Family-friendly holiday rentals in Oldsmar

A modern seating area is depicted with a sleek black sofa adorned with a colorful throw and decorative pillows. A small table holds a vase of flowers. Through the door, a balcony area can be seen, framed by light curtains and greenery visible outside.

4.97 out of 5 average rating, 652 reviews

Davenport Dream Suite

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. Small computer table. 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, 240 reviews

"Chic/cozy Petite Studio •"Spa-Inspired Shower. 1”

Welcome to your serene hideaway in Citrus Park, where modern comfort meets thoughtful design. Just 11 minutes from Tampa International Airport, and free parking on premises this stylish and private studio is the perfect spot for couples, solo travelers, or business guests seeking a peaceful and rejuvenating stay. Located in a quiet, safe, and central neighborhood, you’ll enjoy a private entrance, free on-site parking, and easy access to restaurants, grocery stores, and major Tampa attractions.

4.99 out of 5 average rating, 145 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

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, 388 reviews

Taste Of Florida-10 mi from Tampa Airport

Welcome to our Taste of Florida! This wonderful, private little Coastal gem (nestled in Beautiful Carrollwood and only 10 miles from the airport) is perfectly located and equipped for vacationers, business travelers and those who just want to get away from the hustle and bustle. Whether you are visiting any of the nearby premier hospitals, theme parks, outlet malls or college campuses, this private in-law suite studio is sure to allow you to relax during your stay in the Tampa Bay Area.

4.99 out of 5 average rating, 209 reviews

The modern kitchenette features sleek cabinetry, a stainless-steel refrigerator, and a countertop with three black bar stools. A flat-screen television is positioned nearby, and natural light is observed reflecting off the tiled floor, enhancing the open layout.

Apartment in Clearwater

Welcome to your cozy studio!

This charming furnished studio apartment is the perfect blend of comfort and convenience, offering everything you need for a delightful living experience: *Fully Furnished *Comfortable Sleeping Area *Equipped Kitchenette *On-Site Laundry Room *Private Parking Space *Private Patio Prime Location: Conveniently located close to shops, restaurants, parks and just 10 minutes away from the breathtaking Clearwater Beach

A modern sleeping area features a queen bed dressed in teal bedding. A sleek, illuminated headboard and a large mirror are displayed above the bed. The room is complemented by a bedside lamp and a stylish wardrobe, enhancing the overall ambiance.

4.86 out of 5 average rating, 230 reviews

Washington

This stylish and brand new place to stay is perfect to guests that want to getaway to a romantic and peaceful environment and at the same time very friendly place for couples that come with children looking for safety and confortable stay. This suite has all that you need, a queen bed, separate kitchen very useful with coffee machine and a beautiful and modern bathroom. The outdoor is very spacious and airy.

4.84 out of 5 average rating, 175 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.

4.85 out of 5 average rating, 134 reviews

A work area is positioned near a window, featuring a sleek desk and an adjustable white chair. Light gray curtains frame the window, allowing for natural light. A small lamp and decorative item are placed on the desk, contributing to the space's functional design.

Home in Tampa

My Little White Space .

My apartment is located an excellent position of access to different places of Tampa bay .Apartment with independent entrance.Near to: Tampa international airport-4miles Mall international plaza-4 miles Downtown Tampa 8.7 miles Raymond James stadium Beaches within 5 miles. NO CHILDREN OR PETS WILL BE ADMITTED.

4.96 out of 5 average rating, 303 reviews

The charming cottage features a bright yellow front door, flanked by potted plants. A welcoming porch is screened with white framing. The well-maintained yard is adorned with manicured grass and a path leading to the entrance, with a white picket fence visible in the background.

Cottage in Oldsmar

Louisa's Cottage

This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmar’s main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants .This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.

4.86 out of 5 average rating, 195 reviews

A modern bedroom features a spacious bed with patterned bedding. A flat-screen television is mounted on the wall opposite the bed. A small desk and chair occupy a corner, while a door leads to a bathroom area. Light-colored walls enhance the bright, airy feel.

