Clearwater Vacation Rentals
View Top Destination Searches
Rental Type
Search Radius
Surrounding Areas

Click the pins to select or deselect an area.

Condo Complex
Apply Filter ×

Sand Key Vacation Rentals

  • Guaranteed Bookings with 100% Protection

  • Easy Changes & Cancellation

  • 24/7 Emergency Support

Todd B. VaycayHero Guest

"Glad I discovered VaycayHero. Super easy to use with lots of inventory. Will be using more in the future."

Sort By

694 rentals are available

  • Your ultimate vacation begins with this incredible beach house. This deluxe 5 bedroom 4.5 bathroom house is a splendidly designed 3-level house with all the comforts of home and all the extras you’d want for your ideal vacation. This 5,000+ square foot beach home is ready to welcome your family and friends for an unforgettable vacation!

    Our Beachcomber’s home features comfortable furniture, theater room, game room, over 5000 Sq ft and much more! You will be impressed from the moment you open the front door!

    The ground level features a large area for entertaining, a Game Room and a Theater. The Game Room includes a Ping-Pong table, large flat screen TV, seating areas and a popcorn machine. The Theater room is an entertainment room is perfect for guests of all ages! It seats 5 guests comfortable. This room is set up to be the perfect cinematic experience.

    The surround sound system and projector create the perfect home cinema experience. The first level also features a full bathroom. The ground level features easy access to the pool area where you will find comfortable lounge areas and a fishing deck.  The second level features a large formal living room, dining area, fully equipped kitchen, laundry area, 3 bedrooms, full bathroom and a powder room. There is a bbq grill on the second level balcony.

    The formal living room features sofas designed for comfort – fit to entertain guests or curl up with a book away from the activities and entertainment around the house. Our vacation home has a fully equipped kitchen with all the amenities needed to cook a special meal. Kitchen bar seats 6 comfortably in addition to our dining table seating 6 guests. This fully equipped kitchen includes everything you could want on vacation: fridge with icemaker, microwave, coffee machine, blender, glassware, cookware, toaster and more! Our kitchen has it all!

    The third level features 2 master bedroom suites, each bedroom with a private bathroom, large walk in closet and a private balcony.  The bedroom layout is as follows: First bedroom in the second level features a Queen size bed, second bedroom in the second level features a Queen size bed and access to a balcony, third bedroom in the second level features a pull out sofa and access to a balcony.

    The second level has a full bathroom by the bedrooms and a powder room by the kitchen area. Fourth bedroom in the third level is a master suite with a King size bed. This master suite boasts a large walk in closet, private bathroom and a private balcony. The fifth bedroom in the third level is also a master suite with a Queen size bed featuring a large private bathroom, walk in closet and a private balcony. Our rental home sleeps 10 -12 guests comfortably.

    All rooms throughout are beautifully decorated; we've taken care to make every bedroom welcoming, calm, and ultra-comfortable. Each bedroom is spacious and has easy access to the balconies for spectacular views of the water.  You can enjoy the water views from all 3 levels of this gorgeous home. Each balcony features comfortable seating areas.

    This luxurious vacation home features balconies on the second and third level. There is a staircase that leads you to the second level balcony from the pool area. Enjoy the tropical breezes from any of the balconies.

    Enjoy swimming, playing, or relaxing around your own private pool and hot tub. Seating around the pool includes chairs and chaise-lounges.  The outside area of the property has a small deck that can be used for fishing.

    Amenities include Cable TV, DVD Player, Central Air, Air Conditioning, Ceiling Fans, Linens, Washer & Dryer, High Speed Internet, Views of the water, Full Kitchen, Refrigerator, Coffee Maker, Ice Maker, Microwave, Toaster, Views of the water, Balcony, BBQ Grill, Hot Tub, Private Pool, BBQ Area.

    Bed Configuration: Bedroom 1: Queen | Bedroom 2: Queen | Bedroom 3: Pull-Out Sofa| Bedroom 4: King | Bedroom 5: Queen.

    Square Footage: 5100 Square Feet.

    Location Distance: Busch Gardens - 35 minutes drive | Adventure Island - 35 minutes drive | The Florida Aquarium - 40 minutes drive | Tarpon Springs - 45 minutes drive | TPA Airport - 40 minutes drive | St. Pete Airport - 20 minutes drive | Johns Pass - 10 minutes drive | St. Petersburg - 30 minutes drive.

