Kid-friendly vacation rentals in Oldsmar

4.91 out of 5 average rating, 287 reviews

An inviting outdoor seating area is presented, featuring two wicker chairs and a small table. A decorative lamppost stands beside the entrance, which is framed by a stylish door with a rounded window. Lush greenery and a decorative piece are visible in the background.

Guest suite in Tampa

Cachita Studio

Cachita Studio is something to enjoy, both for business or vacations, as a hostess I strive to provide my guest with his best stay, providing details of quick use and always attentive to any questions from my client. I accept suggestions my job is you, always at your service Cachita Studio es algo para disfrutar, tanto para negocios o vacaciones, como anfitriona me esmero en proporcionarle a mi huésped su mejor estadía, proporcionándole detalles de uso rapido y siempre atenta a cualquier duda

Guesthouse in Palm Harbor

A spacious bedroom features a king-size bed with a stylish tufted headboard, draped in golden bedding. Two bedside lamps provide soft illumination. The room is complemented by modern tile flooring with a marble pattern, and a ceiling fan enhances comfort.

4.97 out of 5 average rating, 309 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite attached to Large house located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower. Access to shared pool and patio, backyard and Sundeck. Room includes refrigerator/freezer, Microwave, Coffee maker, Iron and kitchenette. Bistro set in room. Private entrances to room and patio/backyard. No shared space. Cable TV, Streaming and Wi-Fi . Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Guesthouse in Palm Harbor

A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.

4.9 out of 5 average rating, 141 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

4.98 out of 5 average rating, 112 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

The cabin is viewed from the water, featuring a stylish exterior and a spacious deck. A newly constructed dock extends over the calm canal waters, surrounded by lush greenery. A clear blue sky enhances the inviting natural setting.

4.78 out of 5 average rating, 262 reviews

*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin

Experience True Old Florida! Papa’s Cozy, Rustic, Oceanfront Cabin. One of the last true Old Florida neighborhoods in the area. Located near charming Oldsmar. This is a Saltwater Gulf canal, only a few houses down from open the open Gulf in Tampa Bay. Great for the outdoorsy vacationer. Brand new dock. 2 kayaks (individual rider) & 2 bicycles provided. Depth of the canal moves up and down with the tides. It’s usually shallow but has many fish in high tide. Central location to Tampa & beaches!

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.

4.96 out of 5 average rating, 219 reviews

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’

4.89 out of 5 average rating, 288 reviews

A guest suite features a spacious bed with a soft purple comforter. Two nightstands flank the bed, and a tall clock adorns the wall above a small dining table. The modern decor includes a cozy seating area with vibrant accent colors.

Guest suite in Tampa

The Gardens

The Gardens is a private guest suite in Tampa, FL close to everything you need for a perfect vacation. The Gardens is located within 12min from Tampa International Airport. The suite is attached to the home but is completely separate. The Gardens is located in Town & Country, a quiet, safe, and well-kept residential neighborhood. The suite is Self-Check-in, equipped with Smart TV, WIFI, Microwave, Fridge, Keurig Coffee Maker, Hair Dryer, Iron, and Queen Bed.

4.96 out of 5 average rating, 103 reviews

A bright studio features a spacious bed with navy bedding and a light-colored headboard. A kitchenette is visible in the corner, equipped with a refrigerator and microwave. A small desk and chair are positioned nearby. A ceiling fan provides additional comfort.

Guest suite in Tampa

Studio with private entrance and bathroom

A private studio attached to a home. Has its own private entrance. And will feel like you're in hotel room. Located in the heart of Tampa! 15-20 minutes to downtown or the airport, and about 30-45 minutes to Clearwater beach. Also within a 5 mile radius of USF, Busch Gardens, and the Moffit Center. You have 1 free parking space to go along with it in the driveway. Extra fee for Early check in and beach equipment if needed.

4.86 out of 5 average rating, 100 reviews

A spacious living area features light wood flooring and neutral wall colors, complemented by large windows that allow natural light. White furniture, including sofas and a glass coffee table, complements a decorative chair and a nearby entertainment unit.

