Family-friendly holiday rentals in Westchase

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, 101 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!

Guest suite in Logan Gate Village

Two bright yellow chairs are positioned on a grassy area, overlooking a serene lake. The tranquil water reflects surrounding greenery and features a decorative flamingo. A peaceful atmosphere is created by the nearby trees and open space.

4.99 out of 5 average rating, 195 reviews

Monterey Suite at Citrus Park

You will enjoy a sparkly clean Studio Suite with a private patio area and a peaceful lake view, comfortable adjustable queen bed, full bathroom, cute kitchen and computer station with high speed internet. Conveniently located ,14 minutes to airport/toll , walking distance to Super Walmart. Minutes to Citrus Park Mall , AMC Theaters , Publix, Costco, Sprouts, Airport, Busch Gardens, Raymond James Stadium, NY Yankees Training Camp, Upper Tampa Bay Trail were you can rent bikes and many more.

Guest suite in Logan Gate Village

The open dining area features a modern table with metal chairs, accented by a checkered tablecloth. Natural light fills the space, illuminating the sleek kitchen in the background. A cozy living room is visible, showcasing comfortable seating arrangements.

4.86 out of 5 average rating, 261 reviews

Entire apartment, close to everything 2B/1B

Our two-bedroom, one-bath 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, dryer/ washer, parking space, TV Cable, internet/WiFi, First AID, dresser and closet space. Towels, beach chairs and cooler for you to borrow!This premium location offers walkability to the restaurants and Super Walmart, and is about 3 minutes to Westfield Citrus Park Mall. Busch Gardens (9 miles away).

4.97 out of 5 average rating, 175 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

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, 119 reviews

Entire house in Tampa w/ Heated POOL!

Our home is a 3/2. You walk into a open space with the dining room, living room & bright kitchen. The 1st bedroom is the Master Bedroom, equipped with a full bathroom, spacious closet, King Size bed & full body mirror. The 2nd bedroom has a queen bed, closet space, decorated with touches of care & is right next to the bathroom. The 3rd bedroom has 2 twin beds, FL touch vibes & is steps away from the bathroom. outside a beautiful backyard with your own private pool! Pool heated at a fee.

4.93 out of 5 average rating, 176 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!

5 out of 5 average rating, 204 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)

4.97 out of 5 average rating, 347 reviews

A spacious sleeping area features a modern white bed dressed in a black coverlet, complemented by matching throw pillows. A sleek dresser stands nearby, and the wall behind the bed showcases a stylish wavy pattern in black and silver. A small seating area with two chairs is visible.

Guesthouse in Tampa

Romantic Getaway*FREE Decor AnyOcassion*Relax Bath

A cozy place to have your vacation in Tampa, private entrance and parking.We include decorations for all occasions:birthday,wedding,special day, show your love, and more! Contact us with your ideas and we'll make this trip unforgettable! Located in a central area of Tampa, close to Bush Garden/Adventure Island, Raymond James Stadium,Tampa International Airport,Ybor City,Downtown Tampa,Clearwater Beach and more! Peaceful and centrally-located place to enjoy as a couple to your liking.

Home in Timberlane Woodlake

A ping pong table is positioned near a sparkling pool, offering a space for leisure and fun. Surrounding the pool, a spacious patio area includes several outdoor chairs and a dining table. Lush green plants provide a natural touch to the fenced backyard.

4.89 out of 5 average rating, 114 reviews

Boho Oasis • Pool •Fire Pit • Near Beach & Airport

Welcome to my 3-bedroom, 2-bath Airbnb home in vibrant Tampa, Florida. BoHo Zen-style oasis, complete with a pool, BBQ area, and ping pong table, provides the perfect backdrop for your getaway. Just 15 minutes from the airport and the Bay Area. centrally located near major stores, convenience is at your doorstep.. Fully equipped kitchen and bedrooms are beautifully decorated, offering comfort and restful nights can't wait to host you and share this peaceful haven with you…☺️

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’

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

Welcome to Tampa Bay! The home is central to everything Tampa Bay and is 1 hour 20 minutes from Orlando. This home includes a three guest rooms, 1.5 bathrooms, a living and a family room, kitchen, dining room, bar, office and a backyard lanai with a large heated pool area. You get the entire home and there is nobody else staying at the same time. It is in a quiet suburban neighborhood, about 40 minutes from downtown Tampa, Clearwater, and St. Petersburg.

