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Distance to beach: 0.5 miles to Siesta Key Beach
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*Calendar month rentals only* 2026 May - November (seven-month lease) - $2000 per month plus utilities December - $3900 per month plus utilities January - $5900 per month plus utilities February & March - $6900 per month plus utilities April - $4900 per month plus utilities50% deposit upon...
Featured review
This studio was perfect for our 4 week stay in Siesta Key! The neighborhood is beautiful and quiet-and everyone we met was so friendly-to us and to our dog! Every day we walked into the Village-where...
Distance to beach: 0.3 miles to Siesta Key Beach access 10
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About this property
*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...
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...
Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach
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About this property
*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: 0.4 miles to Beach access 10 of Siesta Beach
Key Amenities
About this property
*Calendar month rentals only*May-November (7 month lease) - $3000 per month plus utilities and tax. November & December - $6900 per month plus utilities January, February, March, & April - $9800 per month plus utilities50% deposit upon booking, balance 90 days prior for monthly rentals. Check...
Featured review
I loved my two months at Blue Lagoon. It has a great location, near the beach and the village. Palm Island is a great neighborhood, a secluded enclave within Siesta Key. I got to know a lot of my neighbors...
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Distance to beach: 0.5 miles to Siesta Beach access 7
Key Amenities
About this property
*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...
Distance to beach: 0.7 miles to Turtle Beach
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About this property
Welcome to Bayside Haven at the Pointe, your perfect getaway nestled along the serene shores of Sarasota Bay. This charming vacation rental features two spacious bedrooms and two full bathrooms, ensuring ample comfort and privacy for you and your guests.The fully equipped kitchen is perfect for preparing...
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Escape to the island and experience the #1 Beach in the USA! This updated end unit condo offers a spacious floor plan with a pool and is just two blocks from the award-winning white sand beaches. Enjoy convenient access to shopping and the shared laundry facilities. Assigned parking. No smoking. No pets....
Distance to beach: 0.3 miles to Siesta
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Enjoy resort amenities at the Harbor Towers tennis and Yacht club in Siesta key. The building has completed a $13 million dollar structural and cosmetic renovation and is a beautiful building highlighting Siesta key and Midnight Pass. This condo offers the option to play tennis, swim at the pool exercise...
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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Wake up to breathtaking views of the award-winning Siesta Key Beach from every room in this stunning, updated two-bedroom, two-bath condo. Designed for relaxation, this bright and airy retreat features an open floor plan, neutral tile, and an abundance of natural light. Step onto the screened-in lanai...
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The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living....
Featured review
Siesta Key was very beautiful and a great place to visit. The accommodations were very nice, clean and comfortable. We hope to visit this area again next year.
Distance to beach: 0.1 miles to Crescent Beach on Siesta Key
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This 2nd floor, completely renovated 2 bedroom, 2 full bath condo in Siesta Harbor with private beach access and overlooking its own private harbor is the perfect getaway to the #1 beach on Siesta Key in Sarasota, Florida. This unit is located near the community pool and hot tub along with guest grilling...
Featured review
Very much enjoyed our travel South to escape Northern Winter Vortex. Siesta Harbor newly decorated Unit was nicely located, walking distance to nearby restaurants, shops and market. Especially enjoyed safe...
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Escape to paradise in this updated 2 bedroom/2 bath villa at Polynesian Gardens on Siesta Key! Featuring an updated kitchen, tile floors and washer/dryer in unit. Enjoy three TVs and a private patio accessible from the master bedroom. Relax by the community pool and stay connected with WIFI. Beach access...
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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...
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...
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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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Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. 4th floor unit is 1 bedroom, 1 bath on the corner with a washer/dryer. Complex offers community pool, tennis and community room. 1 assigned covered parking spot. Unit has 2 TVs, high-speed internet....
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Beautiful ground floor 1 bedroom/1 bath unit with screened porch at White Sands located just a few blocks from Siesta Key public beach. Community coin-operated laundry right outside door. Covered parking with community pool and clubhouse. Unit has beach chairs, umbrella and beach wagon. 2 TVs with WIFI....
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Escape to paradise on Siesta Key! This charming 2 bedroom/2 bath condo is just steps from the award-winning white sands of Siesta Key beach. Enclosed patio. Enjoy the refreshing pool and amenities like tennis and grilling. WIFI. No pets. Sleeps 4 (1 King, 2 Twins). 2-week minimum. Check in: 15:00 - 23:59 Check...
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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.
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Our little piece of paradise is a one bedroom condominium ideal for couples or young families. We are located at 73 Avenida Messina in unit #7 on the ground floor of the Gulf Holiday Apartments. We are 300 ft. from the Gulf of Mexico and about a five minute walk from the village - known for its shops,...
Featured review
Great place, updated and clean with everything you need! Beach supplies came in handy for trips to the beach. The pool was a great place to go at the end of the day! The office personal were very pleasant...
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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.
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...
Distance to beach: 0.3 miles to Crescent Beach on Siesta Key
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Siesta Key Condo - Siesta Key ParadiseLooking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii.Enjoy great views from our lanai watching boats, yachts, and wildlife on the Intracoastal...
Featured review
You wouldn’t think a ground level condo could have a great view, but think again! The living room looks out onto the inter coastal, so you can watch the boats go by. So picturesque and relaxing. The condo...