Apartment in Tampa

Lovely 1-bedroom rental 10 min from TPA

Enjoy easy access to everything from this perfectly located home base. We are just 10 mins away from the airport. Our home is located in a quite neighborhood where you can relax and rest. This place was recently renovated so you will be enjoying modern luxury.

4.98 out of 5 average rating, 265 reviews

A spacious bed is centered in the room, embellished with a patterned bedspread. Nightstands with lamps are positioned on either side. A ceiling fan is visible overhead, and a large piece of wall art adds a touch of character. A bathroom can be glimpsed through an open door.

Home in Tampa

Private Studio-2 Exquisite space/King Bed/Near TPA

Enjoy your stay in Tampa in this cozy, newly remodeled studio! This studio is located at the center of Town and Country and is a short drive from Tampa International Airport (7 miles, which is 14 minutes away from the studio).

4.86 out of 5 average rating, 126 reviews

A cozy guesthouse space features a spacious bed against a vibrant green wall. A sitting area is furnished with a neutral-toned couch and a small table. A kitchenette with wooden cabinetry includes a microwave and a small fridge, enhancing functionality.

Guesthouse in Tampa

Small but Spacious! Private guesthouse

Cozy 1 Bedroom guesthouse with private entrance! Comes with a kitchenette area with microwave and sink. Small fridge to store your food as well!

Popular amenities for Oldsmar family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 195 reviews

A spacious outdoor deck is shown, featuring a hot tub covered with a protective lid. Blue and white lounge chairs, along with bright cushions, are arranged for relaxation. The cottage's vibrant turquoise exterior is complemented by a cheerful yellow door and lush surrounding greenery.

Cottage in Safety Harbor

Harbor Oasis | Hot Tub | Private | Lush Backyard

4.85 out of 5 average rating, 136 reviews

A studio apartment includes a spacious bed with a light blanket, complemented by a cozy sofa and a festive Christmas tree. Soft lighting creates a warm atmosphere, while large glass doors provide access to natural light. A dresser and TV add functionality to the space.

Home in Holiday

Comfort In Holiday

Apartment in Pinellas Park

A charming terrace features a jacuzzi surrounded by wooden walls adorned with greenery. Soft lighting illuminates the space, creating a cozy atmosphere. Two turquoise chairs and a small blue table invite relaxation and conversation.

4.82 out of 5 average rating, 191 reviews

Oasis Terrace

4.92 out of 5 average rating, 224 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 Tampa

Rooms with a Pool

4.85 out of 5 average rating, 489 reviews

A spacious balcony offers water views featuring palm trees and lounge furniture. The exterior of the building showcases a light-colored facade. A living area is furnished with a soft couch and a dining set, bathed in natural light from large windows. A pool area is visible with lounge chairs and palm trees lining the water's edge.

Condo in St. Petersburg

Waterfront condo on top floor @ Boca Ciega Resort

Guesthouse in St. Petersburg

4.97 out of 5 average rating, 190 reviews

Centrally Located Cozy 1-bed Private Cottage!

4.96 out of 5 average rating, 150 reviews

The kitchen area features a sleek layout with modern appliances, including a blue vintage refrigerator. A spacious sink is integrated into the countertop with ample storage cabinets above. A cozy seating area is located to the left, showcasing a daybed with decorative pillows.

Campervan/RV in Tampa

Cozy Camper + outdoor shower, fire pit & hottub!

4.94 out of 5 average rating, 173 reviews

A hot tub is positioned beside a fire pit, surrounded by greenery and decorative lighting. A projector screen displays images, creating an inviting atmosphere for outdoor entertainment. The space is enhanced by potted plants and gravel pathways, offering a serene retreat.

Guesthouse in Tampa

HOT TUB & Free Wine !, Ping-Pong, Outdoor Theatre

Family- and pet-friendly home rentals

A bright studio space features a full-size bed with gray linens and decorative pillows. A mounted television is visible, alongside a sleek kitchenette with a microwave and granite countertops. Bar stools provide seating near the large window, which overlooks a lush outdoor area.

