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Cleawater Vacation Rentals

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717 rentals are available

  • This sprawling vacation home has 7 bedrooms, 5 full bathrooms, a dipping pool, endless porches, terraces and a fabulous roof deck that overlooks the gulf.

    With comfortable sleeping accommodations for 24 guests, this 7 bedroom exquisite home is perfect for a large family getaway.

    Our White Sands Retreat is composed of a 4 bedroom house, a 2 bedroom cottage and a 1 bedroom suite. Each property has a living, dining and a fully equipped kitchen area. All units all share a dipping infinity pool and the common grounds. The units can be booked together or separate, please check our calendar for availability and rates.

    Our White Sands Retreat was designed for entertaining and would be a great location for multi-family vacations, large groups, events, weddings or corporate retreats.

    The total square footage for the whole retreat combined is 4000 sq ft. this beach compound offers both comfort and sophistication.

    This rare 4-story beach home is one of a kind in Clearwater Beach as it is located in a quiet street and 30 seconds from the gulf but still walking distance to all activities and restaurants in the area.

    Our beach retreat is well stocked with all of the essentials needed for a family vacation. This great beach rental compound has been upgraded and has all new décor and appliances.

    If you have a large group or multiple families looking to stay in Clearwater Beach, White Sands Retreat may be for you.

    The White Sands House is composed of 4 bedrooms, 3 bathrooms accommodating a total of 14 guests comfortably. This gorgeous beach home has 4 levels, 2 living areas, a fully equipped kitchen, a dining area and balconies where you can enjoy the gulf views.

    The Driftwood Cottage is composed of 2 bedrooms, 1 bathroom accommodating a total of 6 guests comfortably. This elegant beach cottage is a one-story rental with a fully equipped kitchen and adjoining living and dining areas.

    The Sea Turtle Suite is a one-bedroom rental located on the second floor of the retreat. It features a living, dining and kitchen area with a partial gulf view.

    Our White Sand Retreat is one of our best selections of vacation home rentals in Clearwater Beach. It is one of the few larger homes that are zoned short-term rentals and the closest one to the beach.

    ** Please note: The units can be rented together or separately. Please note a total of 5 parking spots are available for all units.

    Square Footage: 4000 Square Feet.

    Clearwater
  • Our vacation condo offers an excellent location in Clearwater Beach. This completely furnished unit is located on Mandalay Ave, across the street from the Hilton and a short distance to the Pier and the beach.

    If you are looking for a nice quality well-appointed and clean condo you have found it. Accommodations include 2 bedrooms and 2 bathrooms. Master bedroom has a Queen-sized bed and in the second bedroom a Queen-size bed to comfortably accommodate 4 adults.

    You can expect a great stay in this cute 2 bedroom/2bath unit.

    Conveniences include a fully-equipped kitchen, all linens, washer/dryer in unit, wifi and much more. The unit is stocked with everything you could possibly want or need. Our beautiful condo is light & airy, and thoughtfully complete with everything you need to make your time in Clearwater Beach perfect.

    This beautiful condo has a small balcony that has partial intercoastal view and is across from Cooters Restaurant.

    We know that you will enjoy staying in our little bit of paradise.

    We knew that the location were what guests would love & why they would want to return again in the future.

    Convenient to restaurants, shops, movie theater and golf and much more. Located at right by the pier, this condo is the perfect retreat for couples. Close enough to water sports, fishing and shopping. Everything is within reach yet this condo is in a quiet area.

    Things to keep in mind. The address of this condo is on Mandalay Ave but the physical entrance is in Poinsettia across from Cooters Restaurant.

    The condo is located on the second floor and there is no elevator. To walk to the beach you have to go around the building and cross Mandalay Ave.

    Clearwater
  • These lofts are the perfect vacation destination with a beautifully decorated floor plan that incorporates sophisticated beach comfort with a blend of an elegant boutique suite.

    The well-appointed kitchens have stainless steel appliances, and fully equipped with the necessities to make your stay easy and enjoyable. The adjoining living and dining areas are light and airy that open to a balcony with both beach and bay views. The beach, restaurants, coffee shops, beach shops and fresco dining are just a stroll away.

