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MONTHLY RENTAL. Introducing our BEAUTIFUL NEWLY RENOVATED LISTING! Nestled within this premier condominium complex, our home offers direct access to the highly acclaimed Siesta Key Beach without the need to cross any streets.Our home away from home is perfect for those seeking a winter retreat or...
Featured review
Chris and Jeannie could not have been more accomodating hosts . The unit was beautiful and well appointed. Residents of the Casarina were extremely friendly. Looking very much forward to returning next...
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Vacation rental close to the # 1 beach in the US - Siesta Key on the Gulf of Mexico (Sarasota)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.Whether you are looking for a perfect destination for your vacation, a romantic...
Featured review
We spent 18 days at the unit. The Unit is beautiful and clean. We enjoyed the location and hope to return next year.
Distance to beach: 800 feet to Siesta Key Beach
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Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master...
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Enjoy the unrestricted views (no sea oats or berm) of the ocean and sunsets from our beach front condo just steps away from the Gulf of America. It is located on Turtle Beach known for its quiet, relaxing, low-key vibe. We have the most unique location on the island, the Sarasota Bay intercoastal waters...
Distance to beach: 250 feet to Siesta Key
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On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis...
Featured review
This was our third stay in this apartment, and everything was perfect as always! Great location, fully equipped with everything you need, and the rental process was easy and hassle-free. Thank you! We would...
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The Condo Bay side water views; 2nd floorPrimary: King BedPrimary bath: tub/shower comboGuest: 2 twins/convert to KingGuest bath: tub/shower comboLiving Room: Sleeper Sofa
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Totally remodeled ground floor unit. This unit is brand new to the rental market and is a rare find. Walk out the rear Lanai door directly to the becach. You can't get any closer to the Gulf of America on Siesta Key. The open floor plan allows Gulf views from the sunroom, master bedroom, living room,...
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Discover your own slice of paradise in this brand new 100% fully renovated 2-bedroom, 2-bathroom villa, with vaulted ceilings and an open floor plan. This villa is located in the vibrant heart of Siesta Key. This charming retreat blends modern amenities with a prime location, ensuring an unforgettable...
Distance to beach: 30 feet to Turtle Beach
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Are you ready to stay directly on the water? The sunsets are beautiful and the Gulf is so refreshing. We look forward to hosting you and your guests!Within just a few feet of the shore, our condominium home features a well equipped kitchen with granite counter tops, luxury vinyl flooring, a leather...
Featured review
Wonderful unit it was so well stocked and all accommodations we very good. we had brought a boat and everything needed was there. great vacation spot . Will come back again.
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Newly remodeled kitchen with stainless appliances. Freshly painted throughout and casual furnishings for your family to enjoy. First floor for quick access to the beach from your lanai door. New drapes at the sliding doors separating the living room and lanai. Renovated master bath and guest bath. The...
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Roomy 2 bedroom, 2 full bath condo in prime Siesta Key location. Comfortably furnished living room, dining area, all linens and fully equipped kitchen included, ceiling fans in all rooms, Flat screen tv in living room with DVD player and a flat screen in the master bedroom. Master bedroom has queen-size...
Featured review
The property was nice and comfortable. The children enjoyed the pool that was close to the unit. Owner promptly responds if we had questions.
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Gertrude's Village House Top location on the island with 3 patios and private gate into world famous Siesta Key Village! Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters...
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Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on the...
Distance to beach: 20 feet to Turtle Beach, Siesta Key
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Beautiful beach inspired decor...Fresh, airy and calm...perfect relaxing unit with all the comforts of home and more to enjoy a fun filled time at the beach!!!!!
Distance to beach: 0.5 miles to Siesta Key Main Beach
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Sweet Siesta Key Condo walking distance to #1 Beach in America! Spacious and Quiet One Bedroom with King Bed, Screened Lanai, Wireless Internet, 2 Flat screen TV’s, covered parking space, full kitchen with amazing water filtration system. Easy Walk right over to Siesta Key Main Beach, and their...
