
Vacation rentals in Caladesi Island
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Top-rated vacation rentals in Caladesi Island
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THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.
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 and well-equipped beach home that has been completely remodeled. It sleeps 6 guests and offers 3 bedrooms, 2 bathrooms, an open kitchen and a cozy living/dining area with a sofa sleeper. You will love the secluded, tropical patio which offers a hot tub and a BBQ for relaxing moments. The property is located in a quiet and upscale, residential neighborhood of Clearwater North Beach, just across the street of the beautiful and pristine Gulf Beach. Clearwater Beach with its vibrant public beach life, various shopping opportunities and diverse restaurants is just a mile away. The House and Cottage can be BOOKED TOGETHER OR SEPARATELY and are the perfect place for families, family get togethers or romantic get-aways. It is NOT SUITABLE FOR SPRINGBREAKERS or any group that wants an environment that allows loud parties. THE AWARD-WINING GULF BEACH IS ONLY 32 STEPS AWAY! Grill, TVs, cable, WIFI, multiple driveways for parking, beautiful landscaping. Walk to shopping, dining or island attractions. Take the public trolley around the island or go as far south as Treasure Island! Check-in is 4:00pm or later; check-out is promptly at 10:00am to leave time for cleaning crew. 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.

Coastal Escape: heated saltwater pool & beaches
★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

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.

Comfy 1BR Near Beaches & Sponge Docks
Enter your private oasis & enjoy our spacious 1 bd in scenic Tarpon Springs. Relax on the comfy couch or oversized chair. Treat yourself to free snacks, cold water & coffee, tea or hot cocoa w/ the Keurig in the fully equipped kitchen! Enjoy a hot shower or bath. Extra toiletries supplied. Games & books available. Comfortable Queen size bed ensures a great sleep. Only 3 miles from Howard Park Beach & Sponge Docks. Sunset Beach 1.3 miles. Innisbrook Golf Resort 3.9 miles! Private Entrance

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

Tropical Oasis Retreat w/ Heated Pool
Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

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.

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.

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.

Walk to Main St and Waterfront, Mins to Beaches
Experience modern coastal luxury at this beautiful two bedroom first floor cottage in Downtown Dunedin. Steps from Main Street and minutes to stunning sunsets at the waterfront. Enjoy easy access to shops, restaurants, and nightlife. Make the short drive to award winning beaches- Honeymoon Island & Clearwater Beach. Thoughtfully designed and fully stocked for families, pets, and beach days. Treat yourself to the perfect charming coastal town getaway at the Barefoot Parrot Cottages.

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

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

Waterfront Condo - Sunset View of Tampa Bay

BEACHFRONT/Panoramic Views of the Gulf #201

Beautiful Beachfront 2-bedroom

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Beachfront Condo with Centerline Sunsets

Beach Front Madeira Beach

Amazing views on beachfront

Ocean Views - 15 Steps To The Sand - Book Now!
Caladesi Island house rentals

Heated Pool Oasis • 5mi Tarpon & Beaches

Lakefront home near beaches w/ waterview, pets ok

Waterfront Townhome w/Game Room & Boat Slip! Walk

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

Waterfront Pool Oasis •Kayak, Games & Sunset Views

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

Tropical Pool Retreat in Tarpon Springs

Palm Paradise - Family Amenities+Central Location
Beach house rentals in Caladesi Island

Charming Pet Friendly Beach Front Cottage with Uno

Beautiful New Home with Ocean View, Steps to Beach

Luxury 3 Bedroom Beach Home with Game Room!

WOW! Beach Front Cottage - Unbeatable Experience

Oceanfront 3/2 with 180 degree view BOOK NOW!

Oceanfront Boho Bungalow Breeze

Custom Waterfront 3BR Paradise/Salt WaterPool-Spa

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes
Destinations to explore
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- North Beach
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