    Clearwater
  • These lofts are the perfect vacation destination with a beautifully decorated floor plan that incorporates sophisticated beach comfort with a blend of an elegant boutique suite.

    The well-appointed kitchens have stainless steel appliances, and fully equipped with the necessities to make your stay easy and enjoyable. The adjoining living and dining areas are light and airy that open to a balcony with both beach and bay views. The beach, restaurants, coffee shops, beach shops and fresco dining are just a stroll away.

    Clearwater
  • Our Bruce Cabana and Guesthouse is a quaint and cozy home and bungalow that is ideal for your Clearwater Beach Island getaway filled with a shared tropical yard and a beautiful pool.

    The Bruce rental home is a charming 3 bedroom 1 bath home that will accommodate 8 guests total.

    The Guesthouse bungalow is a 1 bedroom 1 bath that will accommodate 4 guests total. Total these two will accomodate 12 guests.

    This ideally designed floorplan of a single home and a guesthouse offers you and your family an affordable option of renting two separate places as one.

    This set up has all of the comforts of home, each equipped with a dining and living area, fully equipped kitchen and much more.

    This lovely rental is just 2 blocks from the beach.

    The sleeping arrangements in the Cabana include a Queen size bed in the first bedroom, two Queen size beds in the second bedroom and a set of bunk beds in the third bedroom to accommodate 8 guests. The sleeping arrangements in the Bungalow include a Queen size bed and a pull out couch to accommodate 4 guests for a total of 12 between both rentals.

    Each rental property is beautifully decorated inside and out for a cozy, sunny, beachy stay.

    In addition, these vacation rentals have an exceptional location in a peaceful neighborhood setting.

    You won't be disappointed with this beach set up that includes lots of space for pool side relaxation, a large shared paver area, lounge chairs and a shared tropical pool area.

    Please keep in mind that Bruce Cabana and Lantana Cabana make up the Clearwater Beach Cabana which can be rented separately or together. If rented separately the courtyard and pool area is shared.

    Clearwater
  • Stunning vacation rental located in North Clearwater Beach – the most sought area of all travelers!

    This is one of the 31 grandfathered rental properties that can be rented weekly!

    Located just two blocks from the white sand, this spacious vacation house is a perfect escape for you and your family featuring a shared lagoon style pool with a large courtyard.

    This gorgeous open home features 3 bedrooms and 2 bathrooms to comfortably accommodate 12 guests.

    Our beach cabana has a newly remodeled gourmet kitchen, large dining area, living room and a family room which gives a family plenty of space to spread out.

    First bedroom has a queen size bed, second bedroom has a queen size bed and third bedroom has two queen size beds. Living and family areas have a total 2 pull out sofas which gives a total of sleeping arrangements for 12 guests.

    There are two bathrooms, one with a walk in shower and the second one with a shower/tub combination.

    The formal dining room seats 8 people and the kitchen bar seats another 3. Family room has a door that leads to the beautiful courtyard with a magnificent shared pool, plenty of tables and chairs, bbq grill and much more.

    The patio and pool area are embedded in a tropical, secluded back yard that is shared with another 3 bdroom house across from the pool.

    This Clearwater Beach Home is the perfect place for families, couples and snowbirds.

    A short walk brings you to Pier 60, where each and every day you can enjoy the exciting sunset celebration.

    Please keep in mind that Bruce Cabana and Lantana Cabana make up the Clearwater Beach Cabana which can be rented separately or together. If rented separately the courtyard and pool area is shared.

    Cleawater 3.55 miles
  • Beautifully decorated Dockside 605's shared balcony provides access to the unit overlooks the intra-coastal waters and the liveliness of all of the boats, dolphins, birds and such that inhabit it. Classy touches like pocket lighting in the kitchen, granite counter tops, stainless steel appliances, stacked washer and dryer, dark woods, comfortable furniture and Victorian headboards make 605 a vacation rental for the discriminating vacationer. The bedrooms each have TVs and DVD players. Spend your vacation in style, luxury and convenience! The Dockside Condos are located in the heart of the South Clearwater Beach area.

