Family-friendly holiday rentals in Keystone

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, 125 reviews

Cozy Family Retreat, Tampa: Private Pool Oasis

Welcome to Sunshine on the Bay, a charming 2-bed/1-bath villa that blends comfort and style in a quiet area. Located just 3 mins from Citrus Park Mall and 13 mins from airport you'll have easy access to shopping, dining, and top Tampa attractions. Step outside into your own private backyard oasis, complete with a refreshing plunge pool & grill – the perfect spot to unwind after a long day. Enjoy all the essentials, fully equipped kitchen, as well as a 240V outlet for your EV charger. Book today!

FamilyKitchenTV

4.95 out of 5 average rating, 159 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

“No Cleaning Fee, No Chores” Your family will be close to everything when you stay at this centrally-located home. This home is located 5-10 mins from shopping centers, restaurants, gyms, pet and child daycares, community sport courts, local parks and hospitals. 20-30 mins from Bush Gardens, Downtown, ZooTampa, Tampa Airport, Cruise Port, Ben T Davis Beach, Raymond James Stadium, Hard Rock Casino, Hillsborough State Park and more. Only 1hr 30min from Disney, Universal, Sea World, Lego Park

FamilyIndoor spacesBarbecue

Guest suite in Carrollwood

A combined living and sleeping area is shown, featuring a spacious bed with a black and white plaid coverlet. A kitchenette with modern appliances is visible, alongside a small dining space accommodating two stools. A futon, designed for ample seating, is situated to the side.

4.95 out of 5 average rating, 308 reviews

Soothing Breeze

Cozy Private Studio Suite in Carrollwood Tampa | Patio | Fast Wi-Fi | Free Parking Welcome to your comfortable home away from home in beautiful Carrollwood, Tampa! Our private studio suite offers the perfect combination of privacy, convenience, and a relaxing atmosphere. Located in a quiet residential community with easy access to major highways, shopping, restaurants, and Tampa’s most popular attractions, it is an ideal choice for couples, solo travelers, business guests, and small families

KitchenIndoor spacesLocation

4.95 out of 5 average rating, 198 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

KitchenIndoor spacesBackyard

4.98 out of 5 average rating, 98 reviews

Cabin in Odessa

Cozy 1960’s Cabin in Gated Lake Community

Unwind at the Hoover Haven, a cozy cabin, nestled in a gated lake community. Built in 1963, our cabin has a vintage mountain charm. Families have been enjoying our three adjoining lakes and blankets of trees, for generations. We have a community lake with picnic tables, grills, and a private beach. We have a playground, fishing dock, boat ramp, volleyball, and basketball. 14 miles to TPA airport. 31 miles to Clearwater Beach 30 miles to Weeki Springs 3 miles to the Barn at Crescent Lake

KitchenIndoor spacesDecor

5.0 out of 5 average rating, 210 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)

Indoor spacesFamilyPets

4.94 out of 5 average rating, 325 reviews

An inviting exterior showcases a light blue facade complemented by a stone accent wall. The entrance features a covered porch with a simple light fixture and a welcoming door. A small garden with potted plants lines the pathway, enhancing the entryway.

Guest suite in Northdale

Cozy Carrolwood centrally located to all 1/1

Our one bedroom, one bathroom apartment with a clean stocked kitchen is the perfect place for your next vacation! This is a complete space next to the main property with a private entrance , A/C , parking space, TV cable, Internet/WIFI, First AID, closet space and a sharing Dryer and Washer Machine. Towels, beach chairs and cooler for you to borrow! This premium location offers easy access to restaurants, pharmacies, hospitals, grocery stores and is about 11 miles to Busch Gardens.

Indoor spacesFamilyBathroom

4.99 out of 5 average rating, 350 reviews

A spacious cabin is gently illuminated by string lights, creating a warm glow against the evening sky. Surrounding the home are trees and a hammock, with a grassy area leading up to the porch where seating is visible.

Farm stay in Odessa

Farm and lake stay at Maison de L'eau Douce

LAKEHOUSE PRIVATE cabin-farmhouse décor-full kitchen/living room-cozy bedroom/full bath-W/D- 2.5 acres-2 flat screen TVs with Roku (Netflix, Spectrum cable app, and more)-bamboo hard wood flooring- high thread count sheets-very comfy queen bed. IKEA Sleeper sofa in livingroom. Kitchen: gas range-dishwasher-microwave-Keurig machine. Wooded setting-large deck with views of the lake. WIFI. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