    It was awesome. The house was great. There was everything at this house you would ever need.We had 9 of us stay there and there was room for more. We love the Clearwater Beach area and will continue to stay in the area. The lady that got us started at the house was great to work with. Pool was great, the view from there was also. Dolphins with in 10 feet of the dock everyday.

    Clearwater Beach 0.84 miles
  • This exquisite condo features 3 bedrooms and 2 bathrooms, a fully equipped kitchen, open dining room and living room. There is a large deck where you can sit and enjoy the partial intercoastal view while enjoying a cup of coffee or reading a book. Our large living area is open and it features comfortable furnishings seating a total of 8 guests, flat screen TV, wet bar and it opens up to our dining area which seats 6 guests comfortable. The fully equipped kitchen features granite counter-tops, a large island with additional seating, stainless steel appliances and everything you will need for a family meal.

    Our Gulfside Luxury Condo is professionally decorated with upscale furnishings. Master bedroom is large and boasts a King-size bed, Second bedroom boasts a King size bed and third bedroom features two full-size beds accommodating 8 guests comfortably. All bedrooms feature comfortable pillows and sheets and flat screen TVs. There are two bathrooms, which are completely upgraded featuring walk in showers. Bathrooms are equipped with bath towels and adequately sized vanities for beautification and grooming. This property defines perfection and total relaxation.

    This property is complete with all the luxuries and more one would expect, providing an ideal location for a fun relaxing wonderful get a way! This lovely condo is located on Mandalay Ave with easy access to the beach, just across the street. Pier 60 is located less than a minute walk from this property. This is the best location you can get in Clearwater Beach. Our rental condo features WIFI service for your entertainment enjoyment. We have washer and dryer at your service as well.

    This gorgeous property is located on the second floor with two private entrances. A unique feature of this high-end condo is that there are only two units in the building limiting foot traffic. A stay at our Gulfside Luxury Condo will leave one relaxed and rejuvenated and planning ahead on how soon you can return.

    Amenities include Wireless Internet (Wi-fi), Air Con, BBQ, Big Screen TV, CD Player, DVD Player, Grill, Hair Dryer, TV in Every Bedroom, Paved Parking, Full Kitchen, Laundry In Unit, Microwave, Dishwasher.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: 2 Fulls.

    Square Footage: 2000 Square Feet.

    We were pleased with the location and spacious living space and kitchen. One king bedroom was large while the other had no closet or window. We made do. Also, the kitchen had great appliances but was in need of more serving utensils and cookware and bakeware. There is no large pot for a shrimp boil. Outdoor space was under construction but will probably be very nice once finished. Also, need wine glasses.

    Clearwater Beach 1.35 miles
  • 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 1.89 miles
  • This magnificent, designer-decorated home is one of a kind. Luxury ~ Beauty ~ Comfort ~ All encompassed into our 4 bedroom villa in Clearwater Beach! Our rental home is in the ideal location of Clearwater Beach- so close to shops, the Pier, Restaurants, Water Sports and much more. Our White Sands Villa is a dream home to vacation in.

    Step outside the front door and start enjoying playtime on the beach. The beach is located just 30 seconds away. With comfortable sleeping accommodations for 14, this 4 bedroom exquisite home is perfect for a large family getaway. You will enjoy all aspects of this stunning home from the dipping pool to the breathtaking Gulf views. With lush tropical settings and beach access only steps away, this home will be a vacation paradise to remember.

    The first level consists of a large living and dining area and a fully equipped kitchen. The Kitchen is open to the entire room and tastefully appointed with granite counter-tops. It opens into the living area and dining area. The kitchen is equipped with stainless steel refrigerator, oven, microwave, ice maker, coffee maker and dishwasher. The dining area is perfect for gathering at breakfast or enjoying a home cooked meal. Our spacious living room has comfortable furnishings which includes a 70 inch flat screen television and a pull out sofa.

    The first bedroom with a King-size bed and a full bathroom is located on the first level. Laundry room is included on this floor. The first level also consists of a beautiful covered porch with an outdoor dining table and a gas bbq grill – all private to our White Sands House. The second level has a second living area with a pull out couch and a common area for everyone to enjoy. The second bedroom with a King-size bed and a full bathroom is located on this level andtThere is a large balcony where you can enjoy a southern view of the gulf.

    The third level has the Master Suite with a King-size bed, a trundle bed and the master bathroom. Master bathroom is one of a kind with a tub and a walk in shower. This level has a balcony where you can also enjoy gulf views. The third level also has the fourth bedroom with a set of bunk beds perfect for the kids. The fourth level is an open deck where you can enjoy the gulf views and fireworks. This deck is private to this home.

