Holiday rentals in Sand Key

Oceanview - Steps away from the beach

Welcome to Cozy Corner at Sea Haven. Beautiful, completely renovated, condo with Gulf views from all rooms in a private 6 unit condo complex. Spacious, open floor plan, with 2 master suites, is fully equipped to be your home away from home. Enjoy stunning sunsets and beach views from your 2 private balconies or walk less than 100 steps to the breathtaking beach of Indian Rocks. 2 bedrooms, 2 bathrooms, beds for 5 guests plus a pack-n-play makes it so even the tiniest guest can enjoy their stay.

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.

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

The Marquise 204 is a Beautiful 1300sq ft DIRECT beachfront unit! Direct Gulf front views! Top floor corner unit. Small and quiet 10-unit building. Tremendous location for getaways with family and friends. After arriving you can literally leave your car behind and walk to over 10 local restaurants, bars and shops! Enjoy some of the best sunsets you will see in all of Florida from your private balcony! NO PETS. Renter MUST be at least 25 years old. NOTE: TWO flights of stairs NO elevator.

Charming Beach Bungalow w/ Hot Tub & Pet-Friendly

Cozy Coastal Haven! Fall in love with this charming 1BR/1BA retreat just steps from Indian Rocks Beach’s white sands and stunning sunsets. Perfect for couples or a small family of four, this pet-friendly gem features a private backyard with a bubbling hot tub, beverage chillers, cozy outdoor seating, grill, and beach gear for effortless adventures. Whether you're sipping wine under the stars or strolling to the shore, this dreamy escape is your ticket to laid-back luxury. BTR# 2440

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.

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.

Oceanfront View, Spacious Townhouse, Heated Pool

🌊 This 2BR, 2BA beach home offers breathtaking water views from every bedroom, each with its own TV. The 1st floor features a spacious living room with large TV, full kitchen, and bath, while the 2nd floor hosts both bedrooms and another bath. Relax on the balcony, enjoy the heated pool, BBQ grill, or sun loungers. With beach essentials, elevator access, and stunning views, it’s perfect for your coastal getaway. 🚤☀️

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

The Sunshine House!

Brand new construction! Stunning house with sunlight in every room. Bring the whole family to stay, only a 5 minute walk to the public beach on the Gulf! Also views of the intercostal on the 2nd and 3rd floors. See dolphins from your bedroom! 🐬 Amazing patios with outdoor kitchen, have a dip in the cocktail pool while cool off in the evening. You are going to love this house! ☀️ 🏝️