FamilyIndoor spacesCondition

4.95 out of 5 average rating, 166 reviews

Apartment in Carrollwood

Sweet Home

🏡 Cozy Vacation Apartment – 1 Bedroom, 2 Beds, Bathroom and Separate Kitchen This beautiful one-bedroom apartment features two beds, a private bathroom, and a fully separate kitchen, ideal for a comfortable and relaxing stay. 🌿 Cozy and serene atmosphere, perfect for disconnecting. ☀️ Ideal for couples, friends, or travelers looking for comfort. 📍 Located in a quiet area, in the center of all Tampa attractions, perfect for enjoying a vacation

Indoor spacesFamilyBathroom

4.92 out of 5 average rating, 118 reviews

A cozy kitchenette is featured with sleek white cabinetry, a compact refrigerator, and a granite countertop. Two seating areas are provided: a striped armchair and three bar stools positioned around a counter. Natural light filters in through a nearby window, illuminating the space.

Farm stay in Odessa

Cabin 1 - Marigold Moments

Discover the peaceful retreat at Cahaba Cabins, a hidden gem nestled on a working microgreen farm in Odessa. The property offers a unique blend of charm and agricultural expertise. We offer three cozy cabins where you can unwind and reconnect with nature while still being close to everything the Tampa Bay area has to offer. Each cabin offers two queen beds, a private bathroom, and a kitchenette—providing all the essentials for a relaxing stay.

FamilyIndoor spacesLayout

4.97 out of 5 average rating, 150 reviews

The living area features a spacious layout with a comfortable gray sofa and a decorative wooden coffee table. A flat-screen TV is mounted on the wall, while a well-equipped kitchen with modern fixtures is visible in the back. Natural light enters through the windows, creating a bright atmosphere.

Home in Carrollwood

Charming House 2B/2B Centrally Located Tampa Bay

Come and enjoy our house, 2Bedroom/2Bathroom with a clean full kitchen is the perfect place for your next vacation! This is an entire 1200sqft, AC, dryer/ washer, huge parking space, Smart TVs, internet/Wi-Fi, First AID and closet spaces. It fits up to 6 adults. This premium location offers small driving distance to restaurants and Super Walmart, is about 3 minutes to Westfield Citrus Park Mall. Busch Gardens (9 miles away).

FamilyIndoor spacesOutdoor spaces

4.85 out of 5 average rating, 189 reviews

A private entrance is visible, featuring a clean white gate that leads into the apartment area. A paved walkway of gray stones is bordered by white gravel and greenery, creating an inviting access point. Nearby structures can be seen, emphasizing the neighborhood's quiet environment.

Apartment in Tampa

Private apartment perfectly located in Citrus park

A comfortable, quiet, and private apartment located in the Citrus Park area. A private entrance to a fully furnished apartment; includes a small kitchen, washer and wifi. The veterans expressway is 1.5 miles away, that can get you anywhere in Tampa within 15 minutes! Citrus Park mall 1.7 miles away. Several eateries, shops, and Tampa trail within a 1 mile radius. Tampa internal airport 12 miles away.

FamilyKitchenBackyard

Popular amenities for Keystone family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A heated pool is enclosed by a screened lanai, featuring a unique shape with a brick border. Lounge seating is present around the pool, while a hammock is visible in the background. The tranquil area is surrounded by high wooden fencing for privacy.

4.91 out of 5 average rating, 236 reviews

Rooms with a Pool

Indoor spacesFamilyParking

4.97 out of 5 average rating, 174 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"

Indoor spacesFamilyView

A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.

4.93 out of 5 average rating, 136 reviews

The Jungalow SOHO - Pool/Hot Tub

Indoor spacesFamilyWalkability

4.95 out of 5 average rating, 385 reviews

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

Indoor spacesKitchenWalkability

Superhost

Home in Carrollwood

4.8 out of 5 average rating, 107 reviews

Tampa Pool Home | Hot Tub, Game Room, Sleeps 10

FamilyIndoor spacesCondition

5.0 out of 5 average rating, 169 reviews

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

Bayside Retreat your tropical oasis

FamilyKitchenBeach

4.98 out of 5 average rating, 239 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)

Indoor spacesKitchenValue

A hot tub is set on a wooden deck surrounded by bar stools, with views of a lush backyard and a serene lake beyond. Tall palm trees frame the scene, while the sky displays soft clouds and warm lighting.

4.95 out of 5 average rating, 344 reviews

The perfect lake house getaway near the airport.

Indoor spacesKitchenCheck-in

Family- and pet-friendly home rentals

Superhost

A screened-in pool area features a private pool surrounded by a tiled deck, with ample space for seating and relaxation. The structure provides sun protection and is situated next to the house, blending outdoor and indoor elements.

