Family-friendly holiday 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!

KitchenFamilyLayout

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!

FamilyKitchenBathroom

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!

Indoor spacesFamilyLong stay

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.

FamilyIndoor spacesParks

4.99 out of 5 average rating, 135 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 .

FamilyIndoor spacesCleanliness

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!

FamilyKitchenQuiet

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, 180 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!

FamilyIndoor spacesLocation

4.91 out of 5 average rating, 150 reviews

Studio apt in Historic area of Lakeland

This second story studio is on our homes property. It has a Queen bed, bathroom and kitchen. It is nestled in the historic area of Lakeland, one block in from The "Frank Lloyd Wright" designed Florida Southern college, tours are available! Our Cobblestone streets take you to our neighborhood restaurants, the art museum, library, Hollis garden, we are between two lakes-Hollingsworth it has a great walking/running path, and Lake Morton a bird paradise. All within walking distance.

Indoor spacesKitchenNearby

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.

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.

KitchenIndoor spacesParks

4.92 out of 5 average rating, 162 reviews

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, 108 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.

KitchenIndoor spacesCheck-in

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!

FamilyKitchenCleanliness

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

Dixieland Delight is a cute 1920's bungalow that has been update with all the modern features while keeping all the historical features that make this home so special. It is within walking distance to restaurants and shops as well as lakeland's beautiful lakes. Downtown Lakeland is only one mile away. The newly opened Bonnet Springs is only 1.5 miles.

FamilyIndoor spacesSleep quality

Popular amenities for Lakeland family-friendly rentals

Kitchen

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

FamilyIndoor spacesCheckout

4.97 out of 5 average rating, 144 reviews

Home in Davenport

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

FamilyKitchenBackyard

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

WaterPark+Arcade+KingBed+Hot Tub+NearDisney

KitchenIndoor spacesHot tub

4.94 out of 5 average rating, 139 reviews

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

KitchenFamilyLong stay

4.99 out of 5 average rating, 158 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

KitchenFamilyGetting around

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

FamilyKitchenAccuracy

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

KitchenIndoor spacesAir conditioning

4.9 out of 5 average rating, 106 reviews

Townhouse in Davenport

Special Offer Resort style & free Waterpark 1150

FamilyKitchenBarbecue

Family- and pet-friendly home rentals

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 spacesFamilyTV

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 spacesKitchenSleep quality

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.

Horse Farm on a Beautiful Lake

FamilyIndoor spacesNearby

4.95 out of 5 average rating, 314 reviews

4.94 out of 5 average rating, 214 reviews

Swan City Studio +Courtyard, mins historic downtwn

KitchenIndoor spacesAccuracy

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!

FamilyKitchenCheckout

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

Indoor spacesKitchenNearby

A charming exterior of the detached suite is framed by lush greenery and colorful landscaping. A patio area with a table and four chairs is visible, along with a sun umbrella. Soft lighting enhances the welcoming ambiance during the twilight hours.

4.98 out of 5 average rating, 116 reviews

Serenity at Success

FamilyIndoor spacesParking

4.99 out of 5 average rating, 115 reviews

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.

Home in Winter Haven

Cozy 3 bedrooms 2 bathrooms

Indoor spacesFamilyWi-Fi

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

KitchenIndoor spacesQuiet

4.95 out of 5 average rating, 169 reviews

A spacious living area is presented with a sectional sofa, a wooden coffee table, and a wall-mounted television. Large windows allow natural light and views of the outdoor patio. The room features light-colored walls and art pieces that add a modern touch.

Home in Cypress Gardens

Unique Glass House/ 7 Min Legoland/ Sleeps 7

FamilyKitchenBackyard

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.

4.94 out of 5 average rating, 446 reviews

Quaint and Charming Pool Cottage....

KitchenFamilyAccuracy

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, 39 reviews

Relax in Heated Saltwater Pool w/ Screened Lanai

KitchenFamilyWi-Fi

4.97 out of 5 average rating, 35 reviews

“Relaxing Pool Retreat Near Downtown Lakeland”

FamilyKitchenPool

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

Indoor spacesFamilyCheckout

Superhost

4.81 out of 5 average rating, 27 reviews

Welcome to your home away from home!

FamilyKitchenPool

A modern kitchen and dining area feature glossy white cabinetry and sleek stainless steel appliances. A large island with three stools provides ample workspace, while a dining table with high-backed chairs accommodates several guests. Natural light streams through the windows, enhancing the bright and open feel.