Popular amenities for Westchase family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 203 reviews

A fenced outdoor deck features a private spa tub surrounded by tropical landscaping. Comfortable lounge chairs and a shaded seating area create a relaxing space, while the vibrant turquoise cottage provides a cheerful backdrop. The scene is brightened by natural light filtering through the trees.

Cottage in Safety Harbor

Lush Harbor Oasis with Private Hot Tub

4.94 out of 5 average rating, 118 reviews

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.

Home in Palma Ceia

The Jungalow SOHO - Pool/Hot Tub

A foosball table occupies the foreground with a clear view of the private pool shimmering in the sunlight. The surrounding area is enclosed with mesh screens, featuring lush greenery in the background, complementing the inviting water and a beach ball floating on the surface.

4.87 out of 5 average rating, 108 reviews

Ultimate Getaway: w/ Pool, Patio, Pool Table & BBQ

4.91 out of 5 average rating, 153 reviews

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

Home in Palm Harbor

Peaceful Pet friendly 2 BR cottage with hot tub.

4.96 out of 5 average rating, 376 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

4.98 out of 5 average rating, 131 reviews

Home in Largo

[Top Pick] Family Fun Retreat | Heated Pool

4.91 out of 5 average rating, 148 reviews

A private pool area is surrounded by lush greenery, featuring a spacious pool with a spa at one end. Sunlight reflects off the clear water, highlighting the relaxing atmosphere of the outdoor space.

Home in Sunset Park

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

4.99 out of 5 average rating, 264 reviews

A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.

Apartment in Dunedin

Tropical Paradise

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 42 reviews

Apartment in Tampa

Spacious 3BR/2BA w/ Pool + Gym | Near Airport #4

4.99 out of 5 average rating, 363 reviews

A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.

Cottage in Dunedin

Walk to Downtown and Waterfront - Private Yard

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

4.93 out of 5 average rating, 150 reviews

Home in New Port Richey

Luxury Private Pool House ! Mackarosa ! Tampa Bay

4.97 out of 5 average rating, 170 reviews

Home in St. Petersburg

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

4.96 out of 5 average rating, 163 reviews

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.

Home in Tampa Shores

NEW Heated Salt Pool & Spa on Waterfront Canal

Superhost

A simple exterior entrance features a white door with a round window, framed by a small awning. A concrete pathway leads to the door, with a light fixture mounted nearby. The surrounding area is enclosed by a white fence.

Tiny home in Tampa

4.85 out of 5 average rating, 120 reviews

“The Tiny Paradise”

5 out of 5 average rating, 34 reviews

Home in Oldsmar

Modern Private Estate | Central to Tampa & Beaches

Family-friendly home rentals with a pool

A single-family home with a dark exterior is framed by lush greenery and palm trees. A spacious driveway leads to a two-car garage, while a vibrant lawn adds a touch of color. Large windows create a welcoming facade, showcasing the inviting entrance.

4.88 out of 5 average rating, 57 reviews

CasaBella

The outdoor living area features a heated pool surrounded by stone-tiled decking. Lounge chairs are positioned nearby, offering relaxation under a shaded roof. A BBQ grill is visible, complemented by greenery and comfortable seating in the background, creating an inviting space for gatherings.

5 out of 5 average rating, 12 reviews

(HGR) Poolside Paradise: Airbnb Retreat

A well-maintained private pool area is enclosed with a screened lanai, offering protection from insects. The pool's clear water reflects the blue sky with scattered clouds, while the surrounding patio features an outdoor table, creating an inviting space for relaxation and enjoyment.

4.88 out of 5 average rating, 109 reviews

Tampa Getaway Pool Home

4.9 out of 5 average rating, 10 reviews

Welcome to Villa Frankely!

4.93 out of 5 average rating, 145 reviews

A screened-in patio features a heated swimming pool, surrounded by white decking. The pool offers a view of the canal with palm trees and neighboring properties beyond. The tranquil outdoor space is complemented by a backyard with swings and a dock visible in the background.

Home in Tampa Shores

Waterfront Resort with HEATED POOL!

A spacious heated pool is enclosed within a screened area, featuring a gently curved shape. Lounge chairs are arranged nearby, with views of a serene lake visible through the screen. Decorative lights are strung across the ceiling, adding a relaxed ambiance.

5 out of 5 average rating, 44 reviews

Lake House Westchase area. Heated Pool Waterfront!

A serene pool area is framed by lush greenery, with a clear blue pool inviting relaxation. Gentle steps lead into the water, and a wooden deck extends nearby, offering additional seating. The tranquil view of the lake canal enhances the peaceful atmosphere of the space.