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Distance to beach: 0.6 miles to Siesta Key Beach
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Welcome to your slice of paradise on Siesta Key—where coastal charm meets everyday convenience. This beautifully maintained single-family pool home offers the perfect blend of privacy, comfort, and proximity to the island’s natural beauty. Step outside and enjoy the lush, landscaped backyard,...
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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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Beautiful 4th floor condo with gulf views, a private beach, and a private fishing pier. This space was completely renovated in 2020 with all new features (including central AC) and furniture throughout. The fully-stocked kitchen is equipped with everything you need for a home-cooked meal. With a king...
Featured review
This modern beach condo is one of the best kept secrets of Siesta Key. While I had hoped to keep it that way, all I can offer is a ringing endorsement and review for the owners (who are incredibly kind...
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Minutes to Siesta Key, downtown Sarasota, hospital, restaurants, shopping, fitness and schools. Entertaining and seamless indoor/outdoor living from a large 17-by-37 resort-style pool with fountains, an alcove with a built-in table and seating is incredible, tranquil and relaxing. There is a hard-to-find...
Featured review
Owners Rachael & Sarab were wonderful during our stay and great to work with. The pool was as advertised, very large, great for a good sized family with kids. The home layout was great for our family as...
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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3 BR 2 Bath second story condo in the beautiful Heritage Oak Park. Completely furnished for seasonal use. Internet and all utilities paid. Development has beautiful pool, fitness room, library and clubhouse.
Featured review
This is a wonderful condo in a beautiful gated community. We had the pleasure of staying here in 2021 and were very pleased! ! The huge Heritage Oak trees throughout the community are stunning! The balcony...
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This beautiful home is brand new inside! It features 2 family rooms and a split floor plan that makes it perfect for families or 2 couples. Enjoy the morning breeze by the screened -in pool. The family room and Master Suite have French doors that open to the pool. 4 miles to siesta key, 3 miles...
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Featured review
We had a wonderful day at this house. It was lovely and exceeded our expectations. Nice quiet neighborhood and the pool is a great way to stay cool in the summer! We will definitely rent again from Chris...
Distance to beach: 3 miles to Famous Siesta Key Beach
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Whether you’re escaping winter or seeking a new sun‑filled home retreat, Granada Bungalow is waiting and is ideal for seasonal renters or families looking for a beautifully maintained home in a friendly, pet‑friendly neighborhood and highly rated Southside School District. It’s where timeless...
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...
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Come escape from ordinary in this stunning brand-new waterfront home located on Florida’s beautiful southwest coast. With sailboat access, a heated pool and spa, and an oversized U-shaped dock, this retreat offers endless opportunities for dockside sunsets, cool cocktails, and fishing adventures...
Distance to beach: 2 miles to Siesta Key beach
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OUR RATES:May -November $1999 December $3000 January $4200 February-March $4500 April $2500*Calendar months only. *Pet Friendly, Private Yard, First Floor Unit. *Community pool and gym in Complex. *Ask for our 6-month plus special rate *Boutique-style condominium community that offers:WELCOME...
Featured review
We stayed here for a clinical rotation from July - October at the Oasis on Osprey. It was truly a wonderful experience. Ana was always so helpful and attentive whenever we needed something. The area surrounding...
Distance to beach: 3 miles to Siesta Key
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My wife and I are recently retired educators. We ARE NOT multiple rental property owners. We own this one condo and are snowbirds from Pennsylvania. Our place is newly remodeled floor to ceiling! The Oasis complex is a prime location in close proximity to downtown Sarasota, Siesta Village, & nationally...
Featured review
This is the 2nd time we were renting this condo and couldn’t be more happier. We stayed this time for 3 months ( November through January 2026). We enjoyed the Christmas parade in December, downtown Sarasota...
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Contact: Erana Pulli or Joesgirl16@ Newly renovated condo. First-floor end unit with a beautiful, private courtyard. Large, light, bright, and airy best describes our home! Granite countertops and stainless steel appliances are found in our eat-in kitchen. Another large dining table off the living area....
Distance to beach: 1 miles to Siesta Key
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About this property
OUR RATES:April 2026 $3000 May-November 2026 2025 $2250 December 2026 $3000 January 2027 $4500 February 2027 $5000 March 2027 $5500*Calendar months only. *Ask for our 6-month plus special rate *Pet Friendly, Community pool and gym boutique-style condominium community that offers:WELCOME...
Featured review
It was a pleasure working with Ana (and her husband). The unit was clean, modernized, and comfortable. The area was very nice, quiet, friendly neighbors and kept clean. Location was good, plenty of restaurants...
