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, 129 reviews

Private Cozy Family Retreat, Pool Oasis Near TPA

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!

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.

4.95 out of 5 average rating, 161 reviews

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

4.96 out of 5 average rating, 133 reviews

A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.

Home in Odessa

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

4.83 out of 5 average rating, 226 reviews

Spacious home / 35 Foot Pool/Patio on park

Great 4 bedroom 2.5 bath,. 35 foot pool home with covered patio backed up to a beautiful park!! 2 story home.(stairs) Close to airport, amusement parks, restaurants, downtown, stadium and shopping. Parking in driveway. (3 to 4 cars max.) Please know pool is not heated. Also we do not accept pets. No parties or large gatherings are allowed . No motorcycles, campers, RVs or boats allowed. Only 2- 4 night stays. 4-5 day guests only. Garage NOT for use. Thank you for respecting our rules & home!

4.99 out of 5 average rating, 159 reviews

The exterior of a newly constructed barn loft apartment is shown, featuring a wraparound deck accessed by wooden stairs. Beneath the deck, picnic tables and seating areas are visible among the surrounding greenery and trees. The property is set in a spacious outdoor environment.

Barn in Odessa

Cypress Lakes Barn Retreat

Rest & relax at this newly constructed barn loft apartment, located on a 4 acre hobby farm in Odessa, Florida on a private lake. This one bedroom, one bath and kitchen is clean, fun, and convenient. We have 2 daily feedings of farm animals at which you can participate including horses, cows, goats, & chickens; or you can choose to kayak on the lake. This memorable place is anything but ordinary, and is conveniently located 11 miles from the airport and is a quick drive to dining & shopping.

4.81 out of 5 average rating, 120 reviews

A modern open-concept living area features a sleek kitchen with granite countertops and stainless steel appliances. The space is well-lit by recessed lighting and natural light streaming through the windows. Comfortable seating arrangements are visible, along with a fireplace that adds a cozy touch.

Home in Carrollwood

Family-friendly getaway home in the heart of Tampa

Modern home in the heart of Tampa. Within great distance from amazing entertainment, restaurants, cafes, bars, breweries, and much more. Perfect for weekend getaway, business trip, staycation, work-from-home alternative, or cozy home base while exploring everything Tampa has to offer. Step inside to find a bright and spacious living room with tile floors and plenty of natural light. The modern kitchen boasts granite countertops, stainless steel appliances, and everything you need to cook.

4.96 out of 5 average rating, 118 reviews

A well-equipped kitchenette features a granite countertop with three bar stools. Natural light enters through a window, illuminating the space, which is complemented by a small dining area and a comfortable seating arrangement. A wall-mounted TV and a lamp add to the cozy ambiance.

Farm stay in Odessa

Cabin 3 - Nasturtium Nest

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. We look forward to seeing you on the Farm!

4.94 out of 5 average rating, 327 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.

4.99 out of 5 average rating, 352 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).

4.91 out of 5 average rating, 140 reviews

The bedroom features a queen bed with dual pillows and a daybed next to it. A flat-screen television is mounted on the wall. The wood laminate flooring complements the light-colored walls, while a remote control air conditioning unit is positioned above the bed.

Guest suite in Tampa

Private guest suite, up to 4 adults, self check-in

Self-check in NON-SMOKING, NO PETS guest studio with its entrance, private bathroom and kitchen, very fast WIFI, washer and dryer available. Located in a safe area in Tampa Bay. It can fit up to 4 adults. Your own parking space for up to 2 cars. We live on the premises but you will have your own private space with a small yard. The entire exterior of the property is under video surveillance 24/7. DRUG-FREE. ADDITIONAL FEE WILL APPLY IF SMOKING IS DETECTED IN THE SUITE.

4.93 out of 5 average rating, 171 reviews

Flat 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

4.81 out of 5 average rating, 109 reviews

Home in Carrollwood

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

"Every evening ended with us unwinding in the jacuzzi under the stars." That's what a guest had to say about our Tampa home. Days belong to the pool, kids on floats while the grill runs for dinner, and evenings move to the game room and jetted hot tub. Sleeps 10 across four bedrooms: king, two queens, and a full-over-full bunk with trundle, plus a sofa bed. Zoo Tampa 6 miles, Busch Gardens 7, Publix and restaurants minutes away.

Popular amenities for Keystone family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.81 out of 5 average rating, 151 reviews

Tampa Vacation Home - 3BR 10 PPL - Pool

4.91 out of 5 average rating, 236 reviews

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.

Home in Town 'n' Country

Rooms with a Pool

4.96 out of 5 average rating, 202 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

4.9 out of 5 average rating, 164 reviews

Tiny home in Tampa

Luxury 3-Bedroom Tiny House-Sleeps Six People!

4.87 out of 5 average rating, 141 reviews

Stunning South Tampa 6 Bedroom House

4.86 out of 5 average rating, 120 reviews

Golf • Hot Tub • Pool • Fire Pit • Putting Green

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.

Guest house in Tampa

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

4.89 out of 5 average rating, 183 reviews

Home in Spring Hill

Ranch Pool Resort with Horses jacuzzi nearby park

Family- and pet-friendly home rentals

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, 131 reviews

Entire house in Tampa w/ Heated POOL!

4.99 out of 5 average rating, 100 reviews

A heated salt-water pool is enclosed by a screened patio, providing a spacious area for relaxation. Comfortable lounge chairs are positioned nearby, with bright outdoor decor enhancing the inviting setting. Large glass doors open to the interior, allowing natural light to fill the space.

Home in Port Richey

Angelita's Lake Home 3br3ba w/heated pool

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.

Taste Of Florida-10 mi from Tampa Airport

4.94 out of 5 average rating, 411 reviews

5.0 out of 5 average rating, 100 reviews

A screened-in heated pool area is highlighted, featuring a clear blue pool surrounded by a spacious deck. Comfortable seating is arranged nearby, and floating toys add a playful touch. The enclosure provides a bright and airy feel with natural light streaming in.

Home in New Port Richey

Relaxing Beach-Theme Pool Home!

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

4.93 out of 5 average rating, 131 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

4.96 out of 5 average rating, 109 reviews

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

Home in Holiday

Paradise!Renovated waterfront pool home.Sunsets!

4.9 out of 5 average rating, 59 reviews

A scenic outdoor space features a circular fire pit surrounded by several wooden Adirondack chairs. Lush greenery and tall trees frame the view of the tranquil lake, while a canoe rests on the shore nearby.

Home in Odessa

Lakefront Cabin Retreat: Hot Tub, Kayak & PingPong

Family-friendly home rentals with a pool

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.

4.82 out of 5 average rating, 123 reviews

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

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, 222 reviews

Tropical Getaway, Perfect Home & Great Location

4.99 out of 5 average rating, 106 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.

Guest house in Westchase

Cottage in Paradise.

5.0 out of 5 average rating, 172 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

4.99 out of 5 average rating, 128 reviews

Villa in Palm Harbor

The Palm Haus • Heated Pool • Near Beach • Games

4.88 out of 5 average rating, 156 reviews

Home in Land O' Lakes

Delightful elegant lake home

4.88 out of 5 average rating, 219 reviews

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.

Home in Town 'n' Country

Entire residential home, Tampa. 3/2, Pool.