Holiday rentals with a pool in Sand Key

Belleair Beach Oasis w/ Heated Pool - 3mi to Beach

Welcome to BELLEAIR BEACH OASIS! This luxuriously updated 2BR/1BA POOL HOME is minutes away from beaches and golf courses! Walking distance to Belleair grocery, coffee shops, restaurants and more. Enjoy the private and fully fenced resort-style outdoor living featuring: inground pool, modern pergola w/lounge chairs, grill, covered dining and relaxing hammock! You’ll love this quiet Belleair Bluffs neighborhood offering easy commute to St. Pete Clearwater and Tampa Airports, local hospitals, etc.

Steps 2 beach! Beachy and Luxurious! Easy Living!

Easy Living is a beachy newly renovated condo with 2 bedrooms & 2 full bathrooms, nestled between the intercoastal water and the magnificent Clearwater beach! Located a very short walk to the beach (less than 2 blocks) and across the street from a park. The Clearwater Beach Rec Pool is another short two minute walk from the condo! The condominium is quiet area yet, it is within walking distance to practically everything in town, including the beach, many restaurants, bars, Pier 60, & the marina!

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.

"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.

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!

Endless Summer No Hurricane Damage

Endless Summer is the house for exactly that! Endless fun, endless joy, endless family memories……. I recently just finished this gem to be everything a beach house should be. Light, fresh, fun, and located walking distance to the beach. Plus all the little beachy items you need. A beach cart, beach chairs, toys to play with. Did I mention a private pool? Yep for only you and your guests. Heated to 80 degrees to enjoy on days that it’s a bit chilly to hop in the Ocean. BTR # 2122

Triplex across from the beach, heated pool, bikes

☀ Easy access to the beach; just walk across the street! ☀ Stylish shared pool with sunshelf and chaise loungers ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior ☀ 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

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.

Very cozy quality place close to Clearwater Beach

Modern and very cozy one-bedroom condo, clean, quiet, and comfortable. Convenient big kitchen space and bathroom. King bed in master. Sleeping sofa in the living room. All appliances, kitchen pots, and all you need to make yourself home. TV in the living room and Master. Full cable. Fast WiFi. Roku. Beach towels, umbrella, chairs, cooler. 10 min from Clearwater Beach. 20 min from the airport. I put a lot of <3 INTO! You will feel at home in my place!

Seasalt Breeze, by the pool, 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. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

Literally: 15 steps to the Pool, GroundFloor Condo

Unwind at this stunning Complex at Clearwater that resemble a vacation resort, gated community, extremely safe. Don't want to go out? There is everything you need right in the complex: Free Parking, 24/7 Free Gym, steps to the heated Pool with BBQ area and other wonderful-friendly guests for company (if needed), shops and few dining places in walking distance, your private patio to sit, drink, chat and relax; take some time for you!

Downtown Dunedin B&B - Rustic Cabin Studio with He

Welcome to our brand new rustic cabin located in our backyard within walking distance to downtown Dunedin! Everything in the cabin is brand new, fresh & clean! Located in Downtown Dunedin & within easy walking distance to restaurants, breweries, shopping & everything Dunedin has to offer! Dunedin Stadium, home of Spring Training for the Toronto Blue Jays is just 1 mile away...easily walkable!