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Escape to your Siesta Key haven! This fully renovated 3-bedroom, 2-bath home, a mile from the world-famous beach, offers a perfect blend of comfort and convenience. Enjoy a modern open floor plan, a fully equipped kitchen, and a private pool in a fenced backyard. With comfortable sleeping arrangements...
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Escape to paradise at this beautifully remodeled 2-bedroom, 2-bath condo in a tranquil bayside complex on Siesta Key! This third-floor unit boasts a stylish open kitchen with granite countertops and stainless steel appliances, perfect for preparing meals. Enjoy comfortable living with tile flooring in...
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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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Welcome to our vacation oasis. We love the peaceful, friendly vibe of the Bay Oaks community and hope you do as well. Our two bedroom, two bathroom second floor condo unit has been recently upgraded with new living and dining room furniture and new bedding in relaxed but upscale style. The complex sits...
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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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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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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...
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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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...
Distance to beach: 0.1 miles to Siesta Key Beach
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Skip the parking hassle — you’re just steps from Siesta Key Beach, consistently ranked #1 in the U.S.This newly upgraded 2-bedroom, 2-bath condo is perfectly located directly across from the beach and minutes from Siesta Key Village. Walk, bike, or hop on the free trolley to reach top...
Featured review
Rented our condo from Christina it was everything she said it was. Condo very nice beds super comfy had a great time there would rent again.
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Discover your dream vacation in this beautiful 3rd floor walk-up Siesta Key condo! This 2-bedroom, 1.5-bath condo is located near the beach and offers a range of amenities, including pools, tennis courts, and a workout facility. Enjoy the convenience of a fully equipped kitchen and a comfortable living...
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Modern 1 bedroom, 2nd Floor unit in Siesta Key Village offers great location just two buildings from the beach and one block into the village with restaurants and shopping. The unit offers leather furniture, updated kitchen, 1 smart TV. Complex offers community pool and laundry facilities located just...
Featured review
Kitchen was well stocked, condo had everything we need. Would stay again. Bed was comfortable. Close to everything
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About this property
Updated 1 bedroom, 2nd Floor unit in Siesta Village offers great location just two buildings from the beach and 1 block into the village with restaurants and shopping. The unit offers tile floors, leather furniture, updated kitchen and TVs in living room and bedroom. Complex offers community pool and...
Featured review
We had a great vacation here! Condo was very nice, clean and well supplied. Close to Siesta Village, Beach and within walking distance of almost everything. A definite hidden treasure!
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2 queen size bedrooms, 2 bathroom , second floor end unit, adjacent from the pool, available for rent. Laundry availalbe on the first floor of the building. short walk to the ocean. Quiet and private space to relax and enjoy.
Distance to beach: 0.0 miles to Siesta Key Main Beach
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Water views everywhere from this Penthouse condo on Siesta Key! Taxes (13%) already included in my rates. Walk to beach. King bed in bedroom (and a Queen bed in living room if needed). Come and enjoy beautiful weather at the best beach in Florida! Heated Pools, Lighted Har-Tru Tennis Courts, Fitness...
Featured review
what a great find! A bright and lovely penthouse condo in a resort on Siesta Key. Easy walk to the beach, and the new Pickleball courts at the Main beach. Harbor Towers itself had a great pool, marina,...
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
3rd floor unit with no elevator. Clean but furniture not updated. Beach access but need to walk 3 blocks to an area to set up chairs and umbrella
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Experience the delightful simplicity of a tranquil beach getaway at Paisley's Casita. Nestled just a 7-property walk away from the serene vibes of Siesta Key Beach, this enchanting Studio Casita exudes similar charm to a hotel room whilst offering all the essential amenities for an undisturbed sojourn.Immerse...
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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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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
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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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Discover the perfect balance of comfort, charm, and Florida sunshine in this beautiful home, ideally located just a short stroll from the world-famous Siesta Key Beach and the lively Siesta Village, filled with restaurants, cafés, and boutique shops. Bedrooms & Comfort Left side of the home: • One...
Featured review
A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit...
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This tropical island get-away offers everything you desire for a magical, effortless vacation. Sunny, spacious second floor condo with easy indoor-outdoor living space including two queen bedrooms, each with an ensuite bathroom. Just steps to private, quiet powder-sand gulf beach and private fishing...
Featured review
This is a lovely immaculate condo in a lush green setting. From my window i watched birds, ducks, and turtles on the lake . On the sweet private beach i saw pelicans, dolphins and egrets. It's tempting...
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VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village...
Featured review
The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.
Distance to beach: 200 yards to Crescent Siesta Key Beach
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Welcome to Paradise at Midnight Cove I Siesta Key, FloridaLocated on consistently top-ranked Siesta Key Beach, our beautifully remodeled bayside condo at Midnight Cove I offers the perfect blend of luxury, comfort, and island charm for your next tropical getaway.Nestled within a lush, gated community...
Featured review
The condo had all the little things that we so appreciate , fabulous linens and the towels were top notch. Also the shower had fantastic pressure some times rare in a rental. The landscaping and canal views...
Distance to beach: 200 yards to Siesta Key Crescent Beach
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SIESTA SUMMER SAVINGS! UP TO 20% OFF YOUR SUMMER STAY BETWEEN 5/31/25 AND 9/1/25 WHEN BOOKING DIRECTLY ONLINE Online booking: Click link in Host information section of this listing and use promo code Anchor6415 at checkoutWe invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin',...
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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