near colleges, and close to I4 exits toward Tampa & Orlando (37mi to Disney, 19mi to Legoland)! The home is in a family-friendly neighborhood and within walking distance to parks and lakes. The large fenced in backyard is perfect for kids and pets (*pet fee required*). Before you leave, snap a photo with the instant camera and add it to our guest photo album!

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4.94 out of 5 average rating, 190 reviews

Cute, Historic District Home - GREAT LOCATION

Enjoy a stylish experience at this centrally-located place 5 mins from downtown Lakeland, 8 mins from I-4, 40 mins from Tampa and Orlando (Disney World/Universal), 1 hour from several beaches including Clearwater. 🐕 Pet friendly but you MUST include your pets in the reservation Nearby places of interest: - Downtown Lakeland - Southeastern University and Florida Southern College - RP Funding Center - Lakeland Linder International Airport - Polk Theatre - Circle B Nature Reserve - and more!

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A quaint green cabin is nestled among tall trees, featuring a sloping roof and large windows that invite natural light. String lights are visible, adding a touch of charm, while the front porch offers a welcoming space for relaxation.

4.88 out of 5 average rating, 160 reviews

The Woodsy Weekender

Take it easy at this unique and tranquil getaway in the woods. Wake up in one of our cozy queen or full sized beds, and enjoy coffee and hot chocolate on the 2nd story deck. 10 minutes from downtown Lakeland, spend your day walking our beautiful lakes and eating at our foodie hotspots. End your day back the at Woodsy Weekender making dinner in our full kitchen and sipping wine on the screened in back porch swings watching the sunset. The perfect little "Safe Haven" cabin for all occasions.

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4.99 out of 5 average rating, 136 reviews

Apartment in Lakeland

Matty’s Citrus Connection

You are going to love this Citrus themed hideaway with its Old Florida feel that takes you back to simpler times. Rest and relax in this backyard paradise while enjoying all that Lakeland has to offer. Whether you choose a relaxing day enjoying the many local activities , take a day trip to a beautiful Florida-beach , or decide to visit one of Florida’s theme parks , this is the place to stay . We are centrally located and have quick access to Polk Pkwy , so your adventures are unlimited .

FamilyKitchenLaundry

5.0 out of 5 average rating, 154 reviews

A bright workspace is showcased with large windows offering views of the lake. Two yellow armchairs sit beside a glass-top table. A desk with a lamp is positioned against the wall, with a potted plant adding a touch of greenery.

Apartment in Lakeland

Romantic Lakefront – Feed Swans – Walkable Dining

Discover SWAN LAKE VACATIONS. Swan elegance meets city charm steps away. Highlights: • Lake Views • Downtown Stroll • King-sized bed • Modern Comfort • Full Kitchen • Semiprivate Patio • Between Tampa & Orlando Why Swan Lake Vacations? • Central Hub • Safety Assurance • Easy drive to beaches and Walt Disney World • Experienced Hosts Escape to Swan Lake Vacations—a place where swans grace the surroundings next to quaint downtown life. Book for a perfect blend of nature and urban comfort!

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The open living area features a comfortable sofa set, a stylish area rug, and large windows allowing natural light to fill the space. An island kitchen with contemporary bar seating and modern appliances is visible, creating a seamless flow between dining and living spaces.

4.98 out of 5 average rating, 181 reviews

Gorgeous Gem in the Heart of Lakeland

LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

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Tiny home in Winter Haven

The indoor area features colorful Lego-themed decor, including a bed covered with a vibrant quilt, and a comfortable sofa with bright cushions. A TV is mounted on the wall. A refrigerator and kitchen area are visible, with a game table and playful rug adding to the lively atmosphere.

4.92 out of 5 average rating, 162 reviews

Tiny Lego Home

Tiny Lego home just 12 minutes from Legoland/Peppa pig. Everything to keep the kids entertained. Massive playground and dining/ grilling area, Large outdoor Lego building area, Indoors every thing Lego. Wall legos, table legos and more. If you like Legos this is the place to stay. The kids will be in Lego heaven! Recently added swimming pool with deck and soccer field in playground area. The outdoor playground park is a shared space for any guests who may be staying at complex.

Indoor spacesKitchenCleanliness

A charming exterior view of the home showcases a well-maintained façade with blue siding and a welcoming front porch. Large windows illuminate the entrance, while a manicured lawn and driveway enhance the inviting curb appeal.

