
Vacation rentals in Caladesi Island
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Top-rated vacation rentals in Caladesi Island
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The Cottage - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill. Just Steps from the beach.
Our tastefully decorated and cozy Cottage offers everything you need for a romantic get-away and a relaxing stay in sunny Clearwater Beach. The Cottage is part of our vacation property '32 Steps to the Beach' which consists of a 3 bedroom house and a separate 1 bedroom cottage. The Cottage can be booked separately or together with the House. To book The House or House & Cottage together please see the listings at the side of this page. Covid-19 UPDATE - See below. The Cottage is located in a quiet and idyllic residential neighbourhood of Clearwater North Beach. The beautiful, award-winning and pristine Gulf Beach is just steps away from the house. If you prefer to have a calm beach day away from the crowds this is where you want to stay. Clearwater Beach with its vibrant public beach life and diverse restaurants is just a mile away. The Cottage offers a spacious, elegant room with a queen bed, a sitting area with a sofa sleeper and a remodeled bathroom. The new kitchenette gives you the opportunity to prepare meals and enjoy them in the small dining area or outside on the secluded patio. Savour a cup of coffee in the morning, a glass of wine after a relaxing day on the beach or enjoy a BBQ in the backyard. Clearwater North Beach is an upscale, safe residential neighborhood that welcomes families and couples. It is not suitable for 'spring breakers' or any group that wants an environment that allows loud parties. The area of Clearwater offers an astonishing diversity of leisure activities. If you enjoy sports you might want to try out the numerous jogging, skating, biking, golfing, hiking, swimming, surfing, tennis or fitness opportunities. In Florida's state parks and on the breathtaking beaches you will experience the beauty and serenity of nature. Several theme parks guarantee fun for the whole family and the diversity of the many restaurants in the area will surprise you. From casual to upscale dining, from local and national to international cuisine - you will find it all! Please also visit our website for more information about our Clearwater Beach homes, Clearwater Beach and the area: www.clearwater-beach-vacations.net Check-in is 4:00pm or later; check-out is promptly at 10:00am to leave time for cleaning crew. We will be happy to answer all of your questions. When using the 'Book it Now' button please include information on the ages and number of people in your party to help us make a quick decision on your request. IMPORTANT: We do not advertise on Craigslist! Be safe and only deal with the owner. COVID-19 Pinellas County is open for short term vacation rentals with guidelines that we are following in full. We take the safety of our guest and cleaning staff extremely seriously. Our cleaning crews are using sanitizer and disinfectant on all surfaces before your arrival and as cleaning is taking longer than previously it is unlikely that we can offer early check-ins or late checkouts. Our houses have well equipped kitchens and we believe that separate units are the best option for vacationing in the time of Covid-19. Florida is seeing an increase in cases at the moment and we stress the importance of guests taking travel insurance that would cover them in the event that they no longer want to travel to Florida. In the event that the administration halts vacation rentals we would of course refund guests as we could no longer accept them. We have to stress that after two months of cancellations and re-bookings we will not be able to offer refunds if Clearwater Beach remains open for vacation rentals but guests decide not to travel.

Blue Moon Dome > Cozy Romantic Beach Retreat
• Full private dome house. • Walk to Florida Botanical Gardens & Pinellas Trail • 7 min to white-sand beaches, restaurants, cafes, shopping • Romantic queen bed under a skylit dome • Airy, cozy, filled with light - a perfect escape from the ordinary • Fast Wi-Fi, kitchen, private entry, free parking • Optional romantic room setups with candles, petals & treats Whether it’s a honeymoon, birthday surprise, solo reset, or anniversary adventure - Blue Moon Dome is more than a stay. It’s a memory.

salt living at its best
- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

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.

Private Beachfront 2BR BUNGALOW*POOL*PETS ok
DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows + heated pool

Guest House in prime location!
This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

Bay Lake Cottage
You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Beautiful Beachfront Cottage on the Water
Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Luxury Beach Bungalow | Walk to Dining & Sunset
Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Bayside Retreat your tropical oasis
"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Private Ocean View Beach Retreat with Balcony
Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

Tiki Hut Cottage
This unit private vacation rental is privately located on the property, plenty of space for 4 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom has a walk in shower with stack washer and dryer. Spacious living area with a kitchenette. The property is an acre of lush tropical plants Conveniently located to the downtown & beach.All our units are non-smoking and vaping.
Popular amenities for Caladesi Island vacation rentals
Caladesi Island beach vacation rentals

Quiet Beachfront Bungalow on Florida’s Gulf Coast

COASTAL CHIC! Luxury Apartment with Oceanviews

BEACHFRONT/Panoramic Views of the Gulf #201

Casa de B.O.B ... Best on Beach

Indian Shores Gulf Front Rental

Christmas Sale!-Ocean Views!-15 Steps To The Sand!

♥ OCEANFRONT VIEW ♥ BEACHFRONT CONDO ♥ NEW ♥ U3 ♥

*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
Caladesi Island house rentals

Ocean Sunsets & Downtown Biking Trails

Feels Like Home - 3/2 pool home that sleeps 6

Ocean Dreaming: Waterfront Home with Heated Pool,

FLOH - delightful days in Dunedin!

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

Downtown Dunedin: Golf cart, Bikes, Brewery,Marina

Tree House Treasure

Swim-Out Bedrooms, Waterfall pool, Peace Place
Beach house rentals in Caladesi Island

Beautiful New Home with Ocean View, Steps to Beach

Luxury 3 Bedroom Beach Home with Game Room!

Oceanfront 3/2 with 180 degree view BOOK NOW!

Custom Waterfront 3BR Paradise/Salt WaterPool-Spa

Oceanfront Boho Bungalow Breeze

Sunshine Beach Bungalow That Is a Unique Treasure

Casa Del Sol | Private Beachfront, Pool Table

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes
Destinations to explore
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- North Beach
- Tampa Palms Golf & Country Club
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