
Holiday rentals in Caladesi Island
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Top-rated holiday rentals in Caladesi Island
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THE HOUSE - 32 Steps to the Beach - Beautiful Clea
House sleeps 6 - Private patio and Hot Tub, Wifi, Grill . '32 Steps to the Beach' is a charming and cozy Clearwater Beach retreat in a TOP LOCATION. The pristine Gulf Beach is just across the street! We also have a Cottage at the same address and they can be rented separately or together. Covid-19 UPDATE - See below. To book the House & Cottage or the Cottage on its own please see the links to their descriptions at the right of this page. THE HOUSE is a tastefully decorated, upscale
4.98 out of 5 average rating, 152 reviews
Wonderful family friendly home in Dunedin FL
Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caladesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.
4.92 out of 5 average rating, 285 reviews
Palm Haus • Heated Pool • Near Beach • Game Room
Charming home with stylish baths & bedrooms. Heated pool included in the price. Gas fire-pit, outdoor games, large secluded backyard! Game room! Near Honeymoon Beach & Caladesi Island open for sunbathing & water sports; historic downtown Dunedin with cute shops, cafes, restaurants & cultural events. The area has a number of top-notch golf courses and trails. Palm Harbor's welcoming community & mild climate make it an ideal getaway for outdoor adventures, cultural experiences, and coastal views.
4.99 out of 5 average rating, 132 reviews
Surf Shack Tiny Home on Pinellas Trail w/ Heated P
Welcome to the Dunedin Tiny House Vacation Rentals! This Vacation Rental property offers daily, weekly or monthly rentals in 4 luxury tiny homes, a 3 bed bungalow & 1 bed cottage. The 6 Units along with a large Heated Pool are all tucked away within a thoughtfully planned, peaceful & wooded lot.... located right on the Pinellas Trail! The front entrance is conveniently located on Bayshore Blvd just north of the crossroad of Wilson. Once you enter the front door of your unit you will enjoy a
4.95 out of 5 average rating, 105 reviews
Steps to Downtown, Mins. to Waterfront | Sleeps 8
Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to stunning sunsets, shops, dining, breweries, and Pinellas Trail. Perfect for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this Dunedin favorite today !
4.98 out of 5 average rating, 365 reviews
Artisan Island Bungalow / Walk To Downtown
* HOSTED BY GABE & SHANNON * Enjoy your visit to Dunedin (& surrounding areas) in our custom renovated bungalow! Originally built in 1918, this home has been painstakingly revived to reflect our thriving creative community. Much of the home has been built and decorated using the skills of local artisans. Many things - from the front deck to the furniture to the very plates you’ll eat off of - are handcrafted originals. This isn’t just a place to crash. It's a living, breathing work of art.
4.93 out of 5 average rating, 177 reviews
Dunedin private pool oasis-Cozy Coastal Cottage
100-5★ reviews! Cozy Coastal Cottage is your private tropical escape just 2 blocks from Dunedin’s Main Street. Relax by the sparkling pool, then walk to restaurants, breweries, shops, the marina, and Pinellas Trail. Located in the historic district, you’re minutes from top-rated beaches and the Blue Jays stadium. Enjoy a full kitchen, walk-in shower, fast Wi-Fi, A/C, laundry, and beach gear for the perfect Gulf Coast getaway. Pool days, sunset walks, and downtown nights - all waiting for you.
4.99 out of 5 average rating, 100 reviews
Luxe Private Waterfront Getaway with Pool in Ozona
Awesome single family inter-coastal waterfront home with boat dock and pool. 1800 square feet of luxury, 3 bedroom, 2 bathroom, sleeps 10 people in beds. Master bedroom overlooking the water and pool with king bed. Second bedroom with 1 queen bed. Third bedroom with 1 queen bed. Living-room has 2 queen pull out beds and a large glass door wall that opens up to the spacious screen enclosed pool patio. Full kitchen, dining room, living room, laundry area with washer/dryer. Dock has deep water.
4.93 out of 5 average rating, 106 reviews
Tropical Getaway w/Heated Pool & King Beds
Welcome to our sun-kissed getaway in sunny Palm Harbor! You'll find a fully stocked kitchen, a private heated pool, and comfortable accommodations for up to 6 guests. Whether relaxing on one of our award-winning beaches, playing a round of golf, or exploring Tampa Bay's fun spots, there's something for everyone to enjoy. Just a quick note: Because of a family member's allergies, we're not able to allow any animals on the property, including ESAs. Thanks so much for understanding!
4.95 out of 5 average rating, 183 reviews
Tropical Paradise
Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping
4.99 out of 5 average rating, 276 reviews
Pvt Pool, Free Kayaks, Wlk to Gulf, Fish, Bike Trl
Escape to your private Palm Harbor oasis! This studio, offers complete privacy with a cozy queen bed, sofa bed, and kitchenette. Enjoy the sparkling in-ground pool reserved for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or explore the nearby Pinellas Trail. Enjoy beaches, dining, breweries, and live music minutes away. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.
4.99 out of 5 average rating, 127 reviews
Quiet Locale King Beds 1 Mile To Honeymoon Island
Welcome to Mai Tai Suites Dunedin With over 240 online reviews ☞ 2 King Beds ☞ Parking Onsite 1 Space ☞ No Cleaning Fee ☞ Wifi ☞ 2 Smart TVs (largest is 65 inches) ☞ Dog Friendly ☞ Fully Equipped + Stocked Kitchen ☞ Self Check-In ☞ Onsite Washer + Dryer ☞ Beach Towels & Cooler Provided 》35 Mins to airport 》2 Mins to Honeymoon Island 》15 Mins to Clearwater Beach 》 Not Small Child Friendly age 13+ is OK
4.94 out of 5 average rating, 31 reviewsPopular amenities for Caladesi Island holiday rentals
Other great holiday rentals in Caladesi Island

Walk Downtown & Waterfront | Dunedin's Best Street
4.95 out of 5 average rating, 20 reviews
Rooftop+Balcony- Luxury Stay in Downtown Dunedin
5.0 out of 5 average rating, 54 reviews
Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes
5.0 out of 5 average rating, 47 reviews
Studio King Sunset at Beso Del Sol (Pool/Hot Tub)
4.95 out of 5 average rating, 56 reviews
Seaside Top Floor Condo
4.75 out of 5 average rating, 83 reviews
Condor's Nest-Walk to Downtown, Heated Pool!
4.96 out of 5 average rating, 49 reviews
Dunedin Roost 2BR Home Chef Kitchen near Downtown
5.0 out of 5 average rating, 6 reviews
Dunedin Bliss! Walk to Ballpark, Downtown & Water!
4.79 out of 5 average rating, 28 reviewsDestinations to explore
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