Family-friendly holiday rentals in Wesley Chapel

4.97 out of 5 average rating, 115 reviews

A modern single-story home is set amidst lush grass and tropical landscaping. Palm trees frame the structure, which features a clean exterior and large windows. The driveway leads to a two-car garage, enhancing the home’s welcoming curb appeal.

Home in New Tampa

Poolside Paradise Retreat-spacious 4 bedroom home!

Welcome to The Poolside Retreat! Bring the family, unwind, & have fun at our modern Tampa home, located just a short distance away from beautiful downtown Tampa and other local attractions. If you are looking for a spacious place to stay that incorporates the perfect mix of indoor and outdoor fun, look no further. 4 bedrooms to accommodate 8 guests with fully stocked kitchen and outdoor bar/grilling area. Outside you will find a pool (heated during winter), outdoor seating and covered patio.

4.98 out of 5 average rating, 134 reviews

A spacious game room features a blue felt pool table and a foosball table, providing ample entertainment options. The room is well-lit with overhead lighting and includes a wall-mounted television, ensuring a lively atmosphere for games and relaxation.

Home in Lutz

Entire House with Game Room in Lutz - near Tampa

Entire house with a Game Room equipped with a pool table and a foosball table. Designated working area in Master Bedroom. One King Bed, one Queen Bed and two Twin Beds to accommodate a group of up to six people. A TV in each bedroom, living room and game room. Easy access to USF, Busch Gardens, restaurants, malls and beaches. Short distance to Tampa Premium Outlets and Advent Health Center Ice. Playground, Community Pool, Basketball and Tennis Courts are conveniently located across the street.

4.9 out of 5 average rating, 113 reviews

A donkey with large ears and a gentle expression stands close to a fence. Green grass and trees create a tranquil rural background, while a pig can be seen in the distance, adding to the farm-like atmosphere.

Tiny home in Dade City

Dade City Farm Stay

A prime location for bikers and cycling with some of the only rolling hills in Florida. 30 minutes from Tampa attractions: Busch Gardens, Tampa Premium Outlets, Straz Center, ZooTampa. Local attractions: Giraffe Ranch, Kumquat Festival. Down the road is Snow Cat Ridge, Tree Hoppers, Scream-a-geddon. A rural place with a charming downtown scattered with unique eats and antique shops. Get away from it all while making memories on our farm. Enjoy our animals on your stay! Camel, ostrich and more!

4.78 out of 5 average rating, 116 reviews

A serene terrace scene showcases a small table set with a wine bottle and two glasses, framed by two aqua-colored chairs. The calm lake reflects a vibrant sunset, while palm trees outline the horizon in the distance. A flock of birds is seen flying across the sky.

Condo in Zephyrhills

Breathtaking Sunset - Renovated Studio Saddlebrook

Relax in this fully Renovated large Studio, in the highly desirable SADDLEBROOK Golf & Tennis RESORT. The sudio features a beautiful terrace just on the lake with AMAZING VIEWS of the lake and golf green. For your comfort, a Queen bed with new mattress, a nice size kitchenette with: Refrigirator, Microwave, Large toaster-oven, coffee maker and sink. The Studio also offers a dining area, work space, and walk-in closet, as well as Wifi & Cable TV. In the Resort local restaurants and Pub.

A two-story farmhouse with a light green exterior is positioned amidst trees. A covered porch with black railings and steps provides access to the front door. Gravel pathways lead to the home, enhancing the rural setting.

4.97 out of 5 average rating, 105 reviews

Cute farmhouse in a park like setting on 10 acres

Come relax away from it all, in the middle of it all. Our super cute farm house is located on 10 peaceful acres in Wesley Chapel where you can sit on the covered porches and watch our abundant assortment of wildlife including deer, tortoises, and rabbits ALL while having your coffee or wine. You can see all of the stars in the night sky, yet you are 5 mins from shopping, dining and entertainment and a mere 15 mins from Tampa. 5 mins from I-75. Complete privacy, but centrally located.

Guesthouse in Spring Hill

A screened-in pool area is highlighted by a clear blue sky and scattered clouds. The pool, partially covered, is surrounded by light-colored pool decking. Lush greenery and palm fronds frame the scene, providing a relaxing outdoor space.

J&M Homestead

Relax with the whole family at this peaceful place to stay. Close to I-75 and Suncoast Parkway in Pasco County. Located north of Land O Lakes, Florida, in Pasco Trails, a gated community of acreage and horses. Outlet mall, many eating establishments and sports complexes within half-hour drive. We have had to institute a policy of "no smoking. To be clear, we are retired couple who live in the main house. The apartment is attached but has its own entrance and is self contained.

4.99 out of 5 average rating, 197 reviews

4.99 out of 5 average rating, 356 reviews

The tiny home is set amidst a lush forest backdrop, featuring a welcoming entrance that is framed by large windows. A spacious wooden deck is adorned with comfortable seating, including two bright blue chairs and two red chairs. A black hammock hangs between trees, inviting relaxation.