Featured review
Perfect location, situated right in the middle of the village and the south bridge. Restaurants and entertainment either way. It's a 2 min walk to the beach. The condo had everything I needed to make my...
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A211 is gorgeous, newly renovated with brand new kitchen, appliances and cabinets, living room, dining room and bathrooms (all with new walls, ceilings, doors and tiled floors). Also available is a new in-unit large capacity washer and dryer. The kitchen is fully equipped with many of the comforts of...
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Welcome to a bit of heaven!A gorgeous gulf-front vacation awaits you as you come and enjoy this enchanting condo! Located directly on beautiful Turtle Beach in Siesta Key and just steps away outside your door. There is no other resort complex like this that is so close to the beach!As you travel...
Distance to beach: 100 feet to Siesta Key - Across the Street!
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Looking for the perfect beach getaway? Discover your dream vacation at this beautiful 2 bedroom, 2 bath condo only steps away from the world-famous white sands of Siesta Beach! Perfect for couples or families. Only 3/4 mile from Siesta Key Village which boasts great restaurants and shopping. View...
Distance to beach: 0.7 miles to Siesta Key Beach
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**Completely Renovated February 2025** Welcome to island life! Enjoy your own private resort in the heart of the #1 beach in America, Siesta Key!Indulge in the pinnacle of island living at this pristine waterfront home on Siesta Key—a haven where luxury meets natural beauty. In the heart of...
Featured review
5 stars. Wish I could give 10. Beautiful and comfy cozy home, comfortable beds, gorgeous pool, so kid friendly and lovely views from the fire pit. The decor is top notch!! Danielle and Jeb were great-...
Distance to beach: 0.4 miles to Siesta Key Beach
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Location, location, location!! New pool and spa just completed! Waterfall edge from spa to pool and deck jets. New landscaping with additional seating areas near pool and canal. Also, lots of green space to enjoy too!Canal home in heart of the Siesta Key Village, no need for a car! Steps away from...
Featured review
The house was extremely clean and nothing was missing. Loved my stay from beginning to end. Melissa checked in a few times to make sure I was happy. I would stay at this home again. It has raised my bar...
Distance to beach: 0.3 miles to Siesta Key Beach access 10
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*Calendar month rentals only*May - November (7-month lease) - $2000 per month plus utilities December - $3900 per month plus utilities January - $4900 per month plus utilities February, & March- $5900 per month plus utilities April - $4900 per month plus utilities50% deposit upon booking,...
Featured review
I recently had the pleasure of staying for three months in this cozy bungalow on Palm Island in the heart of Siesta Key. Nestled amidst lush vegetation and just a short walk from the beach and Siesta Key...
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Indulge in a luxurious escape at this contemporary Siesta Key home. Featuring 4 bedrooms, 4 full bathrooms, and an elevator, this stunning property offers the perfect blend of comfort and style. Enjoy a private backyard oasis with a swim/spa, and stay connected with included Wi-Fi. This home is ideal...
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Welcome to our newly renovated two bedroom, one bath, ground floor condo on Siesta Key. Located on the IntraCoastal side there is a waterway on the property. Private access to the beach right across the street. Best of both worlds! Heated pool, tiki bar/grill, and fishing pier on the property. Halfway...
Distance to beach: 0.1 miles to Siesta Beach
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Our new unit are truly a site to see. 2 BR / 2 BATH completely remodeled, newly furnished unit with fully equipped kitchen, cable TV, WiFi, and washer/dryer. Enjoy a Resort Style pool area beautifully landscaped with 2 Tiki Bars and plenty of space to work on your tan! Not to mention a grassed area for...
Featured review
Roomy, very clean, very accommodating staff. Pool was super clean and warm. Walk to everything., don't need a rental car!
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Completely remodeled beachfront 11th Floor unit at Crystal Sands. Gulf views from each bedroom and living room south on Crescent beach. (The view in picture #3) is the view from your screened lanai. Elevator down to pool located on the white sands of Crescent Beach. Beach chairs provided by Crystal Sands....