    Clearwater Beach 2.96 miles
  • These lofts are the perfect vacation destination with a beautifully decorated floor plan that incorporates sophisticated beach comfort with a blend of an elegant boutique suite.

    The well-appointed kitchens have stainless steel appliances, and fully equipped with the necessities to make your stay easy and enjoyable. The adjoining living and dining areas are light and airy that open to a balcony with both beach and bay views. The beach, restaurants, coffee shops, beach shops and fresco dining are just a stroll away.

    Clearwater
  • This quaint 1 bedroom has 1 bathroom, offers privacy and is only steps away to the bay areas famous beach - CLEARWATER! This beach getaway will comfortably sleep 2 people!

    Clearwater
  • This charming 2-BR unit offering an area for grilling and chilling! Enjoy the charm of this nicely decorated tropical beach apartment! Nestled in the Tourist District of North Clearwater Beach you are only a few blocks over to the white sands and blue waters of Clearwater Beach as well as the restaurants and beach shops. Get ready folks to relax and unwind.

    Clearwater
  • This gulf front, classically designed condominium offers you the chance to enjoy a quiet and relaxing vacation with nothing but the peaceful sea breeze outside your windows. Our Beachfront Beauty Condo is a tastefully decorated 2 bedroom/2 bath gulf front rental with wonderful views of the ocean.

    The beachfront condo provides guests with large living room and a breakfast bar. This beachfront unit has a private balcony in the living area and master bedroom to provide you with breathtaking views out to the ocean and of Florida sunsets.

    The rental has a fully equipped kitchen for a gourmet meal with your family.

    The Master bedroom features a King size bed, while the second bedroom has two single beds. There is also a queen sleeper sofa in the living room. This rental sleeps 6 guests comfortable. Our Beachfront Beauty Condo provides guests with the amenities that will make their stay an enjoyable one.

    This gulf front condo has beautiful scenery and is located in a unique little beach community. The beautiful exterior, great location, and extensive amenities are just a few reasons why this is one of the best beachfront condos in the area. No backyard can compare to dolphins playing in water and soft waves lapping the shore in the Beachfront Beauty Condo.

    Clearwater
  • Infinity Sun Beach House, located on one of Clearwater Beach's newest waterfront communities, introduces a magnificent coastal contemporary townhomes with British Colonial influences constructed to the most current building standards and codes while promoting energy efficiency. Each residence features a 2 car garage, 10' ceilings, crown molding, 16 ft. sliding doors that open up onto expansive private balconies providing stunning unobstructed water views. The stately kitchens with large center islands are designed for easy entertaining equipped with Kitchen Aid stainless steel appliances, custom cabinetry, & silestone quartz counter tops. Community features include a resort style pool and spa, gas grills with outdoor entertaining area, and a beach rinse off station. This beautiful townhome is located alongside the #1 rated beach in the US and is in the center of everything Clearwater Beach has to offer; recreation, shopping, fine dining and nightlife. Two international airports 30-40 minutes away.

    Clearwater
  • The Residences at Sandpearl is truly a rare gem nestled in the sugary white sand of the award-winning Clearwater Beach (named Best Beach Town by USA Today). This upscale complex offers world-class resort amenities and direct access to the beach. The palatial pool and garden deck overlooks the ocean from the third story. The heated resort style pool is long enough for lap swimming. An eight person whirlpool spa is situated next to the private pool along with several covered cabanas for protection from the sun, gas grills and outdoor showers for rinsing off. Unlike most hotels, with Sandpearl's spacious, well equipped pool deck you will never have a problem finding a lounge chair to bask in the Florida sunshine.

     

    Just off the pool is a posh club room with full catering kitchen, social rooms, billiard room, boardroom and state-of-the-art fitness center with cardio machines equipped with their own TVs, weight machines, sauna and steam room, 24-hour manned and gated security, and a full-time concierge. This 24 hour concierge service is incredible with friendly, helpful staff ready to provide for whatever you may need. Free coffee is served daily as an added perk. If you really want to treat yourself, allow room service to prepare you a meal from the renowned Caretta restaurant or contact the concierge to arrange an unforgettable private dining experience on your very own balcony!

