Family-friendly vacation 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.

4.97 out of 5 average rating, 100 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!

4.98 out of 5 average rating, 174 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

4.99 out of 5 average rating, 143 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.

4.93 out of 5 average rating, 175 reviews

A cozy sleeping area features a wooden bed frame with a patterned quilt in soft hues. Two bedside lamps illuminate the space, complementing a floral artwork displayed above the headboard. A ceiling fan provides ventilation in the warm-toned room, accented by neutral walls.

Apartment in Tampa

Stunning Studio in Citrus Park

My beautiful studio apartment is nestled in the heart of Citrus Park/ Carrollwood area. We are walking distance from shops and restaurant. This cozy and spacious studio has a fully equipped kitchen (Keurig coffee maker and complementary coffee, toaster, pots and pans and utensils). The full bathroom has a stand up shower (shampoo, conditioner, and body wash provided). The studio has a private entrance and self check-in for your convenience. **** One parking space available per reservation*

4.96 out of 5 average rating, 110 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!

4.98 out of 5 average rating, 255 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

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

5 out of 5 average rating, 203 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)

4.99 out of 5 average rating, 341 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).

Guesthouse in Logan Gate Village

A cozy bedroom features a spacious bed with plush pillows, illuminated by soft blue lighting from the headboard. A bedside lamp provides additional light, while artwork adorns the wall above the bed. Ample closet space is visible next to the door.

4.98 out of 5 average rating, 112 reviews

Charming Guest House in Tampa

Welcome to your cozy getaway in Tampa! Our guest house combines comfort and style, perfect for any traveler—whether visiting for leisure or work. Relax in a thoughtfully designed space featuring a peaceful bedroom, modern bathroom, and private patio ideal for morning coffee or unwinding in the evening. Nestled in a quiet neighborhood, you’re just minutes away from Tampa’s top attractions, dining spots, and beaches. Book your stay and let us make your visit truly memorable!

4.96 out of 5 average rating, 289 reviews

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.

Guest suite in Tampa

Soothing Breeze

This is a private studio suit located at Carrollwood community. Easy access to Supermarket, Veterans Express Way. There is a fridge, microwave, coffee maker. TV with Roku , Netflix and spectrum channels with wireless internet.There is a queen size bed, individual futon, full bathroom, small dinning room. Nearby Places: TPA Airport 12 miles, 15 ‘ Raymond James Stadium 11 miles 18’ Citrus Park Mall 1.9 miles, 6 ‘ Busch Garden 11 miles, 33 ‘ Adventure Island 11 miles, 28’

4.96 out of 5 average rating, 120 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 beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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.

4.97 out of 5 average rating, 135 reviews

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).

Popular amenities for Keystone family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Bungalow in Ybor City Historic District

A spacious living area features a light brown sofa and wooden accents throughout. Colorful wall decorations and plants create a vibrant atmosphere. A dining table is positioned nearby, and an open kitchen is visible in the background. Light streams in from large windows adorned with blue curtains.

4.99 out of 5 average rating, 383 reviews

Cozy AF Jungle-House Hideaway

4.97 out of 5 average rating, 155 reviews

Home in Largo

[Top Pick] Family Fun Getaway | Heated Pool

4.9 out of 5 average rating, 210 reviews

A bright red bedroom features a spacious bed covered with white linens and decorative pillows. A modern lamp stands on a circular side table, casting warm light. A zebra-patterned rug lies on the floor, adding a bold contrast to the vibrant walls.

Tiny home in Lutz

Tiny Red - Art House & Garden Retreat

4.91 out of 5 average rating, 141 reviews

A private hot tub is situated within a wooden gazebo, surrounded by large glass windows. Light reflects off the water's surface, creating a serene environment. An indoor seating area is visible in the background, enhancing the relaxation space.

Loft in Tampa

Lovely 2-bedroom private Apt. with 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, 229 reviews

Rooms with a Pool

4.98 out of 5 average rating, 129 reviews

Home in Largo

[Top Pick] Family Fun Retreat | Heated Pool

4.98 out of 5 average rating, 209 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)

4.85 out of 5 average rating, 140 reviews

Tampa Vacation Home - 3BR 10 PPL - Pool

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 190 reviews

Home in Palm Harbor

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

Apartment in Land O' Lakes

A private pool area is featured, enclosed by a screened structure that allows for natural light. The serene water is illuminated by sunlight, while the surrounding space is finished with a smooth surface. A comfortable seating area is seen in the distance, accompanied by nearby decorative landscaping.