Home in Oldsmar

Private In-Law Suite with Beautiful Bay View

This is not just a room. It is a beautiful and generous suite with your private living room over looking the old Tampa Bay. In the morning, you can enjoy your coffee while listening to birds singing; in the evening, you can enjoy the sunset on your dinner table. It is minutes from parks, from shopping centers, 15 minutes from beach, and 25 minutes from the airport.

4.96 out of 5 average rating, 297 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.

Vacation rentals for every style

Get the amount of space that is right for you

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Oldsmar kid-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Kid-friendly house rentals

A spacious sleeping area features a dark bedframe with a decorative blue and white patterned comforter. A well-equipped kitchenette is visible, showcasing modern appliances and a stylish bar area with two stools. Natural light illuminates the room, highlighting clean, neutral tones.

4.69 out of 5 average rating, 230 reviews

Tampa Bay Cozy apartment

JoniusRating, 5 stars3 weeks ago

Great place will definitely stay here again and very friendly and peaceful definitely a place I will recommend

4.84 out of 5 average rating, 122 reviews

A private outdoor area is illuminated by soft string lights, featuring a hot tub enclosed by draped curtains for added privacy. The surroundings are designed with a concrete floor, providing a clean and accessible space for relaxation.

Home in Oldsmar

Hot Tub, Heated Pool, 2 Master Suites, Beach

IzaRating, 5 stars1 month ago

This house in Oldsmar Florida was absolutely gorgeous. it was just the vibe we needed for our 22nd anniversary. It was So quiet and peaceful. 25 minutes from Tampa. 25 minutes from the beach. The most delicious sushi around the corner.

5 out of 5 average rating, 12 reviews

A selection of woven storage baskets is displayed on a countertop, featuring neatly arranged napkins and two water bottles. A decorative sign reading 'HOME SWEET HOME' adds a personal touch to the arrangement, blending function with a welcoming aesthetic.

Home in Palm Harbor

Palm Harbor Renovated Hideaway!

CherisseRating, 5 stars2 weeks ago

Great location. A quick 35 min ride into Tampa or St Pete. Great host

4.83 out of 5 average rating, 119 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

DavidRating, 5 stars2 weeks ago

Perfect little studio space for one or two folks. Bed was very comfortable. Microwave and Keurig were convenient We found the instructions to be perfectly clear and helpful.

4.88 out of 5 average rating, 24 reviews

A corner duplex villa is seen with a two-car garage and a welcoming entrance. Mature trees provide shade over the driveway, and a landscaped front yard features greenery along the home’s facade, creating a serene atmosphere.

Home in Palm Harbor

Beachhouse Inspired Villa Close Honeymoon Island

KaitlynRating, 5 stars3 days ago

First off I’d like to say that Sophia and Andrew were exceptional hosts. Unfortunately we got in really late and Sophia was still available to help with our check-in! The place was beautiful and perfect for our stay, clean, tidy, quiet and roomful. We brought our 2 doggies and the fenced in backyard was perfect for them. Very unique to see a piano, and a record player (which we definitely used.) All in all we would 100% stay again and recommend anyone looking in the area to book!

4.86 out of 5 average rating, 22 reviews

Aerial view captures lush greenery surrounding the property, with various trees and plants creating a natural landscape. In the distance, the water of upper Tampa Bay can be seen, complementing the serene setting. The neighborhood features multiple residential homes nestled among the trees.

Home in Oldsmar

Walk to the water from this pet friendly home!

DavidRating, 5 stars1 week ago

beautiful space. surrounded by beautiful nature. quiet. lots of light with the skylights. gorgeous remodeled bathroom. if you need a quiet respite for your trip, this is the spot. thank you!

A narrow outdoor space is lined by white fencing, featuring two black metal chairs with colorful cushions positioned on a gray brick path. Soft lighting is provided by string lights overhead, creating an inviting atmosphere. A small potted plant is situated between the chairs.

4.95 out of 5 average rating, 57 reviews

Beautiful in Tampa

NestorRating, 5 stars3 weeks ago

Excellent stay. For us the location was perfect. The place is nice and clean. The host is very friendly and helpful.

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.

