Holiday rentals with outdoor seating in Sand Key

2 BR/2 BA Key West Retreat, A+Pool, 3m 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.

Cozy coastal grandmother condo, walk to the beach!

Bright, stylish and quaint. Newly remodeled and furnished to make you feel like you're at your own beach home. Grab your provided beach chair and towel for your short jaunt down to the beach(a football field away) and take a deep breath; let the endless views, waves crashing and sand between your toes take you away. The well appointed kitchen can be used to simply make coffee or a full dinner. Don't feel like cooking? No problem! Indian Rocks Beach offers local coffee, lunch and dinner spots!

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #MangoIRB, 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 of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, #MangoIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Walk to Downtown and Waterfront - Private Yard

Curated coastal décor and a private yard with grill, all walkable to town define this modern Dunedin retreat. Your oasis- yet you'll be just steps from Main Street’s dining, shops, & live music. Walk to waterfront sunsets or drive to the powder-white sands of Honeymoon Island & Clearwater Beach. Sleeps 6: spacious 2 bedroom; 2 kings and 2 twin spots on sleeper couch. Fully loaded with kids and beach gear. Barefoot Parrot Cottages—where contemporary design meets effortless coastal living.

Your private Waterfront Pool home!

Fully permitted rebuilding after Helene is complete. Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

An original early 1900 Indian Rocks Beach bungalow, beautiful and bright with pool! Across Gulf Boulevard from 8th Ave beach access with all the comforts of home. Rest in the tropical garden pool, hang out in the private tiki hut out back , hop on the trolley to explore the area. Many shops and restaurants are within walking distance. Splash Harbour water park at the Holiday Inn is walking distance for a day of fun! Have an unforgettable stay! City tax#1479

Cozy Retreat, private unit, NO PETS

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Walk-in distance to Publix grocery store and nearby restaurants. Location is central with short distance to nearby beaches, attractions and other nearby towns. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport and Disney World This location is loved by “snowbirds”

2 King Suites | Stunning Views | Walk Everywhere!

Escape to Dock of the Bay! ✅ Two KING suites + sofa bed ✅ 5-minute walk to beach ✅ Stunning waterfront views ✅ Full kitchen ✅ Heated pool & sun deck ✅ Beach gear & wagon ✅ Free parking! 👨‍👩‍👧 Traveling with a group? We also own the condo next door -- “Dock Holiday” (www.airbnb.com/h/dockholiday-clearwaterbeach). Tell your friends or book both together—Dockside Duo (www.airbnb.com/h/docksideduo). Double the space and double the fun!

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...

𖤓Updated Stilt home: just steps to the beach!𖤓

Experience a stylish and relaxing beach vacation at our vacation retreat! We are a very popular spot for Honeymooners and anniversaries! As a 4-year Superhost, we offer a charmingly renovated home just steps away from the beach and local restaurants. Explore Indian Rocks Beach with our provided bikes and unwind in the bubbly spa. Escape the everyday and find paradise here! BTR #2292

Home away from home!

This 1 bedroom guest house in Clearwater, is truly a fantastic retreat. Feel at home with all the amenities. Great location, safe surroundings, fenced private courtyard for smoking, 5 miles from Clearwater beach. Affordable, queen bed, kitchen, shower, Netflix, free driveway parking on premise. Thoroughly cleaned after every guest check out. Come and enjoy in this beautiful city.

Indian Rocks Beach 2BR I Walk to Ocean + Cafes

☀️ Your beach escape awaits—just a 5-min stroll from the sugar sand shores of Indian Rocks Beach! Enjoy a private 2BR home with no shared spaces, a fenced yard for sunset hangs, and everything you need for a seamless coastal stay—beach gear, bikes, eScooters & a 6-seater golf cart. Walk to restaurants, parks & shops—NO CAR NEEDED! Business Tax Receipt No. 1529.