Family-friendly vacation rentals in Oldsmar

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Top-rated family-friendly rentals in Oldsmar

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Largo

4.99 out of 5 average rating, 300 reviews

Paradise Cottage Largo 2 miles to beach private+

We are PARADISE COTTAGE and the standards of super host are status quo! Come on down - we're ready for you! Although only 2 miles from the Gulf, we're on high ground! We are on a Priority One Energy Grid. With over 300 plants, many trees, we live in a lush tropical "Paradise". Our guests' highest praises include the private, quiet, serene, safe and secluded attributes we're fortunate to claim, no neighbors while being so close to so much. Read on in the next section "The Space" to learn more

Jul 24 – 31

G$29,229 GYD per night

Guest favorite

Home in Dunedin

4.93 out of 5 average rating, 119 reviews

Everything you'll need, plus! Park Model RV

A relaxing and open space great for beach lovers, cyclists, and people who love the outdoors. This cozy setting provides all the necessities for daily living, plus more to make for a great get away! Accommodates up to four. Within 2 miles of Honeymoon Island State Park and Caladesi Island. Easy drive to Clearwater Beach, St. Pete's Airport and surrounding areas. Short walks to town, bike trails and beautiful Gulf coast sunsets make this a perfect getaway or home base for exploring the area.

Sep 26 – Oct 3

G$18,495 GYD per night

Guest favorite

Apartment in Clearwater

4.95 out of 5 average rating, 186 reviews

Your own apartment, private with patio & driveway.

This Triplex apartment is centrally located in Clearwater near US Hwy 19 and Gulf to Bay Blvd (Rt 60). Clearwater Beach is a straight drive ahead (about 4 miles). This is a large 1 bedroom apartment that is perfect for two, but can also sleep four with the sleeper-sofa. There is a full sized, fully stocked kitchen, and a screened in patio in the back where smoking is allowed. There is a queen bed in the bedroom, and a sleeper sofa in the living room. Free wifi with Ruku streaming TV.

Sep 6 – 13

G$18,280 GYD per night

Guest favorite

Apartment in Treasure Island

4.92 out of 5 average rating, 162 reviews

Treasure Island Beach Apartment #1

Location! Situated on Gulf Blvd, directly across from the 123rd Street beach access in Treasure Island. Walk to John's Pass for restaurants, shopping, bars and music, boat trips and fishing. Two bedroom, one bath private apartment, with all the amenities you need for a great beach vacation - beach chairs, umbrella, cooler, barbecue, bicycles. Master bedroom has queen bed, and Roku tv. Smaller bedroom has twin trundle bed, perfect for the kids. Full kitchen. Off street parking for one car.

Apr 14 – 21

G$26,547 GYD per night

Guest favorite

Condo in Indian Rocks Beach

4.79 out of 5 average rating, 225 reviews

Waterfront Condo w/ Boat dock, 2 min walk to beach

This cozy one bedroom, one bath condo is only 2 blocks from the beach with family-friendly activities, nightlife, and public transportation nearby. The place is perfect for solo travelers, couples, & even small families who looking to have a relaxing time. Located right on the intercostal waterway. You can enjoy your coffee on the dock while watching the sunrise. Also, a great spot for seeing dolphins. Shops, food , and entertainment are all located within walking distance. BTR #266

Sep 13 – 20

G$24,663 GYD per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Dec 14 – 21

G$27,374 GYD per night

Guest favorite

Home in Tarpon Springs

4.93 out of 5 average rating, 103 reviews

Our Gemini Place: Comfort & Charm in Old Tarpon

Welcome to Gemini Place, a cool, quiet 2/2 filled with an easy charm. This solid 1,100- sq. ft house is in the heart of old Tarpon and is a perfect, simple escape for a few days, a few weeks or longer. The north-facing house sits on a one-way brick street and is an easy walk to everything in this quaint, Greek-flavored town. We are close to some of the best beaches in the U.S. We're pet friendly but do have restrictions and a fee that is determined by several factors. Please inquire.

Jul 19 – 26

G$27,047 GYD per night

Guest favorite

Farm stay in Odessa

4.99 out of 5 average rating, 288 reviews

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).

Sep 20 – 27

G$30,823 GYD per night

Guest favorite

Home in Tampa

4.93 out of 5 average rating, 167 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.

Aug 3 – 10

G$29,994 GYD per night

Guest favorite

Home in Clearwater

4.95 out of 5 average rating, 326 reviews

Coastal Cottage 1318 - Bikes and Beach items!

This guest house has been fully remodeled with brand new mini split-air conditioners. Sorry no animals/pets. It shares a parking lot, grill, and laundry with other units. Included with this unit are 5 beach cruiser bikes, bike trailer, 8 beach chairs, 6 beach towels, two umbrellas, one large cooler, one medium size cooler, 2 mesh beach bags, frisbee, football, volleyball, bag of sand toys, beach cart, boogie boards and more! All the extras make it fun!

Jan 27 – Feb 3

G$30,124 GYD per night

Guest favorite

Apartment in Dunedin

4.99 out of 5 average rating, 202 reviews

Tropical Paradise

Watch this video first to experience this wonderful Property https://vimeo.com/444390022 I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 4- (2 adults and 2 children or 4 adults)

Nov 28 – Dec 5

G$39,081 GYD per night

Guest favorite

Bungalow in Dunedin

4.89 out of 5 average rating, 184 reviews

Cozy Park Model RV with Sun Room. No pets

A relaxing space great for beach lovers, cyclist , and people who love the outdoors. Close to beaches restaurants and historic Downtown Dunedin. Located in the Dunedin RV Resort . Honeymoon Island State Park is 3 miles, Clearwater Beach is about 9 miles. Jolly Trolley goes to Clearwater Beach St Petersburg , Tarpon Springs where the sponge docks are. Greek Food and pastries are amazing in Tarpon Springs. NO PETS

Aug 17 – 24

G$18,177 GYD per night