4.82 out of 5 average rating, 130 reviews

Entire house in Tampa w/ Heated POOL!

Indoor spacesFamilyCheck-in

4.98 out of 5 average rating, 268 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

Bay Lake Cottage

FamilyKitchenSleep quality

Guest suite in Carrollwood

A cozy sleeping area features a plush queen-sized bed with a patterned throw blanket. A lamp sits on a bedside table, illuminating a nautical-themed artwork above the bed. A comfortable chair is positioned nearby, and a decorative 'Beach' sign adorns the wall.

4.94 out of 5 average rating, 410 reviews

Taste Of Florida-10 mi from Tampa Airport

Indoor spacesKitchenTV

4.93 out of 5 average rating, 129 reviews

A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.

Home in Palm Harbor

Lakefront home near beaches w/ waterview, pets ok

KitchenFamilyLayout

Superhost

A modern living area is furnished with a blue sofa adorned with decorative pillows and a yellow accent chair. A coffee table sits on a patterned rug, and a media console holds decorative items. A wall-mounted television is visible, with soft lighting provided by a ceiling fixture.

4.92 out of 5 average rating, 316 reviews

Tropical Paradise

FamilyKitchenCondition

4.94 out of 5 average rating, 393 reviews

Farm stay in Dade City

Florida Breeze - 18 Acre Wildlife Sanctuary

FamilyKitchenCheck-in

Guesthouse in Town 'n' Country

A well-appointed bedroom features a spacious bed adorned with a seaside-themed quilt. Two comfortable chairs are positioned near a window, allowing natural light to fill the room. A desk and television are also visible, providing functional space for work or relaxation.

4.96 out of 5 average rating, 375 reviews

Luxury Modern Apartment A near Beachs and Airport

FamilyIndoor spacesQuiet

Tiny home in Tarpon Springs

A modern sleeping area is defined by flowing curves and a bright green and white color scheme. Two spacious beds feature plush pillows and decorative accents. Soft lighting highlights the unique wall design and climate control unit, contributing to a fresh and clean ambiance.

4.95 out of 5 average rating, 195 reviews

Luxury Modern Tiny Home

Indoor spacesKitchenBackyard

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 170 reviews

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

Home in Palm Harbor

Coastal Escape: Heated Pool, Playground&Family fun

KitchenIndoor spacesOutdoor spaces

A seating area features a woven bench adorned with tropical-patterned cushions, positioned against a green wall with a neon sign. The inviting pool glimmers in the background, surrounded by a screened enclosure that enhances the outdoor experience.

4.99 out of 5 average rating, 220 reviews

Tropical Getaway, Perfect Home & Great Location

FamilyIndoor spacesDecor

4.99 out of 5 average rating, 105 reviews

A screened-in pool area is highlighted by clear blue water and a unicorn float. Surrounding greenery adds a natural touch, while shaded seating is positioned on the deck. Sunlight filters through the enclosure, creating a bright, inviting space for relaxation and leisure.

Guesthouse in Westchase

Cottage in Paradise.

KitchenFamilySleep quality

4.82 out of 5 average rating, 122 reviews

A vibrant red flower stands in the foreground, drawing attention to the tranquil blue pool beyond. The pool area, enclosed by white fencing, is set against a backdrop of green foliage, complementing the peaceful outdoor setting.

Home in Northdale

¡25% OFF in August! Eco Getaway & Golf-Heated Pool

FamilyKitchenQuiet

4.87 out of 5 average rating, 160 reviews

A spacious outdoor area features a heated private pool surrounded by a screened lanai. Lounge chairs are positioned nearby, and a dining set provides a space for meals. Lush greenery is visible in the background, enhancing the tranquil atmosphere.

Home in Tarpon Springs

Pelican House, Game Room, Pool, 5 min to Beach

KitchenIndoor spacesDecor

4.99 out of 5 average rating, 126 reviews

Villa in Palm Harbor

The Palm Haus • Heated Pool • Near Beach • Games

Indoor spacesFamilyAir conditioning

A heated saltwater pool and spa are presented, set against a serene waterfront view. Lush palm trees and well-maintained landscaping frame the area, while the tranquil canal reflects the clear blue sky. Comfortable seating is positioned nearby for relaxation.

4.96 out of 5 average rating, 171 reviews

NEW Heated Salt Pool & Spa on Waterfront Canal

FamilyIndoor spacesLayout

The kitchen features wooden cabinetry, a central island with seating, and modern appliances. Natural light enters through the glass doors, illuminating the granite countertops. A coffee maker and dishwasher are visible, and the tiled floor adds a polished finish to the overall space.