Holiday houses in Clearwater Beach Island

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Top-rated holiday rentals in Clearwater Beach Island

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Guest favourite

Guesthouse in Clearwater

4.92 out of 5 average rating, 332 reviews

Clearwater Guesthouse w/ King Bed, Near Beaches

This private home away from home sits behind the main house in a quiet neighborhood conveniently located near downtown Clearwater, Clearwater Beach, Tampa, St Petersburg, Dunedin, Tarpon Springs, and other great towns. Located near Beaches, restaurants, shopping, & entertainment venues. • Clearwater Beach= 4 miles / 8 minutes • Downtown Dunedin= 3 miles • Honeymoon Island= 9 miles • Tarpon Springs Sponge docks= 14 miles • Tampa Airport (TPA)= 14 miles • St Pete/Clearwater Airport (PIE)= 9 miles

6–13 Jun

$169 NZD per night

Guest favourite

Apartment in Clearwater

4.95 out of 5 average rating, 154 reviews

Private Apt, Beach 2 mi, Walk to Park & Downtown

Beautifully remodeled 1930s apartment in a small building. Situated in a gorgeous, historic, walkable neighborhood. Only two short miles to Clearwater Beach. Walk or jog throughout the neighborhood, to Coachman Park, downtown, or over the bridge leading to Clearwater Beach. Two bicycles are usually available for guests. We are in close proximity to restaurants & cafes. Many of our guests attend concerts at The Sound at Coachman Park and shows at the Capitol Theatre. Animals are not permitted

26 Sep – 3 Oct

$240 NZD per night

Guest favourite

Apartment in Clearwater Beach

4.95 out of 5 average rating, 63 reviews

Studio 2-The Waters' Edge-Sleeps 2

Kick back and relax in this second floor space. This charming studio features king size bed and is perfect for a single traveler or a couple, with space for baby in a pack ‘n play. Prepare your snacks and meals in the kitchenette or grill fresh, local seafood on the patio bayside. This location allows you to enjoy water views from our bayfront dock and the Mid-Century small-town charm nearby. Situated just blocks from the beach with several restaurants and entertainment. Jolley Trolley nearby.

26 Oct – 2 Nov

$228 NZD per night

Guest favourite

Home in Dunedin

4.96 out of 5 average rating, 206 reviews

FLOH - delightful days in Dunedin!

Cute quaint house with 2 bedrooms, 1 bath, located in downtown Dunedin Florida. All furniture in the house is new. Bathroom is newly remodeled, and includes a shower with a jet tub. Cozy family room with 60" flat screen smart TV, and sleeper sofa. We have a desk, and elliptical machine, along with a comfy chair for reading/relaxing in the extra room on the back. The kitchen is fully functional, with most conveniences of home. Come and enjoy delightful Dunedin, and have the time of your life!

30 May – 6 Jun

$239 NZD per night

Guest favourite

Guest suite in Dunedin

4.94 out of 5 average rating, 202 reviews

Downtown Coastal Studio

Our Downtown Coastal Studio was recently renovated. The studio has a bright and airy atmosphere. Both clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin and two blocks to the Pinellas Trail. Simply park your car and enjoy downtown on foot or rent a bike and cruise around. We are close to two major beaches, the marina, and John G. Hubbard Park, which is just across the street with a nice path to stroll along the water or take in the sunset.

8–15 Jun

$201 NZD per night

Guest favourite

Condo in Clearwater

5.0 out of 5 average rating, 5 reviews

Wonderful Condo Fully Renovated! - Ground Level!

Ground Floor Completely RENOVATED!!! Amazing & Very cozy and it has a a 60” Fireplace. 1 king size bed and a queen pullout couch new style, 1 bathroom with the best water pressure including a rain shower and a hand held unit. This unit is very well equipped with everything you need and have at your home. The condo is great for a couple’s getaway or a nice family vacation. YOUR HOME AWAY FROM HOME!! Steps to the POOL, beach chairs, Floaties, wagon, cooler, etc. The Beach is a 10 minutes!!

14–21 Nov

$272 NZD per night

Guest favourite

Home in Clearwater

4.9 out of 5 average rating, 116 reviews

Coastal Cottage B - Bikes Beach Items

This lovely 2 bedroom 1 bath home is clean and modern! This home is a duplex but has no access between units -it was triple insulated on all walls. All bedrooms have brand new foam mattresses and new cold air/mini splits. This unit has many stairs-please see pictures. Access to the bathroom is through the downstairs bedroom. I just installed privacy curtains in both bedrooms (no actual bedroom solid doors. Sorry no animals/pets. Close to Dunedin, Honeymoon Island, and Clearwater beach! ❤️

26 Oct – 2 Nov

$240 NZD per night

Guest favourite

Apartment in Clearwater

4.86 out of 5 average rating, 70 reviews

☀Pool✔ Kitchen✔ Beach✔ Self Checkin✔ Free Parking✔

No hidden fees! No complicated checkout instructions! We make it easy for our guests. ☞ 2 min walk to the beach ☞ Free parking ☞ Heated pool ☞ AC ☞ Self check-in We provide essentials (linen, towels, toilet paper, shampoo, soap, etc.) at the beginning of your stay. We recommend getting more supplies for more extended stays. 648 Poinsettia Ave Clearwater Beach 33767 Location, location, location! 500 feet to the beach 500 feet to a park and playground 0.2 mile to public tennis courts

16–23 Nov

$231 NZD per night

Guest favourite

Condo in Clearwater

4.89 out of 5 average rating, 165 reviews

Happy getaway nest. Very cozy & high quality

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 feel at home in my place because I take care myself.

3–10 Oct

$239 NZD per night

Guest favourite

Guesthouse in Clearwater

4.9 out of 5 average rating, 182 reviews

Cottage on Pinellas Bike Trail

This cottage on the trail is a gem. It is an easy one mile bicycle ride to downtown Dunedin and a quick stroll to waterfront Edgewater Park to watch sunsets or see the lights of Clearwater Beach across the intracoastal waterway. Circular driveway with a carport for off street parking. The cottage is equipped with a Keurig, microwave, mini fridge, as well as beach amenities and wifi. There's a fenced back patio for you to enjoy our beautiful weather!

10–17 Jan

$232 NZD per night

Guest favourite

Guesthouse in Dunedin

4.92 out of 5 average rating, 78 reviews

Oceanside Timeless Escape Cottage

The best time of the year is right around the corner! Come visit and enjoy a walk down the street to the ocean for that cool ocean breeze. Free Bikes, BBQ Grill, beach supplies, backyard lounge area, outdoor Jenga, cornhole and hosts that go above and beyond to make sure you LOVE your stay. You cannot beat this location. Fully remodeled home and Walking distance to vibrant downtown Dunedin with plenty of shops/bars/breweries/restaurants/playgrounds.

18–25 Oct

$212 NZD per night

Guest favourite

Apartment in Dunedin

4.96 out of 5 average rating, 185 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.

9–16 Oct

$218 NZD per night