Family-friendly holiday rentals in Sand Key

Relaxing Coastal Getaway w/ Jacuzzi & Private Yard

Short-Term Rental Studio Near the Beach — Relax, Unwind & Enjoy Privacy Escape to our cozy studio designed for vacations with friends, romantic getaways, or even a productive business trip — all just 3 miles from the beautiful Gulf beaches. Step outside into your private backyard oasis, featuring both sunny and shaded seating so you can lounge however you like. Enjoy a peaceful garden setting, a comfortable outdoor dining area, and a BBQ grill perfect for laid-back evenings at home. Inside, y

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

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Vintage Florida Beach Efficiency

Just a short walk to the beach, this a great beach getaway for couples or families with one child. On your way stop at the Cooky Coconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2024, this unit is updated, very clean & worry free. This cottage is located in a quiet residential neighborhood and a great place to relax. Laundry on shared screened porch. Dogs allowed ($35 extra) add them on # of guests page . Easy refund policy. Level 2 EV charger

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

Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

The Zen Den Studio

Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

Cozy Largo Studio

Fantastic studio consisting of a comfortable queen bed, and small kitchenette, perfect for a long term stay or weekend get away. Parking on premises. Unit was newly renovated and is impeccably kept. Minutes away from popular Indian Rocks beach / Belleair beach and clear water beach. Easy hassle free check in. (This is a one room studio with 1 queen bed as shown) this is a private apartment with its own front door. Not a shared space. Close to the Largo hospital, medical students welcome

Hidden Oasis #3, *construction discount!*

*Construction discount! The yards and upstairs apartment are undergoing renovations. Please note the seating on the decks is limited and there may be noise in this unit during the day from the work above.* Walk into this welcoming apartment and find your paradise! This cozy space has shared access to a large courtyard w/ grill & smoker. Short 10-minute drive to the best free parking along the Gulf beaches (Indian Rocks Beach). Free bikes! Come make yourself at home in this Hidden Oasis 🌴

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.

1925 beach house just steps to the beach. . All shops and resturaunts just a few blocks walk. Beach is 120 steps away. Part of Clearwater Cottages, a group of historic beach houses. This is an entire small house that will sleep 4 Restored antique kitchen. Just cute as a button. Families with pets welcome shared commercial hot tub in recreation area. has queen size bed in private master bedroom and pull out sofa bed in living room . as well as an additional twin bed in the living room

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

Cozy 2 Bedroom - 12 Minutes from Clearwater Beach

Make your vacation relaxing, fun and easy! - Kick back in the hammock or have some coffee with loved ones in the peaceful private backyard. - Take the 12 minute drive to the beach with the provided boogie boards, chairs and sand toys. - Take a walk or bike ride on the gorgeous Pinellas Trail. You'll also find some of the best coffee, food and ice cream on the way. -Golf courses close by. This is a separate unit that shares a driveway and parking area with the front house.

Triplex- walk to beach, heated pool, bikes

☀ Easy access to the beach; just walk across the street! ☀ Stylish shared heated pool with sun shelf and chaise loungers ☀ Fire pit with relaxing swivel lounge chairs, bikes ☀ Beach wagons, zero gravity chairs, cooler, ice, umbrellas, towels, speakers ☀ 3 hole glow in the dark putt putt ☀ Amazon Dots with Unlimited Amazon Music ☀ Fenced-in courtyard w/ outdoor seating, umbrellas, and BBQ grills ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior

Cozy Stylish Home w/ Heated Pool & Big Parking

Welcome to Your Cozy & Stylish Home with Heated Pool + Big Parking! Our newly renovated house combines modern style and cozy comfort with rare amenities you’ll love – a heated private pool and a large parking area for up to 8 cars or even an RV. Perfect for a family trip, a friends’ getaway, a work retreat, or just a relaxing stop on your road adventure – this home is designed to make every stay easy and enjoyable!