    The house is laid out perfect, on 4 floors, with each bedroom on a separate floor and each floor has its own central air conditioning unit making it ideal for family groups as it offers Plenty of privacy so everyone can have their own area to get away.

    This vacation rental has over 2850 sq feet and it gives you all the comforts of home plus some extras. Our beautiful shared pool is perfect for unwinding after a day at the beach. Our vacation property is in close proximity to the shopping, entertainment, Pier 60 and much more.

    Please note a total of 3 parking spots is available for this unit only.

    Amenities include Communal Pool, Water View,Wireless Internet (Wi-fi),
    Air Con, BBQ, Big Screen TV, CD Player, DVD Player, Grill, Hair Dryer, TV in Every Bedroom, Beach On Site, Full Kitchen, Laundry In Unit, Microwave, Sea View & Dishwasher.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: King with Trundle | Bedroom 4: Bunk | Living Area: Sleeper Sofa.

    Square Footage: 2850 Square Feet.

    Clearwater Beach 1.89 miles
  • Our Sea Turtle Suite is an exquisite rental in a fantastic location and is sure to keep you coming back time after time! This suite is located on the second floor of the property.

    Our Sea Turtle rental consists of one bedroom with a private bathroom, living area with a pull out couch, completely kitchen and dining area.
    Sleeping a total of 4 guests.

    This bedroom features a King-size bed with a private bathroom, and a flat screen television with a DVD player. This cute vacation rental has a balcony with a partial beach view. Perfect location! In the heart of Clearwater Beach just steps from restaurants, bars, entertainment and shops. Please note a 1 parking spot is available for this unit only.

    Amenities include Communal Pool, Water View, Wireless Internet (Wi-fi), Air Con, BBQ, Big Screen TV, CD Player, DVD Player, Grill, Hair Dryer, Beach On Site, Full Kitchen, Laundry On Site, Microwave & Sea View.

    Bed Configuration: Bedroom 1: King | Living Area: Sleeper Sofa.

    Clearwater Beach 1.89 miles
  • 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 1.35 miles
  • Our Driftwood Beach Cottage is the ultimate location to experience both comfort and luxury when visiting Clearwater Beach. Melt away into the beach lifestyle the moment you step inside this beautifully remodeled, newly furnished, 2 bedroom, 1 bath beach cottage. Step from beach style decor into white, surgery sands mere paces away. Located in desirable North Clearwater Beach, make the Driftwood rental your beach paradise retreat.

    This is a very large two bedroom, one bath cottage that sleeps 6 comfortably. The first bedroom has a Queen-size bed and the second bedroom has a Queen-size bed. There is a pull out sofa in the living area, which totals accommodations for 6 guests total. The living area features upscale plush furniture and a Large screen TVs with cozy sofas.

    Our beach rental includes the finest finishes you could ever find in a vacation rental. The spacious and beautiful gourmet kitchen if completely equipped for family meals. The kitchen has a partial beach view. Shared amenities include the courtyard and the infinity splash pool. For your convenience, this suite is located on the ground floor with no stairs.The beach is located just 30 seconds away.

    Please note a 1 parking spot is available for this unit only.

    Amenities include Communal Pool, Wireless Internet (Wi-fi), Air Con, BBQ, Big Screen TV, DVD Player, Grill, Hair Dryer, Sofa Bed, Beach On Site, Full Kitchen, Laundry On Site & Microwave.

    Bed Configuration: Bedroom 1: Queen | Bedroom 2: Queen | Living Area: Sleeper Sofa.

    Dirty furniture.. Fabric needed cleaning. A/C was not very good. We wanted to open windows at times, but didn't because we were afraid that the inside temp would not cool down. Hard/stiff mattresses. Could only access internet outside the cottage . No inside internet access signal... Convenient laundry. Appreciate high chair and iron. Good beach access, no direct view, , but loved the beach. Convenient to restaurants, beach shopping and entertainment . We felt safe. Owner onsite.

    Clearwater Beach 1.89 miles
  • This is a 2 bedroom, 2 bathroom condo that sleeps up to 4. There's plenty of guest parking, and you'll love entertaining from your spacious kitchen and living/dining room combo. A great balcony for enjoying those famous Gulf Coast sunsets.

    Amenities include Full Kitchen, Refrigerator, Coffee Maker, Ice Maker, Microwave, Toaster, Cookware, Blender, Dishwasher, Range, large heated pool & spa, large gulf front balcony.