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Discover your Siesta Key oasis! This gorgeous 4-bedroom, 3-bath house boasts a private pool, updated interiors, and a prime location near the beach. Enjoy a fully-equipped kitchen, high-speed internet, and a spacious layout that comfortably sleeps 10. Relax on the covered lanai, soak up the Florida sun,...
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Discover your perfect getaway in this newly renovated 1150sq ft Villa! 2 bedroom 2 bathroom with updated furnishings, fully equipped kitchen, and private lanai perfect for enjoying the sunshine.Stand alone with Covered Carport. Great Location with Crescent Beach a short walk away (less than 6 min)....
Distance to beach: 200 yards to Siesta Key Crescent Beach
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SIESTA SUMMER SAVINGS! RECEIVE 10% OFF YOUR SUMMER STAY BETWEEN 5/30/26 AND 8/29/26 WHEN BOOKING DIRECTLY ONLINE AT THE ANCHORAGE YACHT & TENNIS CLUB IN-HOUSE RENTAL PROGRAM WEBSITEWe invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal...
Featured review
We stayed at the Anchorage in unit 305. It faces the city and the inner coastal lagoon. We were treated to a dolphin show one evening when they entered the lagoon searching for food!! This location...
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4th floor Bayside 2 bedroom, 2 bath condo located in the Capri Building at Excelsior. Complex has two pools (one beachside/one bayside) with hot tub, 3 lighted tennis/pickleball courts, outdoor BBQ/picnic area. Unit has washer/dryer, WIFI, 2 TVs and DVD. No pets. No trucks/trailers or motorcycles allowed...
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Beautiful Crescent 2 bedroom penthouse with partial beach views, large balcony overlooking pool area in the center of the complex. Additional beach front pool also offered. Equipped with hardwood floors, large kitchen and laundry. 3 TVs, WIFI. Complex offers fitness center, 2 parking spaces and located...
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3 Bedroom/ 3 Bath Beachfront Townhome in Siesta Village, offering beautiful sunsets from your 2 balconies. Note that the beach directly in front of the property is private and may not allow access. Public beach access is always available just a few steps away. Go a block behind the unit to all the restaurants...
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Come relax in this quiet bayside complex that is surrounded by whispering oaks. 2nd floor unit is a 2 bedroom/2 bath remodeled unit. Complex offers tennis courts, community pool and pier for fishing. Unit has tile in main traffic areas with carpet in bedrooms. Leather sofa, open kitchen wit granite countertops....
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Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this remodeled home delivers on design, location and lifestyle. Featuring four bedrooms, two-and-one-half baths and washer & dryer. Please note that the garage and boat dock is not available but there is plenty of parking in the...
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3rd floor unit in the clubhouses located on the beachside of Palm Bay Club, which is steps from the beach. Custom cabinets, granite counters, stainless steel kitchen appliances, screened lanai, 3 LCD TV's, stackable washer/ dryer in unit. WIFI. Complex offers elevators, 2 pools (1 beachside, 1 bayside),...
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Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award-winning white sand beaches await. Beautiful first floor, 1 bedroom w/den in Bayside community of Bay Oaks. 3 TV's. Sleeps 4 (King in master bedroom, den has a twin bed and living room has a sleeper sofa. Complex offers swimming...
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Welcome to Siesta Key Paradise! * available for winter/spring 2026* Your home away from home. Located in a prime spot on the quiet end of Siesta Key, this recently updated two-bedroom, two-bathroom is a great getaway.The condo is located at Mariners Inlet, which is an 8-unit complex located directly...
Distance to beach: 0.5 miles to Siesta Key Main Beach
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Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo,...
Featured review
Thank you again, Barbara and Angelo, for providing your vacation home for our annual trip to Siesta Key. November is our favorite month there, with perfect temperatures and a tranquil setting. The property...
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This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry...
Featured review
The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed...