     

    The 4 Diamond Sandpearl Resort & Spa (rated #8 Worldwide by Expedia Insider's Select) next door has a beautiful spa where you can pamper yourself to facials, pedicures, manicures and massages. There is also a beach-side café (Tate Grill) with live entertainment and even a fire-pit nuzzled in the dunes, not to mention the city's only AAA 4 Diamond restaurant, Caretta on the Gulf. If you have more guests in town than beds in the unit, this property provides exceptional accommodations.

     

    The convenient location of the Residences means you can walk to the area's fabulous restaurants, listen to live music & watch the sunset at Pier 60, and experience all the water activities Clearwater Beach & Marina have to offer (like Dolphin & Pirate Cruises, jet-skis, charter boat fishing and para-sailing). With the Sandpearl Resort right next door, as well as the beach, dining, shopping, and nightlife just steps away, you won't even need to get into your car (securely parked in parking garage). Farther away you can enjoy several top-notch golf courses, world-class museums (Dali in St. Petersburg) and professional sporting events (Rays, Buccaneers and Lightning).

    Clearwater
  • Magnificent Waterfront Home will all Amenities in The Exclusive Island Estates Area of Clearwater Beach, Florida. Fully Furnished w/ Pool * Boat Dock

     

    A beautifully decorated beach home on Island Estates in the #1 Rated Beach Area with White Sandy Beaches only moments away. This Home also offers a Beautiful Private Pool and Large Patio & BBQ setting with Gas and Electric Grills made for Entertaining. 2 Master Suites with King Size Beds with views over-looking the water way, and 2 Additional Bedrooms with Queen Size Beds. Private Dock for your Boat, Fishing, Jet Skies.

     

    Your Dream Vacation House Includes all the Special Items and Furnishings you'll need to make your visit a pleasure. These are but a few of the items you'll find: 2 Big Screen T.V.'s, Cable, Internet Service, and Complete Sound System, All bedding and linens, Fully Stocked Kitchen Ware to Cook With, Full Size Washer & Dryer, 2 Car Garage, Large In-Ground Private Pool and Patio in the backyard, and Bring your Boat and use the private dock off the canal. This Home has been completely furnished with New Beds, Dressers, Big Screen T.V.'s, Linens, Table & Cook Ware, Outdoor Patio & Dining Set, Living Room Furniture. Located minutes to Great Restaurants, Shopping, Attractions, and Short Distance by Bike, Walk, or you can take the local Trolley (two dollar) to Beautiful Clearwater Beach.

     

    Make Your Dreams Come True and Let The Dreams of a Lifetime Happen Here at Island Estates Vacation Home!

    Clearwater
  • S909 at the Regatta Beach Club is your host to an unforgetable vacation experience!

     

    This Is What Beach Living Is All About, Just Steps Away From Having Your Toes In The Sand!!

     

    Living at the Regatta Beach Club will make you feel like you are on a permanent vacation! The beach here is beautiful and it feels like a private resort. The beautiful Olympic sized heated pool is right of the beach. It has plenty of seating, and BBQ grills just off the pool area. There are also tables and chairs adjacent to the pool where you can have your dinner or a snack. There is a private pier too where you can sunbathe, or sit and watch the surf.

     

    The main lobby has lots of seating and a full time reception desk and 24 hour concierge services. There is a well equipped fitness center, theater room, billiard table, and there is even foosball and table tennis!

     

    What's Nearby

     

    Popular Pier 60 is just a mile and south off of Mandalay Avenue. It is in the heart of Clearwater Beach with lots of great dining and entertainment choices. Its fun to just walk around, go out on the Pier (there is a small fee), watch the street performers, or catch a Sunset Movie.

     

    Why People Live in Regatta Beach Club Clearwater Beach

     

    Regatta Beach Club residents just love the beautiful uncrowded beach, all the great amenities and easy access to the heart of Clearwater Beach just minutes away!

    Clearwater

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