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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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Second and third floor Bayfront townhome. Living area on second floor and interior stairs lead to bedrooms on third floor. Top of the line unit, offering travertine floors, new kitchen & baths, leather furnishings, 1/2 bath on the 2nd floor and 2 baths on the 3rd floor. Unit offers highspeed internet...
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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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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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Experience luxurious living in one of the largest units on Siesta at this stunning 2 bedroom, 2 bathroom condo. This immaculate condo features porcelain tile flooring in the living areas, brand new plush carpeting in both bedroom, and beautiful crown molding. The kitchen is a chef's dream, with custom...
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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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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...
Distance to beach: 0.3 miles to Siesta Key Beach
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*Calendar month rentals only***Last minute availability - JANUARY 2026 - $5900 per month plus utilities**December - $6900 per month plus utilities January - $7900 per month plus utilities February - $12,000 per month plus utilities March- $9800 per month plus utilities April and May - $7900...
Featured review
Choose this home for its fantastic location, hosts and amenities - easy walk to the beach or downtown Siesta Key, but feels miles away from the crowds in its tropical setting.The home was perfect for...
Distance to beach: 4 miles to Siesta Key Beach
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Create memories with friends and family at this unique, and spacious property only 10 minutes from Siesta Key Beach. It is perfect for large groups or reunions as this house includes separate living spaces and has a total of 13 beds. Right behind the main house, you will find a fun area to relax, play...
Featured review
This is a wonderful 5 plus star accommodation! The location is perfect, so convenient to the beach and so many things to do. The house is stocked with everything you need and more. Michael is an excellent...
Distance to beach: 850 feet to Crescent Beach
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Direct-with-Owner Rental Discounts: Midnight Cove #532 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed...
Featured review
This 2 bedroom ground floor condo was comfortable, clean, stylish and centrally located. It was fully stocked eith cleaning and cooking supplies as well as hairdryer and iron. We had a great time and...
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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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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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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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Available October 15, 2026 through March 15, 2027. The ideal rental is the full seasonal period, although other stays of two months or longer may be considered.Spend the winter where everything is within walking distance.Welcome to your home away from home in Villa Navarra, an intimate 16-unit...
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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White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay.MESSAGE ME FOR LINK TO THE BOOKING WEBSITE AND...
Featured review
Had a great time at White Sands #308. Close to the beach and a very nice pool with grills! Super easy to get around with the trolly and “frog hop” so you don’t have to drive. Highly recommend.
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Very nice 4 Bedroom home on a canal just about 5 blocks to Siesta Village. offering: 1 car garage, Duet washer/dryer, Private pool, decorated with a Island flare. Tile throughout with granite and stainless steel kitchen appliances. Beautiful setting pool and patio overlooking canal with boat dock. (Boat...
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Escape to paradise at this peaceful studio on Siesta Key! This ground-floor unit in the Casa Mar complex offers a prime location near the beach and pools. Featuring a queen Murphy bed, a twin bed, a covered parking space and WIFI. Guests have access to the complex's pools, tennis courts, shuffleboard...
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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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Escape to paradise in this stunning 2-bedroom home on Siesta Key! Enjoy the Florida sunshine by the private pool or relax in the enclosed lanai. This beautifully updated home across from the canal features a brand-new kitchen and bathrooms, comfortably accommodating four guests with a king and queen bed....
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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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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...
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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...
Featured review
We were due to stay for 2 weeks from 26th sep unfortunately due to hurricane helene we weren't able to stay .siesta rentals returned all our sad but we will come ahain
Distance to beach: 250 feet to Crescent Beach
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Direct-with-Owner Rentals: Siesta Breakers #603 offers "All-In Price" 10% to 25% Discounted Rental Rates from $2,095 to $3,921 /Wk Depending on the Season and payment method ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $366 to $855 /Wk from...
Featured review
The condo was very clean and comfortable. Beautiful view from the lanai. Great location, walking distance to many restaurants and ice cream parlors!
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Second floor, 2 bedroom/2.5 bath townhome located in the quiet complex of Bay Oaks. Unit nicely furnished and offers tile flooring kitchen, dining room and living room, 2 TVs, washer/dryer inside, 2 screened lanai's. Small balcony and full kitchen with wireless high-speed internet. Complex offers...
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Discover your perfect Siesta Key getaway at Commonwealth Place! This charming 3-bedroom house offers a luxurious stay with a private pool and is located near the ocean. Enjoy the Florida sunshine and relax in a home equipped with modern amenities like a full kitchen, air conditioning, and Wi-Fi. With...
