Vacation rentals in Clearwater Beach Island

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Top-rated vacation rentals in Clearwater Beach Island

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Guest favorite

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

Jun 6 – 13

G$16,481 GYD per night

Guest favorite

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

Aug 3 – 10

G$24,148 GYD per night

Guest favorite

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.

Oct 29 – Nov 5

G$20,215 GYD per night

Guest favorite

Home in Clearwater

4.9 out of 5 average rating, 61 reviews

New Charming Cottage by Dunedin & Clearwater Beach

An Adorable newly renovated cottage centrally located to Clearwater Beach and downtown Dunedin! This 2 bed 1 bath home is fully equipped to ensure your comfort. The cottage is just 10 min to Beach and 5 min to Dunedin. Spend a day on the beach, enjoy a variety of restaurants, breweries, coffee shops, and unique gift shops. Steps to the Trail; perfect for biking/walking. All in a beautiful neighborhood just a block off the bay. Substantial Discounts for Weekly/Monthly Sorry no Smoking ..dog ok

G$21,690 GYD per night

Guest favorite

Guest suite in Dunedin

4.94 out of 5 average rating, 202 reviews

Downtown Coastal Studio, 10 min. to the beach!

The studio has a bright and airy atmosphere, clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin in walking distance to the Pinellas Trail and Main St. Simply park your car and enjoy town on foot or rent a bike and cruise around. We are close to Honeymoon Island and Clearwater Beach (ranked in the top 15 white sand beaches in the world), the marina, a park just across the street with a nice path to stroll along the water or take in the sunset.

Sep 5 – 12

G$20,401 GYD 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.

Sep 14 – 21

G$28,560 GYD 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!!

Nov 30 – Dec 7

G$26,685 GYD per night

Superhost

Apartment in Clearwater

4.79 out of 5 average rating, 108 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

Aug 10 – 17

G$25,876 GYD per night

Guest favorite

Vacation home in Clearwater

4.9 out of 5 average rating, 111 reviews

Waterfront Courtyard Condo 2 Blocks to Beach

Renovated and conveniently located Clearwater Beach courtyard condo with water views of the Mandalay channel. Kitchenette and additional pull out sofa to easily accommodate additional guests if needed. Central location, being on the edge of residential and commercial districts, allowing for short walking distances to all popular attractions and food on Clearwater Beach. Watersports on-site with office, offering amazing Island Jet ski tours, kayak & paddleboard rentals, parasailing!

Oct 30 – Nov 6

G$24,914 GYD per night

Guest favorite

Home in Clearwater

4.92 out of 5 average rating, 50 reviews

Vintage Style (B) House minutes from the beach

Welcome to the beautiful city of Clearwater, and to our newly renovated Vintage Style 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 unique layout with Vintage-modern decor, free WiFi, smart TV, LVT flooring and sleeps up to 4 people. It also offers one free parking.

Dec 3 – 10

G$24,482 GYD per night

Guest favorite

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!

Nov 14 – 21

G$22,534 GYD per night

Guest favorite

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.

Nov 11 – 18

G$22,399 GYD per night