Campsite in Thonotosassa

The Palm Tree Getaway

Want to reconnect with Nature? Cross it off the bucket list with our ‘Tiny-Home’ style stay near the Hillsborough State Park. Rated #7 on PureWow as one of the 20 Best Airbnb Cabins. This Modern Luxury tiny home was thoughtfully crafted to capture the natural beauty of its old Florida virgin forest surroundings. Glamping at its finest with the best modern conveniences like a full gourmet kitchen, spa like shower, 5G FiberWi-Fi Internet, TV, and a super quiet Mini SplitAC & Heating.

5.0 out of 5 average rating, 213 reviews

The guesthouse is set on a green lawn, surrounded by trees. A friendly horse grazes nearby, accompanied by a variety of free-ranging chickens and ducks. The exterior features a welcoming porch with wooden railings, adding to the farm's relaxed atmosphere.

Farm stay in Zephyrhills

HORSE FARM Retreat, Newer Built Private Guesthouse

Escape to our private guesthouse located in our peaceful but lively 7-acre farm with our family of horses, ponies, Guinea hens, ducks, roosters, chickens, bunnies, cats, & very lovable dogs. Enjoy grabbing fresh eggs, giving animals treats, puppies belly rubs, grilling, making s’mores at the fire pit, and enjoying the farm life! PLEASE read entire listing if little ones will be joining :-) NOTE: Our horses are not available for riding (see our guidebook for great alternate options)

4.87 out of 5 average rating, 102 reviews

A modern kitchen features white cabinetry with a marble countertop. A geometric backsplash adds a contemporary touch. Open wooden shelves hold potted plants, glassware, and decorative items. A variety of baked goods is displayed on a stand, while an electric stove and microwave complete the cooking area.

Villa in Wesley Chapel

Why stay at a hotel when you can stay at a Resort!

Come enjoy this gorgeous Villa, completely renovated into a comfy cozy cottage atmosphere with lots of character. One bedroom with a king bed, it’s own full bath and large screen tv? Short and long terms welcome. Tons of restaurants nearby. A half hour in one direction takes you to Busch Gardens, an hour in the other takes you to Universal Studios, Disney World and Seaworld. The beach is about an hour west or enjoy sitting on the back patio where it is quiet and peaceful!

Tiny home in Wesley Chapel

A tiny house, characterized by its vibrant green exterior and metal roof, is positioned alongside a gently sloping ramp leading to the entrance. Surrounding foliage and gravel pathways offer a natural setting, while the background displays open fields and a fading sunset.

King Lake Hideaway

Experience something different Our Tiny house with the amenities of home. Enjoy our very private spot in nature. Beautiful lake view. This is a tiny house. 280 sq feet including the loft. Lots of natural light. It’s perfect for relaxing. We are close to beaches, Sporting venues, museums the aquarium and Busch Gardens in Tampa. Situated between Epperson and Mirada lagoons. Wesley Chapel has movie theaters, mini golf, shopping and restaurants within a short drive.

4.97 out of 5 average rating, 174 reviews

Guesthouse in Zephyrhills

A spacious living area features a comfortable sectional sofa adorned with decorative pillows. A coffee table sits in front, with a tray positioned on top. The kitchen in the background includes a black refrigerator and a dining table surrounded by chairs, illuminated by pendant lighting.

Under The Oaks Cottage

A charming cottage nestled beneath majestic oak trees, combining country living within reach of city amenities. This comfortable space features one bedroom with a king size bed along with built in bunk beds in the main living area. Savor a morning cup of coffee in the screened back porch while enjoying the beautiful tropical foliage. Chickens, goats, cows, and a horse forage nearby. You could possibly be entertained by the goats playing on the roof-tops.

4.99 out of 5 average rating, 125 reviews

4.88 out of 5 average rating, 156 reviews

Home in Land O' Lakes

Delightful elegant lake home

Escape to a hidden slice of Florida paradise where luxury, tranquility, and breathtaking waterfront views create an unforgettable stay. This stunning lakefront retreat in beautiful Land O’ Lakes offers the perfect balance of upscale comfort and peaceful relaxation. Surrounded by serene bird sanctuary views and glowing Florida sunsets, this private getaway was designed for guests who want more than just a place to stay — they want an experience.

Popular amenities for Wesley Chapel family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.89 out of 5 average rating, 183 reviews

Home in Spring Hill

Ranch Pool Resort with Horses jacuzzi nearby park

4.94 out of 5 average rating, 179 reviews

The exterior of a modern tiny home is framed by vibrant greenery and colorful decor. A red umbrella shades a patio area with two red chairs, while a sliding glass door provides a glimpse into the inviting interior.