4.91 out of 5 average rating, 137 reviews

Studio with Pool

4.99 out of 5 average rating, 273 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool/Coffee Bar/Fully Stocked

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, 148 reviews

Cozy Tampa Home with Large Heated Pool

4.95 out of 5 average rating, 144 reviews

An outdoor screened area features a private heated pool surrounded by a spacious deck. Two lounge chairs are positioned nearby, with a barbecue grill present for outdoor cooking. A dining set with multiple chairs is also visible under a covered patio, providing shade and comfort.

Home in Spring Hill

Weeki Wachee Springs heated pool home retreat

A bright living area features a plush, mustard-colored sofa adorned with colorful cushions. In the background, a modern kitchen is visible, equipped with stainless steel appliances and white cabinetry. Pendant lights hang above the kitchen island, enhancing the open-concept layout.

4.95 out of 5 average rating, 150 reviews

3/2, 3 miles to Busch Gar *Pool, Game,CoffeeBar*

4.9 out of 5 average rating, 130 reviews

A spacious living area features neutral-toned walls and two comfortable leather couches, one light and one darker. A glass coffee table sits in the center, accompanied by side tables with lamps. Large sliding doors allow natural light and provide access to an outdoor space.

Home in Oldsmar

Coastal themed home near beach and airport

4.96 out of 5 average rating, 123 reviews

A spacious outdoor area features comfortable lounge chairs and a patio, surrounded by greenery. The deck extends toward the water, with a view of the canal. A covered seating area and plants add to the inviting atmosphere, while overcast skies hint at a serene ambiance.

Cottage in Lutz

Serene Waterfront Cottage with Tranquil Setting

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 130 reviews

A screened-in pool area features a clear, inviting pool with a waterfall and soft blue water. Surrounding greenery provides privacy, while lounge chairs are positioned near the water. Sunlight filters through the mesh enclosure, creating a bright and airy atmosphere.

Home in Spring Hill

Spring Hill, Florida Quaint Paradise

A tranquil outdoor pool area is highlighted, surrounded by lush greenery and palm trees. The pool's clear blue water reflects the sky, which features vibrant hues of pink and purple at sunset. Comfortable lounge chairs are positioned poolside for relaxation.

4.9 out of 5 average rating, 80 reviews

Tropical Haven: Private Pool, Hot Tub, and Bliss

4.83 out of 5 average rating, 66 reviews

A charming cottage is set amidst lush greenery, featuring a covered entrance with a decorative arch. The exterior is painted in a clean white, complemented by dark trim. A window and air conditioning unit are visible, surrounded by well-maintained landscaping.

Guesthouse in Keystone

Adorable Lakefront pool cottage

4.93 out of 5 average rating, 30 reviews

A screened-in balcony area is visible, showcasing views of a large pond surrounded by lush greenery. Bright blue skies and scattered clouds reflect a serene atmosphere. Two striped chairs are positioned for relaxation, set against the tiled floor surrounded by wooden railings.

Condo in Oldsmar

Guest Favorite Waterview- 2 bed/2 bath apt w/pool

4.95 out of 5 average rating, 151 reviews

Home in Dunedin

Dunedin 5 STAR+ Heated Pool+Near Beach

4.89 out of 5 average rating, 55 reviews

A stylish living area is presented, featuring two light-colored sofas adorned with decorative cushions. A central coffee table sits atop a plush area rug. A television is mounted on the wall above a sleek, modern fireplace. Shelving units display decorative items and books.

Home in Odessa

Luxury 5Bedroom 3bath Oasis w/Pool, land. 7beds

4.99 out of 5 average rating, 159 reviews

A heated pool is surrounded by lush palm trees, providing a sense of seclusion. A stone statue and decorative elements are featured along the pool's edge. Sunlight reflects off the water, creating a serene atmosphere in this private outdoor oasis.

Home in Palm Harbor

Tropical Oasis Retreat w/ 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.