5.0 out of 5 average rating, 109 reviews

Luxury 3BR Near Downtown | Pet Friendly + Peaceful

Luxurious 3-bedroom Lakeland retreat in the peaceful Lake Hunter neighborhood. This beautifully styled home offers modern comforts and Southern charm. Comfortably sleeps 8 guests. Minutes from downtown Lakeland, colleges, and spring training. Features a fully fenced yard, modern kitchen, and family-friendly amenities. Perfect for families, couples, or business travelers seeking a serene escape.

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4.93 out of 5 average rating, 188 reviews

The image captures a serene lake view from a grassy area, with a wooden deck overlooking calm waters. Lush trees frame the scene, providing shade and a natural ambiance. Water lilies are visible on the surface, enhancing the tranquil lakeside setting.

Home in Crystal Lake

Lakefront 3BR/2BA near downtown Lakeland

Welcome to our lake house retreat in Lakeland, Florida. You can enjoy a peaceful getaway with beautiful sunset views and tranquil waters during the evenings, and still visit major cities such as Orlando and Tampa during the day which are less than an hour away. Minutes from Southeastern University, Florida Southern, Lake Hollingsworth, and other attractions in the Lakeland area.

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A single-story yellow house is surrounded by lush greenery, featuring large windows framed by dark shutters. A broad lawn stretches in front, complemented by a mature tree providing shade. The flat roof and symmetrical design contribute to the home's inviting appearance.

4.92 out of 5 average rating, 124 reviews

Charming Lakeland Home

This beautiful home is conventionally located in the middle of Central Florida. 40 minutes from downtown Tampa for a beautiful walk at night, or 50 minutes from all the Orlando parks! Less then 5 minutes from shopping centers, a mall, walmart, etc. Extremely calm and safe area, I-4 not even 5 minutes away. This house is perfect if you plan on exploring everywhere!

KitchenIndoor spacesQuiet

A spacious living area features two gray sofas adorned with patterned throw pillows. A wooden coffee table is centered between them. Soft lighting emanates from table lamps, and large windows allow natural light to fill the room. A dining area is visible in the background.

4.93 out of 5 average rating, 245 reviews

Private Wooded Property 1+ acres with MIL Suite!

1+ Acre property with 4 bedrooms and 3 full baths including a mother-in-law suite. This is perfect for your next getaway including High speed Wifi, Two 4K 55” TV with Nexflix and everything you need for your vacation! If you wish to explore the home is located in a great location with quick access to Parks, Colleges, Airports, and Amusement Parks!

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Popular amenities for Lakeland family-friendly rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 171 reviews

A spacious lawn is framed by large oak trees draped with Spanish moss. Comfortable lounge chairs are positioned facing the tranquil water, creating a serene outdoor space. The lake is visible in the background, enhancing the natural beauty of the setting.

Home in Auburndale

Lake Whistler Beach House with lakefront pool

KitchenIndoor spacesQuiet

Superhost

A colorful bunk bed structure is featured, decorated in vibrant shades of yellow, blue, and orange. The mural backdrop depicts a jungle scene with a leopard and tropical plants, enhancing the playful atmosphere of the room. Spiral staircases offer access to the upper sleeping area.

Townhouse in Davenport

4.94 out of 5 average rating, 139 reviews

WaterPark+Arcade+KingBed+Hot Tub+NearDisney

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4.97 out of 5 average rating, 144 reviews

Home in Davenport

Magical 2 pool-Spa & Game Room Villa near “Disney”

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4.96 out of 5 average rating, 102 reviews

A screened-in pool area features a clear, inviting swimming pool surrounded by comfortable lounge chairs. A basketball hoop is positioned at one end of the pool, with a scenic view of the lake and trees visible through the enclosure.

Home in Haines City

Southern Dunes Lakeview Poolhome

FamilyKitchenLocation

4.99 out of 5 average rating, 159 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

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 150 reviews

A vibrant hallway is adorned with deep blue walls, featuring golden stars and a playful Mickey Mouse theme. A picture of Mickey Mouse in a wizard hat is displayed on the wall, complementing the themed decor. A stylish side table is positioned against the wall.