Tiny home in Lutz

Tiny Lime House, Cozy Modern Bright Garden Retreat

4.97 out of 5 average rating, 177 reviews

A private outdoor area features a golf putting green with a textured surface, a jacuzzi with soft blue hues, and a wooden pergola. Near the pergola, a grill is provided alongside comfortable seating. Vibrant green walls and string lights enhance the inviting atmosphere.

Guesthouse in Tampa

"Luxury Casita/Jacuzzi/Bush Gardens/USF/Casino"

4.98 out of 5 average rating, 242 reviews

An outdoor porch features a two-person Jacuzzi, inviting relaxation while overlooking a lake. Warm lighting is provided by lanterns, creating an ambient atmosphere against the backdrop of a colorful sunset and silhouettes of trees.

Tiny home in Dade City

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

4.81 out of 5 average rating, 109 reviews

Home in Carrollwood

Pool & Hot Tub | Game Room, Fire Pit, Grill

4.92 out of 5 average rating, 168 reviews

Luxury Retreat~Private Hot tub~9 mins to Downtown

4.79 out of 5 average rating, 156 reviews

Walk to Raymond James Stadium! Pool/ Hot Tub Home!

4.81 out of 5 average rating, 151 reviews

Home in Northdale

Tampa Vacation Home - 3BR 10 PPL - Pool

Family- and pet-friendly home rentals

4.82 out of 5 average rating, 141 reviews

A single-story home features a light beige exterior, complemented by a double garage and a covered entrance. Lush greenery surrounds the front yard, with trees providing shade. The driveway leads to the garage, offering convenient access to the home.

Home in Land O' Lakes

Home away from Home

4.94 out of 5 average rating, 395 reviews

Farm stay in Dade City

Florida Breeze - 18 Acre Wildlife Sanctuary

4.95 out of 5 average rating, 161 reviews

A heated swimming pool is surrounded by a covered patio. A dark wicker seating area is visible next to the pool, along with a grill and an outdoor projector displaying an image on a wall. String lights create a soft illumination around the space.

Home in Northdale

Cozy Tampa Home with Large Heated Pool

5.0 out of 5 average rating, 103 reviews

The living room features a flat-screen TV on a wooden console. A comfortable, tufted sofa and two leather armchairs are arranged around a coffee table. Natural light enters through the blinds of a nearby window, and decorative wall accents add a simple touch.

Apartment in Dade City

Dade City Cozy Little Coop

A spacious orange house is framed by lush green grass and shaded by a large oak tree. Flower beds with colorful plants line the front, while a clean driveway extends alongside the property. The surrounding area is quiet and residential, with simple fencing visible in the background.

4.97 out of 5 average rating, 236 reviews

beautiful lodging 6 minutes from busch garden

4.78 out of 5 average rating, 45 reviews

‼️3BR in Wesley Chapel, Private Pool, Pet Friendly

A spacious living area is highlighted by a grey sectional sofa and a wooden coffee table atop a light area rug. The room features high ceilings and archways, with natural light illuminating the space. A flat-screen TV is mounted on the wall across from the seating area.

4.87 out of 5 average rating, 82 reviews

NEW - Poolside Oasis Heated POOL Home - 2000 SF

Guesthouse in Zephyrhills

My cabin

5.0 out of 5 average rating, 20 reviews

Family-friendly home rentals with a pool

4.88 out of 5 average rating, 139 reviews

Enjoy every moment

A round above-ground pool is surrounded by a gravel space, featuring a sturdy ladder for access. A bright yellow flotation device rests in the clear water, reflecting the sunlight. In the background, modern buildings and trees provide a sense of openness.

4.85 out of 5 average rating, 122 reviews

The day has arrived, enjoy.

4.78 out of 5 average rating, 105 reviews

Sunny Oasis Tampa: Heated Pool & Paradise

A vibrant outdoor oasis features a cozy plunge pool surrounded by sun loungers. A shaded seating area includes a table with four chairs. The space is enhanced by decorative elements, including a pergola with hanging egg chairs, all set against a lush green lawn.

4.98 out of 5 average rating, 129 reviews

Private Cozy Family Retreat, Pool Oasis Near TPA

4.93 out of 5 average rating, 69 reviews

A spacious living area features high ceilings and natural light, with a comfortable seating arrangement that includes a gray sectional and armchairs. A modern coffee table sits at the center, complemented by a decorative lamp and plants. The area seamlessly connects to a dining space with a large table.

Home in Wesley Chapel

Designers Villa @ Saddlebrook

4.95 out of 5 average rating, 41 reviews

A relaxing outdoor space is showcased with a colorful hammock hanging between two pillars. A white chair complements the setting, surrounded by lush greenery and vibrant plants, creating a peaceful retreat. The tiled patio features a unique geometric pattern that enhances the outdoor experience.

Condo in Wesley Chapel

Saddlebrook Resort Modern Hacienda

4.95 out of 5 average rating, 20 reviews

Luxury Airbnb on Wesley Chapel