Holiday rentals in Sand Key

Special Rates! Waterfront,Beach Walk,Dog Friendly!

Rare high-season opening! Wake up to serene water views & start your day w/coffee on your PRIVATE dock. Beautifully renovated waterfront home offers a peaceful escape just steps from Indian Rocks Beach. Enjoy a bright sunroom, stylish interiors, and an easy 2 min walk to the sand. Enjoy full access to Brown Park across the street with playground, tennis & basketball courts. Walk to beach, shops, & restaurants. Perfect for families, groups seeking relaxation or adventure on Florida’s Gulf Coast.

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach

Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!

Heated Pool! Steps 2 beach! Luxurious King bed

Everything is brand new in this completely renovated vacation rental. Located less than a block to the beach and across the street from a park. Enjoy the views of the pool & park from the unit or the private balcony. A luxurious $3,000+ King Puffy Royal Hybrid Mattress provided in the master bedroom will ensure you are sleeping well! Out back is a large HEATED pool, lounge chairs, dining tables, grill, fire pit and more. We provide all your beach needs, towels, umbrella, beach chairs, and more!

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

Modern Coastal Hideaway –Patio & Hammock by Beach!

Sandy Toes Cottage is a fully renovated beach home just 2 minutes from Indian Rocks Beach. Enjoy modern furnishings, a bright kitchen, spa-style bath, free Wi-Fi, and a backyard with fire pit and hammock. Walk to local dining and shops—your perfect coastal getaway. **NEW AIRBNB PRICING UPDATE** Starting mid-October 2025, Airbnb will show all-in pricing—including an increase fee of 15.5% Airbnb service fee (charged directly by Airbnb to me the host), cleaning fees, and pet fees if applicable!

Barefoot Parrot /Walk DT & Waterfront/Private Yard

Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches such as Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly home with designer decor and abundant outdoor space. Walk, bike, or cart to gorgeous sunsets, shops, dining, breweries, and Pinellas Trail. Great for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to an unforgettable stay.

Villa Al GolfoTre WaterfrontOasis openings Apr&May

Pristine villa in the lovely seaside gulf town of Indian Rocks Beach, 2 short blocks to the beach with intracoastal waters in the backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio and your own show stopping indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam beds & security safe.

Beach Across the St | No Stairs |Parking in Front!

Just 150 feet from the beach, this renovated 1 bedroom, 1 bath condo is the perfect coastal escape. Simply walk across the street to the beach, or explore several restaurants just a short stroll away. Enjoy parking directly in front of the unit and easy ground level access with no stairs. Inside, you’ll find a comfortable, welcoming space to relax after a day in the sun. Ideal for couples or solo travellers looking for convenience, comfort and an unbeatable beach location.

Ocean View | Heated Pool | 3 Bed | Island Paradise

Your Private Oasis Awaits at Island Paradise! A haven of comfort and style in our meticulously curated Airbnb accommodations. Modern amenities and local charm, where each space tells a unique story. Whether you seek a cozy retreat, a vibrant urban escape, or a scenic getaway, our listings cater to every taste. Experience the warmth of hospitality and the joy of discovery as you make memories in homes that feel like your own. 6 person golf cart is available for your use!

2/2 condo one block from beach & golf cart, kayaks

BTR# 2463 🌴 This fully renovated 2-bedroom, 2-bathroom condo is just one block from the sparkling sands of Indian Rocks Beach ✨ **Highlights** - 🛋️ Stylish interiors with modern furnishings and beachy vibes - 🛏️ Two cozy bedrooms + two sleek bathrooms - 🍽️ Fully equipped kitchen - 🌅 Private balcony to sip morning coffee 🚗 **Golf Cart Included! ** Cruise around like a local in 4-seat golf cart 🛺💨 - 🛶 Complimentary Kayaks – Paddle out into the Gulf

Luxury Poolside Paradise

Enjoy a spotless 3 bedroom, 1 bathroom home just 5 minutes from Indian Rocks Beach. The home features a beautiful yard with a private heated in-ground pool, perfect for soaking up the Florida sunshine. With two parking spots, a clean and modern interior, and a convenient location close to grocery stores, shops, and restaurants, this home offers the ideal mix of comfort and convenience for your Gulf Coast getaway. Easy access to Clearwater, St. Pete and Dunedin.

Golf Cart, 2 bed 2 Bath, Heated Pool

The Chunky Mermaid is new with tasteful decorations to pull the space together. Big 75" TV, big double queen guest room, and king sized master bedroom. The Chunky Mermaid is the perfect beach house to get your toes in the water in minutes, the perfect beach community to walk to local cuisine, with the perfect creature comforts of home. The space is built for families/groups that want to have fun together with epic sunsets perfect for sun downers.