4.98 out of 5 average rating, 246 reviews

Private Studio-2, Exquisite space/King Bed /TAMPA

BrattanyRating, 5 stars3 days ago

Great place to stay. Luciano was very helpful. Everything we needed was close by. Would definitely stay again!

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Kid-friendly apartment rentals

4.99 out of 5 average rating, 177 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!

DianaRating, 5 stars3 days ago

We just spent one night at Ramon’s place. We came out for a weekend for a concert. Wowww what a great find!!! The place was super modern, clean and beautiful. The bed was a Murphy bed, how clever, and very comfortable. The kitchen was beautiful! We used the fridge and the freezer to keep our drinks cool but we didn’t prepare any food. And the bathroom, especially the huge shower, were wonderful. Thank you Ramon for your hospitality. We would definitely be back.

A cozy bedroom features a large bed dressed in a colorful quilt, complemented by matching bedside lamps on wooden nightstands. A mirrored closet reflects the warm orange walls, enhancing the spacious feel. A desk with a chair is positioned nearby, offering a functional workspace.

4.84 out of 5 average rating, 1,165 reviews

Private Apartment near the airport

KarlaRating, 5 stars3 days ago

This was a wonderful apartment and perfect for my sister and I. Everything was clean and felt like home. I love the private entrance and definitely felt safe! It’s conveniently located near 275, the airport, stadium and Tampa hot spots. Communication and instructions were very clear from the start! This is exactly what we were hoping for and couldn’t be happier. We will definitely be back! Thank you Isisley!

A cozy studio features a spacious bed adorned with light bedding and decorative pillows. A small kitchenette is adjacent, with essential appliances and seating for two. A potted plant adds a touch of greenery, while a bathroom is visible in the background.

4.92 out of 5 average rating, 246 reviews

Happy Place

FrankRating, 5 stars2 days ago

Comfortable stay. Peaceful and relaxing. Thank you Anaisa.

A well-appointed bedroom features a spacious bed with crisp white sheets and a contemporary headboard. Nightstands with lamps are positioned on either side, while a large artwork piece hangs above the bed. The room's floor is adorned with elegant marble tiles, enhancing the overall aesthetic.

4.98 out of 5 average rating, 289 reviews

Northdale Apartment

MonicaRating, 5 stars1 week ago

amazing place. a little far from the airport but definitely a great place to stay with all the amenities they offer.

A cozy sleeping area features a spacious bed adorned with a floral patterned blanket. A desk and chair set is positioned nearby, along with a lamp providing soft illumination. A piece of coastal artwork hangs above the bed, enhancing the serene ambiance.

4.93 out of 5 average rating, 118 reviews

Corner Bay Apartment

CobaRating, 5 stars2 weeks ago

Clean, good communication, and overall great stay.

A compact living space is displayed, featuring a spacious bed with patterned bedding. A small dining table with stools and a mini-fridge are visible. Natural light enters through window coverings, enhancing the modern design. Decorative elements include flowers on the table.

4.95 out of 5 average rating, 241 reviews

Azalea Home

InesaRating, 5 stars1 month ago

Yilena was great! Responsive and friendly in communication. The place was perfect for us. We stayed for two nights while at a Music Convention. Super clean and well-organized. Would definitely return!

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.

4.85 out of 5 average rating, 165 reviews

Private apartment perfectly located in Citrus park

KatieRating, 5 stars2 weeks ago

Great place to stay! I have this book marked for our next time in Tampa. It was just what we needed

A cozy bedroom features a wooden bed frame with a floral-patterned comforter, complemented by matching bedside tables. A lamp provides soft lighting beside the bed, while an air conditioning unit is mounted on the wall. A framed artwork adds a decorative touch to the room.

4.89 out of 5 average rating, 269 reviews

Marrero Villa Paradise

TerryRating, 5 stars2 weeks ago

One of my favorite stays in the area. It's peaceful, clean, and dhad everything you will need to have a comfortable stay. They have added certain amenities that make your stay here so great as they continue to be amazing hosts. As long as I can book this location when available I will continue to do so.

