Holiday rentals in Sand Key

Organic & Modern~90° Heated Salt Pool~Walk 2 beach

Welcome to our Peaceful Sanctuary! A fully organic coastal retreat in Indian Rocks Beach, just a short walk to the Gulf. Enjoy an organic Avocado King mattress, natural bunk beds, organic linens, whole-home water filtration, 5-stage reverse osmosis drinking water, ceramic cookware, heated pool, tropical outdoor shower, fresh herbs, beach gear, pickleball, and board games — designed for wellness-minded families seeking a restorative beach escape. The beautiful beach is a short 5-7 minute walk!

Barefoot Parrot /Walk DT & Waterfront/Sleeps 8

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

“Sandcastles, Sunsets and Palms”

This 2 bed, 2 bath condo at Crescent Beach Club is located on beautiful Sand Key Island off the western coast of central Florida. It’s unique architecture features two crescent shaped buildings that stand out from the rest. Resort-like peaceful, tranquil and relaxed environment with 24 hour security. Oceanfront pool, private beach access, dry and wet saunas, indoor and outdoor jacuzzis, work out room, tennis courts, billiard room and library. Free WiFi. Food and shopping in walking distance.

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

Walk to Indian Rocks Beach | Hot Tub | 2BR Condo

Escape to our peaceful 2BR/2BA beach retreat in Indian Rocks Beach—just a 5-minute stroll to the sand! This charming, pet-friendly home sleeps 6 and features modern furnishings, a private patio, relaxing hot tub, and all the essentials for a perfect beach day. Ideal for families, couples, or friends, you’ll enjoy easy access to local dining, shopping, and water sports. Unwind indoors with fast WiFi and smart TVs, or soak up the Florida sunshine outside—your perfect coastal escape awaits.

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach

You asked, we delivered. Inspired by our Top 1% listing and consistent 5⭐ stays at “The Tiny Oasis”, Haus De Noir is a moody, boutique 3BR/3BA retreat with Plunge Pool, Hot Tub, Sauna, Outdoor Cinema and More! Slip into the Midnight Kafana, your own after-hours Hideaway Bar with Karaoke, Lights, and Late-Night energy. Fully stocked with everything you need and then some! Family-Owned and Managed! We don’t just host we LOVE what we do! Just 10 mins to Indian Rocks & Madeira Beach🏝️.

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.

3 Bedroom Waterfront Paradise Sleeps 8

Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach on the intercostal! The 3 floors of custom interior decoration and high end furnishings await you. Located on Clearwater Bay with an easy stroll (5-10 min) to Clearwater Beach, Beach Walk, Pier 60, restaurants, and shopping. You are centrally located to everything in Clearwater with luxury accommodations ! !! You have a 2 car garage, community pool, hot tub, grill steps from your back door.

On Private Beach! Full Kitchen Ground Level Unit 7

Fully remodeled in 2025! We’re back & better than ever! ON Private Beach 1 bd/1ba with breathtaking Gulf views! This 1 bedroom unit w patio leading to private beach features a full kitchen & 1 king bedroom + pullout sofa sleeping 4 guests. Smart TVs, we furnish linens, towels, toiletries, beach chairs/towels & gas grill. 1 free parking space included. For additional availability see IDENTICAL unit same location Tide Vibes #7 and 2 bedroom unit #5, sleeps 6.

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

Luxury Beach Bungalow | Walk to Dining & Sunset

Welcome to Mango! Nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits! 🥭

CBC 1-17G – Amazing Gulf & Intercoastal Views!

CBC 1-17G Luxurious Condo with Stunning 360-degree Waterfront Views ⛵Experience unparalleled coastal luxury in this magnificent 2-bedroom, 2.5-bath condo perched on the 17th floor of the Crescent Beach Club. With a sprawling 2,005 square feet, this end unit offers five balconies with breathtaking million-dollar views of the Gulf of America and the Intracoastal Waterway. ✨ 5% Off Weekly/ 10% Off Monthly Stays💲 ​​​​​​​