Holiday houses in Sand Key

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Top-rated holiday rentals in Sand Key

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
An aerial view showcases a coastal neighborhood along the intracoastal waterway, featuring a single-story home with a gray roof and a landscaped front yard. Palm trees line the driveway, and nearby properties reflect a variety of architectural styles, emphasizing the serene waterfront setting.
Villa in Indian Rocks Beach
5 out of 5 average rating, 53 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

IRB Harbor House, your coastal getaway in the heart of Indian Rocks Beach. This unique shared property concept with semi-private villa boasts 2 cozy bedrooms, 2 modern bathrooms & full size kitchen; perfect for small families, small groups & professionals. Enjoy the convenience of upscale private living with resort style heated pool on a shared property Whether you're here to soak up the sun or simply relax, Harbor House offers the perfect blend of comfort & convenience for your beach vacation!

Guest favourite
Two white Adirondack chairs are placed under a blue umbrella, facing a stunning sunset over the Gulf of Mexico. The foreground includes lush greenery, while the horizon features a vast ocean view with clouds reflecting the warm colors of dusk.
Townhouse in Indian Rocks Beach
4.93 out of 5 average rating, 73 reviews

Beachfront, Amazing Views, 2 Patios, 3 Bdrm w/6 Bd

Experience the ultimate BEACHFRONT escape with breathtaking panoramic ocean views. Featuring 3 bedrooms and 2.5 bathrooms, this coastal retreat comfortably accommodates up to 8 adults plus little ones. A private beach gear closet stocked with essentials makes every beach day effortless. Relax with a drink or meal on the balcony or patio before stepping directly onto the sand. Beautifully maintained and highly rated, this retreat is backed by glowing guest reviews that truly speak for themselves.

Top Guest favourite
Home in Oldsmar
4.98 out of 5 average rating, 45 reviews

Modern Private Estate | Central to Tampa & Beaches

Experience this private 1-acre, modern home designed for space, calm, and everyday comfort. Surrounded by mature oaks and palms, this serene property offers rare privacy just minutes from Tampa Airport, Clearwater Beach, Safety Harbor, St. Pete, and top attractions. Enjoy a chef’s kitchen with modern appliances, spacious living areas, and peaceful outdoor spaces with a patio, electric grill, and koi pond. Ideal for families, longer stays, & guests who value tranquility, and a thoughtful design!

Top Guest favourite
Home in Indian Rocks Beach
4.91 out of 5 average rating, 102 reviews

Waterfront house w/ dock, Walk to Beach, Dogs OK!

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.

Top Guest favourite
Bungalow in Indian Shores
4.96 out of 5 average rating, 197 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

Guest favourite
Apartment in Indian Rocks Beach
4.89 out of 5 average rating, 95 reviews

Hot tub| 5 Min Walk to Indian Rocks Beach| Sleep 6

Walk to the beach in 5 mins 🏖️ + fully renovated luxury retreat Wake up to sunshine, sip coffee just steps from the shore, and unwind in a beautifully designed 2BR/2BA getaway made for relaxation. ✔ Prime location — short walk to the beach ✔ Comfortable, spacious layout perfect for couples or small groups ✔ Designed for a stress-free, feel-at-home stay Whether you’re here for beach days, sunset walks, or a peaceful escape, this is the kind of place guests wish they booked longer.

Top Guest favourite
Home in Largo
5 out of 5 average rating, 19 reviews

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

You asked, we delivered. Inspired by our 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🏝️.

Top Guest favourite
Condo in Indian Shores
5 out of 5 average rating, 7 reviews

Oceanfront Condo · Rooftop Terrace · Arcades

Step onto the private rooftop terrace and the Gulf stretches out in front of you — golden hour, warm breeze, a putting green underfoot, nowhere else you'd rather be. Inside, the kids are deep into NBA Jam while the waves crash just beyond the balcony. Hello Sunshine is a direct oceanfront condo in the heart of Indian Shores — designed like a magazine spread and stocked for the kind of trip people still talk about long after they've unpacked. ☀️

Guest favourite
A private heated pool is framed by comfortable loungers and a vibrant blue sky with scattered clouds. A gentle breeze rustles the palm trees in the background, enhancing the serene atmosphere of the outdoor space.
Home in Indian Rocks Beach
4.86 out of 5 average rating, 36 reviews

Deep Water Dock, Heated Pool, 3 Bedroom House

BTR# 2085 Slice of Paradise is the perfect boater's getaway in beautiful Indian Rocks Beach, Florida on the Gulf of Mexico. The three bedroom, two bath home has a large heated pool, deep water dock that can accommodate larger boats and kayaks and paddle board for local exploration. It's also easily walkable to the beach and local restaurants and bars. The house has newly renovated kitchen and bathrooms and a large private backyard.

Top Guest favourite
A bright living area features a comfortable light-colored sofa and armchairs, complemented by a decorative round coffee table. Large glass doors provide an unobstructed view of the beach and palm trees outside, allowing natural light to fill the space.
Condo in Indian Rocks Beach
4.98 out of 5 average rating, 166 reviews

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...

Top Guest favourite
A modern building with a mix of light-colored stucco and wood paneling is shown. The three-level structure features multiple balconies and large windows. A landscaped front yard includes palm trees, and a driveway accommodates a parked black vehicle.
Home in Indian Rocks Beach
4.95 out of 5 average rating, 42 reviews

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! ☀️ 🏝️

Top Guest favourite
Aerial view of the property highlights a private dock with a kayak, surrounded by lush tropical landscaping. A tiki dining hut is situated on the spacious lawn, providing a serene outdoor space. The waterway can be seen flowing alongside the home, enhancing the natural setting.
Home in Largo
5 out of 5 average rating, 64 reviews

Waterfront with Dock, Heated Pool, Kayaks, Games

Escape to the Magical Manatee Waterfront Cove in Largo, FL! This private retreat for 12 offers stunning water views, a heated pool/hot tub, and a private dock frequented by manatees. Enjoy kayaks, a game lounge, and a chef's kitchen, all just 8 minutes from Indian Rocks Beach. Perfect for families and pet-friendly, this vibrant oasis is your ultimate Florida getaway.

Popular amenities for Sand Key holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Belleair Beach
  6. Sand Key