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Kid-friendly condo rentals

4.93 out of 5 average rating, 182 reviews

A comfortable living area features a neutral-colored sofa, a round dining table, and a ceiling fan. Large sliding glass doors provide access to a balcony, allowing natural light to fill the space and offering views of palm trees outside.

Condo in Tampa

Waterfront Condo - Sunset View of Tampa Bay

LarryRating, 5 stars1 week ago

Chris‘s Airbnb was excellent. He was a great host and the view was everything we had hoped for. It was a very comfortable condo with a nice bed and the amenities which included the pool bar made it very fun also. It was a great location and we would definitely go back.

4.9 out of 5 average rating, 203 reviews

A resort-style pool is situated within a gated community, featuring clear blue water and a gently curving shape. Surrounding the pool are lounge chairs, a shaded seating area, and lush landscaping with palm trees, enhancing the tranquil setting.

Condo in Clearwater

Very cozy quality condo close to Clearwater Beach

KarenRating, 5 stars3 weeks ago

The condo was wonderful - spacious, spotless and super quiet which made for a relaxing stay. I liked having a washer and dryer, dishwasher and beach supplies. Marta was a thoughtful and responsive host who checked in on me during my stay, which I appreciated.

4.82 out of 5 average rating, 196 reviews

A serene waterfront area features wooden decking alongside dark water, surrounded by lush palm trees and greenery. A small bench is situated on the deck, providing a peaceful spot to relax and enjoy the tranquil lake views.

Condo in Palm Harbor

Lakeside 2- Bed Apartment Near Clearwater Beaches

BobbieRating, 5 stars5 days ago

Beautiful condo. Comfortable beds. Great restaurants near by. Beautiful beaches near by. The swimming pool was clean and the kids really enjoyed it. Would definitely stay again.

4.75 out of 5 average rating, 241 reviews

A wooden pier extends over smooth waters, bordered by rocky outcrops. The sky is painted in vibrant hues of orange and purple as the sun sets on the horizon, casting a tranquil glow across the scene.

Condo in Tampa

Rocky Point paradise

GlendaRating, 5 stars2 days ago

It was a very clean place and a great location. We were there to attend an event at Raymond James which was only a short drive, and close enough to the beach to enjoy that as well. The balcony was nice and private. We loved being able to just sit and enjoy the peaceful water view!

4.95 out of 5 average rating, 301 reviews

A serene balcony view captures a sunset over calm waters, with silhouetted palm trees in the distance. A small round table with a lantern sits next to a comfortable chair, creating an inviting space for relaxation.

Condo in Tampa

Modern Waterfront Condo - Captivating Sunset Views

KateRating, 5 stars2 days ago

Rosana was an excellent host- very responsive, kind, and accommodating. Fun location on the bay with a great view, pool with towel service, and bar/grill with great burgers. Fire pit on the little beach at night with great view of sunset. The unit is in a quiet location within the complex with a view of the beach and bay. The trade-off is that the unit is a bit far from the elevator (though close to stairs). Great experience overall.

4.97 out of 5 average rating, 125 reviews

A spacious living area features a comfortable beige couch and a plush armchair. Natural light fills the space through large glass sliding doors leading to a balcony overlooking greenery. A wall-mounted TV and a small dining table with stools are also present, enhancing the welcoming environment.

Condo in Palm Harbor

Newly Remodeled Condo In The Heart Of Innisbrook

PatrickRating, 5 stars2 weeks ago

Our stay at Alan's place was absolutely fantastic! Alan was incredibly responsive and helpful. The condo was perfect for our weekend golf tournament. We had a wonderful time and would definitely recommend this place to others!

4.84 out of 5 average rating, 129 reviews

A living area is shown featuring a dark blue sectional sofa, accompanied by a wooden coffee table. Natural light enters through a window adorned with sheer curtains. A floor lamp provides additional light beside the sofa, while wall art adds a touch of color.

Condo in Dunedin

Charming Condo next to Honeymoon Island

WendyRating, 5 stars1 month ago

My friends and I had a fabulous getaway. Spent the first day on Honeymoon Island, ventured to nearby Dunedin and Tarpon Springs the other day dues to weather. But we enjoyed our stay very much and would definitely return!