Holiday houses in Clearwater Beach Island

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Top-rated holiday rentals in Clearwater Beach Island

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

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Guest favourite

Apartment in Clearwater

4.96 out of 5 average rating, 156 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

22–29 Aug

$239 NZD per night

Guest favourite

Apartment in Clearwater

4.9 out of 5 average rating, 59 reviews

Haven 7-The Waters' Edge-1 bedroom sleeps 4

Relax in this ground floor space. Situated on the bay, this retreat is a short walk from the beach, the recreation center, and all that Clearwater Beach has to offer. The spacious bedroom accommodates a king-size bed. Pull out sofa in living room is queen-size. The living room features hurricane-rated sliding doors that open to the deck and Clearwater Bay. Dining area seats four. Full galley style kitchen includes appliances and cutlery. Grill your fresh seafood outside. Jolley Trolley nearby.

6–13 Dec

$268 NZD per night

Guest favourite

Apartment in Clearwater

4.99 out of 5 average rating, 356 reviews

Private studio attached to house. Pool&bikes

Completely private A/C studio, bathroom & your own private saltwater pool. Studio attached to house. No cleaning fee. 1 block W to Edgewater trail. Beautiful sunsets on water. 1 block E to famous Pinellas trail. Stroll to downtown Dunedin or TD Stadium. Cruiser bikes provided. Drive, Uber, trolley or bike 4.5 miles to Clearwater Beach or Honeymoon Island. Near restaurants, shops, dancing, kayaking, fishing, boating, biking, baseball, etc! Space is not appropriate for under 18, pets, parties.

12–19 Dec

$256 NZD per night

Guest favourite

Home in Clearwater

5.0 out of 5 average rating, 114 reviews

Beach House

This house is a three bedroom, two bath, beach home that sleeps six people. It is on the beach as seen in the pictures. The porch which surrounds the house to the north and west side, gives you an expanded view of the beach and the Gulf of Mexico. The newly added front patio area expands out from the deck giving our guests a lounging area while overlooking the beach. You do not get any closer to the beach and you could not ask for a better place to enjoy your stay at Clearwater Beach.

14–21 Aug

$1,139 NZD per night

Guest favourite

Condo in Clearwater

4.92 out of 5 average rating, 232 reviews

Amazing views on beachfront

This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

2–9 Sep

$1,180 NZD per night

Guest favourite

Apartment in Clearwater

4.85 out of 5 average rating, 72 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

11–18 Dec

$259 NZD per night

Guest favourite

Condo in Clearwater

4.97 out of 5 average rating, 32 reviews

#1- Beautiful 2/2 Condo-Directly on the sand!

Kick back and relax in this calm & quiet beachfront condo, located directly on beautiful North Clearwater Beach! Unit is located on the 2nd floor with gorgeous views of the Gulf of Mexico. 2 Bedrooms, 2 bathrooms with a private balcony overlooking the beach. Sleeps 6 with the air mattress. WiFi included, Smart TV's, beach chairs, towels, toys, etc. Just bring yourselves and you are ready to go! Fully equipped full-sized kitchen with enough supplies to get you started!

24–31 Oct

$746 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

$233 NZD per night

Guest favourite

Apartment in Dunedin

4.96 out of 5 average rating, 186 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.

29 Apr – 6 May

$229 NZD per night

Guest favourite

Hotel room in Clearwater Beach

4.78 out of 5 average rating, 469 reviews

Bay Loft Apartment 2

Our goal is to preserve the old Florida and to offer you the opportunity to experience a stay at a vintage themed motel. Our Airbnbs are all unique. Some include neon signs, some the original colorful subway tiles, and others terrazzo floors. You will be staying at the exact Airbnb as pictured on the listing. We seek to keep the properties original and authentic by implementing repairs instead of replacements.

1–8 Nov

$170 NZD per night

Guest favourite

Apartment in Clearwater

4.86 out of 5 average rating, 104 reviews

Coastal Waterview Condo 2 Blocks to Beach

Wake up to your own water view with our comfortable direct waterfront 1 bedroom 1 bath villa on world-famous Clearwater Beach! Quiet & centrally located neighborhood on the edge of residential and commercial districts allowing for easy walking distance to everything on Clearwater Beach. Watersports on-site with office, offering amazing Island Jet ski tours, kayak & paddleboard rentals, parasailing!

20–27 Aug

$265 NZD per night

Guest favourite

Guesthouse in Dunedin

4.99 out of 5 average rating, 140 reviews

Bay Suite in Heart of Dunedin

Gorgeous, contemporary apartment located only a few blocks away from Main Street and a five-minute walk from the Pinellas Trail. The space has an open living/dining room with incredible vaulted shiplap ceilings. Feel light and open with large windows overlooking the majestic grand oak trees.

9–16 Sep

$278 NZD per night