4.94 out of 5 average rating, 267 reviews

Modern and Comfortable One Bedroom Studio

4.98 out of 5 average rating, 188 reviews

A spacious backyard is highlighted by a hammock suspended between two trees, inviting relaxation. A black dog and a tan dog can be seen exploring the grassy area, surrounded by tall trees adorned with Spanish moss. A guesthouse is visible in the background.

Farm stay in Odessa

Farm and lake stay at Malfini Cay

A light-colored room features a spacious bed with a patterned white coverlet, positioned against a modern headboard. A small desk and chair are included, alongside a wall-mounted television. A closet with louvered doors and framed artwork enhance the minimalist decor.

4.89 out of 5 average rating, 122 reviews

Villa cashita, private accommodation,

4.79 out of 5 average rating, 159 reviews

Home in Tarpon Springs

Mins to Beach/Studio Home/walk to dwtn/FreeParking

4.89 out of 5 average rating, 401 reviews

A spacious bedroom features a large bed adorned with a patterned blue and white bedspread. Soft lighting from a bedside lamp provides a warm ambiance. A ceiling fan and two windows with sheer curtains contribute to the bright atmosphere, while a decorative piece hangs on the wall.

Apartment in Clearwater

Comfy Guesthouse # 1 - 4 miles to Clearwater Beach

4.94 out of 5 average rating, 125 reviews

An outdoor area features a heated pool surrounded by a screened enclosure, providing a bright and airy setting. Comfortable lounge chairs are positioned nearby, with greenery visible outside the enclosure. Natural light filters through the screens, creating a serene space for relaxation.

Home in Palm Harbor

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

4.85 out of 5 average rating, 101 reviews

The outdoor space features a heated pool surrounded by a smooth concrete deck. Several lounge chairs are positioned nearby for relaxation. Lush landscaping includes palm trees, and soft lighting adds ambiance to the area, creating an inviting environment for leisure.

Home in Oldsmar

Modern & Spacious Retreat with Private Pool!

4.86 out of 5 average rating, 406 reviews

The exterior of the guest house is framed by lush greenery and palm plants. A patio area is visible, featuring an umbrella and white chairs. A grill is positioned beside the entrance. Natural light streams in through large sliding doors, leading to the yard.

Guesthouse in Odessa

Private Guest House

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 132 reviews

Condo in Clearwater

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

4.9 out of 5 average rating, 124 reviews

The outdoor area features a heated pool with crystal-clear water, surrounded by a screened lanai. Comfortable lounge chairs are placed nearby, providing ideal spots for relaxation. Tropical plants enhance the space, framing a serene environment perfect for swimming and sunbathing.

Home in Palm Harbor

Heated Pool, 10 min to Beach, Close to Restaurants

4.99 out of 5 average rating, 257 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-All Essentials Provided

4.96 out of 5 average rating, 190 reviews

An outdoor tiki hut porch is illuminated by soft string lights. Comfortable seating creates a cozy gathering area, surrounded by lush greenery. A wooden dining table sits in the center, offering a relaxed space for meals or conversation.

Guesthouse in Dunedin

Tiki Hut Cottage

4.91 out of 5 average rating, 322 reviews

A bright studio space features a cozy seating area with a soft blue love seat and a spacious bed adorned with white linens. Natural light filters through sheer curtains, illuminating the wood furnishings and decorative accents throughout the room.

Guest suite in Largo

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

4.89 out of 5 average rating, 120 reviews

A rectangular heated pool is surrounded by a screened enclosure, featuring inviting blue water and colorful inflatable pool toys. Lounge chairs are positioned along the edge, with a light brown paver patio enhancing the outdoor space. Lush greenery is visible in the background.

Home in Clearwater

Family Fun! Heated Pool/Arcade/Foosball + 2 Kings

Guest suite in Tarpon Springs

A heated saltwater pool is surrounded by lush tropical landscaping, with clear blue water reflecting the sky above. A colorful float rests on the water's surface. The screened enclosure provides a barrier while allowing for views of the serene outdoor space.

4.96 out of 5 average rating, 134 reviews

Private pool suite in heart of Tarpon Springs!