Holiday rentals in Sand Key, Clearwater

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Top-rated holiday rentals in Sand Key, Clearwater

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

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Guest favourite

Flat in Indian Rocks Beach

4.98 out of 5 average rating, 120 reviews

Heated Pool! Fully remodeled! Steps 2 beach!

LOCATION! LOCATION! LOCATION! Completely renovated vacation rental located less than 1 block to the beautiful beach and across the street from Brown Park. This unit is located on the second floor of a small two story building with four total units. Out back is a large HEATED pool, lounge chairs, a dining table, grill and more. Walk out of the unit down a beautiful palm tree lined path to enter paradise! We provide you w/ all your beach needs, towels, umbrella, beach chairs, floats and much more!

Top guest favourite

Guest house in Largo

4.99 out of 5 average rating, 332 reviews

Paradise Cottage Largo Beaches 1 mile safe private

We are PARADISE COTTAGE, and the standards of super host are status quo! We're ready for you! Although only 2 miles from the Gulf, we're on high ground! We are on a Priority One Energy Grid. With over 300 huge potted plants, many trees, etc we live in a lush tropical "Paradise". Our guests' highest praises include private, quiet, serene, safe and secluded; attributes we're fortunate to claim We have no neighbors while being so close to so much. Read the next section "The Space" to learn more.

Top guest favourite

Cottage in Indian Rocks Beach

4.99 out of 5 average rating, 175 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #CocoPalmsIRB, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem that radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore. The Gulf of Mexico beckons just two blocks away, offering pristine fluffy sands and unforgettable sunsets. As the sister cottage of Mango, #CocoPalmsIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits!

Superhost

Hotel room in Dunedin

4.73 out of 5 average rating, 226 reviews

Seaside Artisan *Dog Friendly* 5

This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s. There is no lobby for the guests, however we do list for rent the owner suit with front desk on airbnb as well. You can find it under “Seaside Artisan Motel Owner Suit”. This Airbnb is walking distance from the restaurants, shops and bars in Dunedin. It’s about 4 miles away from Honeymoon Island and about 6 miles from Clearwater Beach.

Guest favourite

Flat in Dunedin

4.95 out of 5 average rating, 210 reviews

The Coastal Retreat

Studio apartment. Light airy Coastal Eclectic décor. Walk in closet, full size bath, Fully equipped kitchen . Key west style tropical courtyard with fish pond. Off street parking . Gas grill and outdoor dining area. One block off the Pinellas Bike trail, walking/biking to historic downtown Dunedin, Toronto Blue Jays spring training. Minutes to the 3 of the country's best beaches! Clearwater Beach, Honeymoon Island, and Caladesi Island.

Top guest favourite

Cottage in Dunedin

4.97 out of 5 average rating, 308 reviews

Walk Downtown and Waterfront Barefoot Parrot 3

Experience coastal modern luxury in this stylish, spacious upstairs 2-bedroom cottage. Steps from Main Street Dunedin. Walk to restaurants, shops, and breweries or take a short stroll to stunning waterfront sunsets. A quick drive to Honeymoon Island and Clearwater Beach, this pet-friendly retreat boasts two king beds, a sleeper sectional, and serene treetop views. Your sunny, unforgettable coastal escape awaits—book your getaway today!

Superhost

Guest suite in Largo

4.83 out of 5 average rating, 264 reviews

Cozy Largo Studio

Great studio consisting of a comfortable queen bed, and small kitchenette, perfect for a long term stay or weekend get away. Parking on premises. Unit was newly renovated and is impeccably kept. This is a one room studio, minutes away from popular Indian Rocks beach / Belleair beach and clear water beach. Easy hassle free check in. (This is a one room studio with 1 queen bed as shown) Medical students welcome!

Guest favourite

Apartment in Indian Rocks Beach

4.97 out of 5 average rating, 129 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...

Guest favourite

Flat in Belleair Beach

5 out of 5 average rating, 14 reviews

NEW Beachfront Oasis with Pool in Belleair Beach

BEACH ACCESS a few steps away from your front door! Views of the beach included with an in-ground pool and picnic area on one of the most beautiful beaches on Florida's Gulf Coast! Our fully renovated apartment is fully equipped with a combo kitchenette, dining space, living room with smart tv, and bedroom with smart tv. If you're looking for a peaceful and fun beach getaway, you've come to the right place!

Top guest favourite

Guest suite in Largo

5 out of 5 average rating, 193 reviews

Cozy Private Bedroom Suite Private Entry King Bed

Spacious private master bedroom suite with private entrance and driveway! King bed. Private spacious bathroom! Fridge, microwave, Keurig coffee maker. Located in a large home. No access to the rest of house. 5 miles to Indian Rocks Beach. 8 miles to Clearwater. 2.5 miles to Botanical Gardens and Heritage Village, both FREE! 30 minutes from Tampa airport and 20 minutes from Clearwater St Pete airport.

Top guest favourite

Cottage in Indian Rocks Beach

4.97 out of 5 average rating, 132 reviews

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!

Superhost

Apartment in Belleair Beach

4.84 out of 5 average rating, 102 reviews

Studio On The Beach - Heated Pool - Self Check-in

☞ Free Parking ☞ Heated Pool ☞ Self-check-in We are located on the beach at 3200 Gulf Blvd, Belleair Beach. Features include a comfortable bedroom, free parking, and a heated pool. Essentials (linen, towels, toiletries) are provided at the start of your stay. We have no hidden fees or complicated checkout instructions.