Villa in Four Corners

Mickey Fantasia Family Friendly w/accessibility

FamilyIndoor spacesAmenities

4.96 out of 5 average rating, 116 reviews

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

FamilyKitchenValue

4.89 out of 5 average rating, 133 reviews

Home in Haines City

Breathtaking Home

Indoor spacesFamilyHot tub

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 214 reviews

Guesthouse in Lakeland

Swan City Studio +Courtyard, mins historic downtwn

KitchenIndoor spacesGrill

5.0 out of 5 average rating, 109 reviews

A welcoming porch features a swing adorned with cushions and a decorative pillow. A vibrant area rug lies underfoot, featuring intricate patterns in hues of blue and coral. Lush greenery and ornamental pumpkins enhance the inviting atmosphere, complemented by a small sign stating 'thankful.'

Cottage in Lakeland

Dixieland Delight

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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

Indoor spacesFamilyValue

4.99 out of 5 average rating, 222 reviews

A cozy living room features a mix of seating options, including a leather sofa and a patterned couch. A coffee table sits centrally on a wooden floor, while large windows allow natural light. Decorative elements include a gas fireplace with a stone surround and a smart TV on the wall.

Bungalow in Lakeland

Historic Downtown Bungalow w/piano

Indoor spacesKitchenNearby

The living area features a comfortable dark sofa adorned with orange pillows. Two lamps provide soft lighting on either side, and a coffee table sits center stage, holding a decorative bowl and a magazine. Natural light filters through the windows framed with blinds.

4.9 out of 5 average rating, 165 reviews

Lake Morton Historical District Home w/ King Bed

Indoor spacesFamilyComfort

4.98 out of 5 average rating, 123 reviews

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.

Home in Winter Haven

Kid-friendly Home w/ Pool & BBQ

FamilyIndoor spacesHospitality

A spacious living area features a sectional sofa with an ottoman and two accent chairs, set on a soft, light rug. A ceiling fan provides cooling, while natural light filters through a large window dressed with sheer curtains. A small side table with a lamp complements the decor.

4.82 out of 5 average rating, 130 reviews

Heart of South Lakeland in adorable neighborhood!

Indoor spacesFamilyDecor

4.97 out of 5 average rating, 236 reviews

A spacious outdoor area is visible, featuring a brick patio that opens towards a calm body of water. Nearby, a wooden dock extends into the water, surrounded by greenery and a few lounge chairs. A peaceful landscape is highlighted by gently waving trees.

Cabin in Haines City

Nearby Legoland,Disney,Universal,Seaworld and more

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Family-friendly home rentals with a pool

5.0 out of 5 average rating, 119 reviews

A bedroom showcases a leafy green accent wall, complemented by a light wood bed frame. Natural wood flooring adds warmth to the space. The bathroom features a modern vanity with dual sinks and a potted plant, while the outdoor area reveals a pool surrounded by a screened enclosure, illuminated by soft blue lighting.

Guest suite in Lakeland

Casa Planta Cozy Tropical Oasis Pool View Suite

Indoor spacesFamilyOutdoor spaces

4.94 out of 5 average rating, 446 reviews

A serene outdoor area features a decorative fountain surrounded by pavers. Lush grass and mulch create a natural border. In the background, a pool reflects sunlight, while lounge chairs and an outdoor seating area are arranged for relaxation.

Guesthouse in Lakeland

Quaint and Charming Pool Cottage....

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The saltwater heated pool is enclosed within a screen patio, surrounded by a well-maintained white fence. Comfortable cushioned seating is visible nearby, along with potted plants adding a touch of greenery. Clear blue skies enhance the peaceful atmosphere of the outdoor space.

4.85 out of 5 average rating, 40 reviews

Relax in Heated Saltwater Pool w/ Screened Lanai

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4.97 out of 5 average rating, 35 reviews

“Relaxing Pool Retreat Near Downtown Lakeland”

FamilyIndoor spacesAir conditioning

A rectangular pool is framed by a stone patio, featuring steps leading into the clear water. Sunlight creates gentle ripples on the surface, while the surrounding screened enclosure offers a view of the lush greenery beyond.

4.83 out of 5 average rating, 81 reviews

Updated home with heated & screened in pool

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4.81 out of 5 average rating, 27 reviews

Welcome to your home away from home!

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4.94 out of 5 average rating, 31 reviews

3/2 Beautiful Pool Home + Garage + Pet Friendly

Indoor spacesFamilyComfort

Superhost