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Breathtaking Direct Oceanfront Condo – Wake up to panoramic views stretching the entire length of Siesta Key Beach in this elegantly appointed 9th-floor oceanfront retreat, perfectly located near the Stickney Point Bridge Village shops and restaurants and a marina. This residence offers designer...
Featured review
Location and condition and furnishings of condo are the best, the only suggestion we have (and it's not a deal breaker ) is a recliner or two would be great.
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Contemporary 3 Bedroom 3 Bath Luxury townhome. Beach views from the 3rd bedroom on top floor with full bath and bonus room and murphy bed. Master suite with tub and walkin shower, Gourmet kichen, leather furniture, balcony with partial views of the Gulf from the 3rd floor balcony. Laundry in unit, 2 car...
Distance to beach: 0.5 miles to Siesta Beach access 7
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*Calendar month rentals only* 2026 Rates May-November (7-month lease) - $3000 per month plus utilities December - $6900 per month plus utilities January $7900 per month plus utilities February & March - $9800 per month plus utilities April - $7900 per month plus utilities50% deposit upon...
Featured review
I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta...
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Escape to paradise in this stunning newly renovated beachfront condo on Siesta Key! Enjoy breathtaking ocean views from the living room and both bedrooms. Relax on the large lanai, or get cozy in the large living room furnished with comfortable leather seating. This popular unit offers TVs in each bedroom...
Featured review
Room was very nice and clean, kitchen well stocked with washer and dryer. Best thing we could open the door and you were right on the beach. So convenient for the kids and adults to run up to the condo...
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This 3400 sq ft., 5 Bedroom 3.5 Bath, Townhome Offers, Private heated pool- **please keep in mind the pool is refreshing, but has limited space for larger parties. Many balconies overlooking the pool. Beautiful custom kitchen, with Granite and Stainless. It has a patio and 2 car garage. 2nd Floor is Living...
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Second floor, 2 bedroom/2.5 bathroom townhome located in the quiet complex of Bay Oaks. Unit is nicely furnished with plenty of space. Tile flooring in kitchen, dining room and living room. 2 TVs with washer/dryer inside unit. 2 screened lanai's, small balcony and full kitchen. WIFI in unit. Complex...
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Enjoy spectacular views of the Gulf from all levels of this freshly remodeled, coastal contemporary townhouse featuring a master Bedroom with a den and luxurious bathrooms. The beach is just a block from Siesta Village offering restaurants, shopping and nightlife. This three-story unit features a convenient...
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This 2nd floor luxury beachfront condo is updated with designer furniture and furnishings. Fully restocked kitchen with granite countertops and stainless steel appliances. 3 bedroom/3 bath direct beach and pool views from either of the two balconies. Access to small workout room. Washer/Dryer in unit...
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Come relax in this quiet bayside complex surrounded by whispering oaks. 2 bedroom/2 bath unit is locate on the 3rd floor. Complex offers heated pool (Nov. through April), tennis, full laundry facility at complex, community room and small pier for fishing. Wood floors throughout with leather furnishings...
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Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. Completely remodeled, 1 bedroom/1 bath, 1st floor condo with private screened lanai with new pergo floors and new kitchen. Washer/dryer in unit located just one block from the shops and restaurants...
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Your home away from home on Siesta Key with 2 bedrooms 100 steps to the beach. This fabulous condo features a comfortable king bed, a full bed, and a twin bed, perfect for families or friends traveling together. Guests enjoy two bathrooms, each equipped with a refreshing shower and a hair dryer for convenience....
Featured review
A truly perfect condo on the beach with fantastic views of Crescent Beach and Siesta Key Beach. This ocean view unit, also overlooks the largest pool of three available on this well landscaped, large gated...
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Experience refined coastal living in this newly refurnished 2BR/2.5BA condo, where luxury meets relaxed island charm. Enjoy elegant décor, 800-thread-count linens, and a gourmet kitchen with granite and stainless steel. Sip coffee on the balcony with a Gulf breeze, unwind by two pools, or stroll...
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