Vacation rentals in Clearwater Beach Island

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Top-rated vacation rentals in Clearwater Beach Island

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Guest favorite

Apartment in Clearwater

4.93 out of 5 average rating, 58 reviews

Studio 4-The Waters' Edge-Sleeps 2

Relax in this calm, stylish space on the second floor. This smart and charming studio is perfect for a single traveler or a couple, with space for baby in a pack ‘n play. Prepare and enjoy 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.

Oct 24 – 31

$91 per night

Guest favorite

Apartment in Dunedin

4.97 out of 5 average rating, 36 reviews

407 1 Bedroom in Downtown Dunedin

This charming fully remodeled cottage 1BD/1BTH is located in the heart of Downtown Dunedin. *Easily walk to the water, shops, and restaurants! Gorgeous beaches like Caladesi and Honey Moon island are just minutes away! All major conveniences close by. *9 minutes from Toronto Blue Jays TD Ballpark *14 minutes from Clearwater Beach. *46 minutes from Busch Gardens Tampa Bay *32 minutes from Tampa International Airport *1 hr 45 min from Disney world, Orlando FL *41 min from St Pete Beach, Florida

May 5 – 12

$98 per night

Guest favorite

Apartment in Clearwater

4.99 out of 5 average rating, 352 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.

Jan 4 – 11

$130 per night

Guest favorite

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.

Sep 22 – 29

$85 per night

Guest favorite

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!!

Dec 14 – 21

$110 per night

Guest favorite

Home in Clearwater

5.0 out of 5 average rating, 111 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.

Sep 10 – 17

$505 per night

Guest favorite

Home in Clearwater

4.93 out of 5 average rating, 101 reviews

NEW! renovated duplex minutes from the Beach!

Welcome to the beautiful city of Clearwater, and to our newly renovated duplex home. Conveniently located within 0.5 miles or 7 minutes walking to clearwater downtown, and 3 miles or 7 minutes driving to the famous and award winning Clearwater beach. Easy access to local restaurants, bars, stores, and parks. This comfortable home features an open layout with modern decor, free WiFi, smart Roku TV, tile flooring and sleeps up to 6 people. It also offers free parking .

Oct 16 – 23

$106 per night

Guest favorite

Guesthouse in Clearwater

4.9 out of 5 average rating, 181 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!

Nov 11 – 18

$92 per night

Guest favorite

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.

Oct 14 – 21

$85 per night

Guest favorite

Apartment in Dunedin

4.96 out of 5 average rating, 184 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.

Nov 16 – 23

$93 per night

Guest favorite

Guesthouse in Clearwater

4.89 out of 5 average rating, 274 reviews

Studio close To Clearwater Beach

Welcome to Clearwater! Located just a short distance from a variety of restaurants, unique shops, and grocery stores, we offer convenient access to anything you might need during your stay. Our studio is 4 miles from Clearwater & 5 miles to Indian rocks Beach. There is no shortage of things to do in the area, local parks, museums, cruises, and a variety of nightlife. Enjoy jet skis, bike trails, tennis, parasailing, and pier fishing!

Jul 4 – 11

$82 per night

Guest favorite

Tiny home in Clearwater

4.98 out of 5 average rating, 93 reviews

Coastal Cottage Tiny Home - Bikes and Beach

This memorable place is anything but ordinary. This tiny house is perfect for 1 or two people to enjoy being close to the beach with bikes! It was completely renovated with beachy chic upgrades….the bedroom(Queen bed) living room/kitchen is perfect (like a studio) so you can enjoy your time away! Outside your own large deck with outdoor furniture. Sorry no pets/animals. Your own beach bikes, beach items etc. makes it a fun stay!

Jul 15 – 22

$69 per night