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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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You have access to a deeded walkway from your condo to the beach while living directly on the intercoastal waterway with a great view. The intercoastal waterway, with its parade of all types of boats and dolphins swimming by, is visible from practically every room. This 2nd floor, 1 Bedroom/1 Bath...
Featured review
Wonderful location for boat watching and easy access to the beach. Owners are lovely and super easy to work with.
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Breathtaking gulf front 2 bedroom/2 bath unit in beautiful Crystal Sands complex. Granite countertops, tile floors in living room, kitchen and bath. Wood flooring in the bedrooms. Leather furniture, 3 TVs, washer/dryer in unit, WIFI. No pets. No smoking. Sleeps 6 (1 king, 2 queens). 2-week minimum. Check...
Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach
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*Calendar month rentals only*May-November (7-month lease) - $3000 per month plus utilities December - $6900 per month plus utilities January, February, March, & April - $9800 per month plus utilities50% deposit upon booking, balance 90 prior for monthly rentals. Check the calendar for...
Featured review
It's all about The Lily Patch on Palm Island in the village of Siesta Key!!! We've love it so much that we've signed up again for 2021 (Winter #3) and sent in a donation to the neighborhood HOA this time. Bring...
Distance to beach: 0.3 miles to Siesta Key Beach
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Renovated 2BR (one queen size & 2 single beds) 2 Bathrooms 2nd floor condo and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paved stones drive and covered parking, newly installed luxury wood-like flooring a comfortable...
Featured review
We spent a month at this beautiful condo. It was very well equipped with everything we needed. Lovely warm pool and such a short walk to Siesta Key Beach. Thank you Lynette (the owner) for making this...
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Escape to paradise in this beautifully updated apartment on Siesta Key! Enjoy direct beach access, sparkling pools, and tennis courts. This 2-bedroom, 2-bathroom apartment offers a perfect blend of comfort and convenience, with a fully equipped kitchen, private balcony, and free parking. Explore nearby...
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Quaint 1 bedroom bungalow with Murphy bed that folds into the wall during the day providing additional living space. Living room w/leather furniture, French doors open to a private brick patio. 2 Smart TVs (43-inch in living room and 32-nch in bedroom). Kitchen offers a mini convection oven w/ burners...
Featured review
Walkable to Sneaki Teki , 7 eleven and a 5 minute walk to the beach. They offered beach chairs and umbrellas. Great responsive hosts.
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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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Escape to this charming 3-bedroom house on Siesta Key, offering a private pool and a 2-car garage just a short distance from the beach. Enjoy amenities like a fully-equipped kitchen and a charcoal grill, which is perfect for family gatherings. With multiple TVs and high-speed internet, relaxation is guaranteed....
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Welcome to our exquisite three-bedroom, two and a half-bath Siesta Key home, where the magic of the tropics meets unparalleled comfort and convenience! Imagine waking up to the vibrant spectacle of parrots gracefully flitting overhead, a delightful start to your vacation amidst our lush, tropical backyard...
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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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Escape to paradise in this stunning two bedroom apartment located just steps away from the pristine white sands of Siesta Key Beach. This modern coastal retreat is designed for comfort and convenience, featuring a spacious layout with a king bed, a queen bed, and a full bed, making it the perfect choice...
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* Please Note: The exact home location is not shown on the map. Message us for the exact address*Siesta Key Canal Oasis – Walk to Village & Beach!This private single-family home offers the perfect Siesta Key experience — located just a 1-minute walk to Siesta Key Village and a...
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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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Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. Gorgeous Gulf front 2 bedroom/2 bath unit at Crystal Sands complex. Tile floors through kitchen, baths and living room. 3 TVs with washer/dryer in unit. Screened-in lanai off all rooms with direct access....
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This lovely penthouse condo is in one of Siesta Key's luxurious complexes. The Crescent offers luxury living at its finest. Bask in the spectacular view of the world famous Crescent beach on Siesta Key from this 3 bedroom/3 bath beachfront condominium with open-air balcony, living room, kitchen and...
Distance to beach: 0.7 miles to Siesta Key
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House of Siesta: our home by the coast. We’re opening our doors not to a regular rental but to our own home, created with love so guests can feel truly at home too. Just 0.7 miles from the #1 beach in the USA and minutes from Siesta Village, it’s spacious, welcoming, and perfect for two families...
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Welcome to Casa De Mayo — your private waterfront retreat in the Village of Siesta Key within walking distance to the beach. Perfectly situated just a stroll from Siesta Village and the world-famous powder-soft sands of Siesta Beach, this stunning home offers the best of both worlds: vibrant island...
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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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...
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