Distance to beach: 1 miles to Siesta Keys
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Welcome to your stylish Sarasota retreat! This beautifully renovated 2-bedroom, 2-bathroom condo offers modern comfort and unbeatable convenience just minutes from the world-famous Siesta Key beaches. The primary bedroom has a king-size bed with an attached bath. The second bedroom has two queen-sized...
Featured review
We had a wonderful stay at this condo in Sarasota! It was exceptionally clean, comfortable, and perfectly located just across the north bridge to Siesta Key—making beach trips quick and easy. The condo...
Distance to beach: 12 miles to Boca Grande
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Immerse yourself in the soothing vibe of sunny Florida at this modern and bright 3-bed, 2-bath home. This Port Charlotte vacation rental is the perfect place for your next Gulf Coast getaway, featuring a heated outdoor pool for refreshing swims all year round, a screened lanai with a heater, and an open...
Featured review
We stayed the entire month of April. Beautiful home furnished with everything you need or want! The location is quiet and the pool is fantastic! We had family stay throughout the month and everyone was...
Distance to beach: 24 miles to Lido Key Beach
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A Horse‑Owner’s Dream Rental — Space, Privacy & Everything You Need for Happy, Healthy HorsesWelcome to 3717 Downer Ave, a rare Sarasota rental that truly caters to equestrians. Set on more than 5 peaceful acres in the Old Myakka area, this property offers the ideal environment for...
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Lido Key is the ultimate spot for your tropical vacation. This end unit condo has a two sided lanai. It is in a gated community at the Southern end of Lido Key. Wake up watching the sun rise and end the day watching the sunset all form the luxury of the condo with a cup of coffee or a relaxing cocktail....
Distance to beach: 50 yards to Lido Beach
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Welcome to our stunning ground floor condo, nestled directly on the pristine Gulf of America along a tranquil stretch of Lido Beach. Say goodbye to stairs and elevators – step right into your paradise!Completely renovated in 2025, this condo offers a fresh and modern retreat, designed with...
Featured review
We rented this gorgeous Condo for the month of March, 2024. First of all, the location is perfect, right on Lido Beach with a pool onsite and right down the street from St. Armand's Circle in Sarasota....
Distance to beach: 2 miles to Lido
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Relax at this lovely comfortable and spacious one bedroom or studio apartments with gorgeous new inground swimming pool at the Southside Village Resort. Check out our website for all the various options that are available. We are located in the wonderful Southside Village, also known as the Hillview...
Featured review
Fantastic. Like home away from home. great Hosts and beautifully located. Flat was sparkling clean and jason and Dee and their son Storm always on hand for any help required. We can only highly reccomend...
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Very pretty and updated 2 bedroom, 2 full bath home, with lovely outdoor living space. Master suite has it's own bathroom with new fixtures and vanity. King sized bed with brand new pillowtop mattress, double bedside tables, and large bureau as well as a walk in closet. Living room also has brand...
Featured review
I stayed for 2-months at Sandra's home and very much enjoyed my time there. The home is located in a modest, safe neighborhood and is only a few blocks away from Tamiami Trail and its many stores and restaurants....
Distance to beach: 100 yards to Lido Beach
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Quaint Studio on gorgeous Lido Key Beach in Sarasota.Heated pool right out the front door. Parking in front of the unit. Queen size bed with fully stocked kitchenette and open patio. Beach chairs, beach bag, cooler, and beach towels provided!
Featured review
Very accommodating,hostess could not have been more pleasant.Relaxing at its best.Excellent proximity to restaurants and shopping and entertainment.
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Family friendly, beautiful vacation home rental at the best RV resort in sunny Sarasota!1 bedroom plus extra queen bed with privacy screen on lanaiGuest accessGuests have full access to the outdoor heated pool, bar, grill and restaurant. If guests so choose, they may participate in any on...
Featured review
Sun Outdoors is such a fun place for any age. This home has been super cozy, has a washer/ dryer and golf cart. It is really adorable and has a large porch which increases the living space. The kitchen...
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Well kept 4 bed 2 bath pool home with easy access to 41, 776, Port Charlotte Beach Park and Punta Gorda. Our home is a perfect place to stay while on vacation or for the season. The house is in a quiet neighborhood on an oversized lot, almost an acre. Located close to 4 airports and short drive to some...
Featured review
A wonderful home that is clean and tastefully decorated. Great Location for ease of access to US 41 and Port Charlotte shops. Walking distance to Parks and a few restaurants and necessities. Owner was...
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