    Location Distance: Area FitnessCenter: 15 minutes | Nearby Hospitals: 15 minutes | Grocery-Publix: 10 minutes | Grocery-Winn Dixie: 15 minutes | Ellenton Outlet Mall: 1 hour | Movie Theatres: 20 minutes | Golf Courses-Over 40: in area | WalMart Super Center: 35 minutes | Convenience Store: 5 minutes | Largo Mall: 20 minutes | Seminole Mall: 20 minutes | Tyrone Mall: 35 minutes | Countryside Mall: 45 minutes | International Plaza Tampa: 45 minutes | Westshore Plaza Tampa: 45 minutes | Salvador Dali Museum: 45 minutes | Ruth Echerd Hall: 30 minutes | St.Pete Museum/Fine Art: 35 minutes | Great Expect. Kids Museum: 35 minutes | St.Pete Museum of History: 40 minutes | Fla Holocaust Museum: 35 minutes | Mahaffey Theater: 35 minutes | Fla Botanical Gardens: 10 minutes |Heritage Village: 10 minutes | Bush Gardens: 1 hour | Sea World: 1 hour 45 minutes | Disney World: 2 hours | Universal Studios: 2 hours | Lowry Park Zoo: 45 minutes | Florida Aquarium: 45 minutes | Clearwater Marine Aquarium: 15 minutes | Ft DeSoto State Park: 45 minutes | John's Pass Village: 15 minutes | Deep Sea/Charter Fishing: 15 minutes | Parasailing: 15 minutes | Waverunner Rental: 15 minutes | Boat Rental: 15 minutes | Marinas: 10-15 minutes.

    Lorri Marshall made this experience very enjoyable. She was always available to help us with any questions. The condo was just what we wanted and we have already booked for next year.

    Clearwater Beach 0.45 miles
  • Beautifully decorated. The living area has a vaulted ceiling which peaks at 9ft, and spreads through out the condo. There are many large windows letting light in and allowing you to see the scenery. From the living area you can enjoy a view of the intra-coastal waterway.

    The kitchen features granite counter-tops and high cabinets with stainless steel appliances such as a convection oven, built-in microwave and side by side fridge with ice and water dispenser in the door.You'll never want to leave!

    Clearwater 0.73 miles
  • Beautifully decorated excellent ambiance for any group of travelers and is well appointed with warm and inviting furnishings and artworks. This incredible Dockside unit will make you feel like a permanent resident in Clearwater Beach. Off of the second bedroom, there is a private balcony with 4 chairs, a table and beautiful city skyline and Gulf of Mexico views. The beautiful living room furnishings include a sleeper sofa, a great entertainment center with a large flat screen TV, a newer tan couch, a nice leather side chair and room for  everyone.

    Clearwater 0.73 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 1.58 miles
  • Beautifully This unit offers intra-coastal views from the windows in the front of the condo and a shared balcony facing the bay, boasting the perfect location to sit and read or watch the boats and dolphins pass on their daily journeys. The unit is newly refurbished with granite counter tops and a great layout for family or friends sharing accommodations.

    Clearwater 0.73 miles
  • Enjoy this newly furnished beach rental located on the island of world renowned Clearwater Beach. Just a short walk to the sand, this 3 bedroom, 2.5 bath town home is beautifully decorated with large expansive and comfortable living areas. The town home sleeps (maximum) eight people and is cozy and comfortable. This is THE location to be on Clearwater Beach.

    Clearwater 1.55 miles
  • Enjoy this nicely furnished beach rental located on the island of world renowned Clearwater Beach. Just a short walk to the sand, This 3 bedroom, 2.5 bath town home is beautifully decorated with large expansive and comfortable living areas. The town home sleeps (maximum) eight people and is cozy and comfortable. This is THE location to be on Clearwater Beach.

    Clearwater 1.55 miles
  • Our Beach Escape Beach House is a beautiful beach townhome offering spacious and inviting accommodations for that long awaited vacation! This home has been custom-decorated and furnished with unique and beautiful accents and art. can enjoy the sun, surf and soft sand and create memories that will last a lifetime!

    Clearwater 1.92 miles

See Our Other Locations

See All Locations
View Your Password By signing up, I agree to VaycayHero's Terms of Service & agree to join our mailing list for special offers and travel tips.

Forgot Password?


Our concierge specialist is standing by to help you with your booking.
Call 888-733-2964 .