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Siesta Key Luxury Rentals

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    Travelers to Siesta Key are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    8 Bedrooms, 6 Bathrooms, Sleeps 22 | Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Beachfront Townhome in Siesta Key Village Area. Located on Sunset Point, directly on the beach, this Vacation Home has it all. Walk out of your front door or single car garage, and directly on to the pearly white sands of Siesta Key. This 5 bedroom 4 bath completely remodeled home has one of a... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    5 of 5 bubbles (7) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    4,000 SQ FT BEACHFRONT HOME 1/2 mile from Village! 4 Bedroom + Media Room - 5 Bathroom - Sleeps up to 14 and is ON THE BEACH!!! NOTE: Our home is NOT listed on Craig's List. If it is represented there it is fraudulent. Located directly on the beautiful white sands of Siesta Beach! 636... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Perfectly located, New, 6 bedrooms 4 1/2 bathrooms private home,in a gated community, combines luxury with convenience of location. We offer you a large 6000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed April 9, 2017
    View from master bedroom was fantastic. Plenty of room for the 14 of us. Will defiantly book again. Kitchen had all appliances needed. Grill was old and had to light with a...
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    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    What a House. Sleeps 10+ people in Beds. Almost Beachfront, less than 100 yards to the beach and Siesta Key Village. This home is a 4 bedroom, 4 bathroom home located on Sunset Pointe. Immediately upon entering the home you'll notice the raised celing and spacious feel of the home. The spacious... View all property information
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    Siesta Key, Florida 34228
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    NEWLY LISTED SIESTA KEY WATERFRONT ESCAPE!!!! Brand New , Gated Residence steps from Siesta Key Beach . Perfect location between the village and crystal sands of Siesta Beach!! Bar's, Restaurants, Shopping, Sport Rentals……..EVERYTHING is within walking distance…..NO CAR NEEDED!!! This brand new... View all property information
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    Siesta Key, Florida 34242
    1 / 24
    8 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    This is a wonderful Siesta Key Waterfront Home just steps to the main Siesta Key beach!!!! ( only 1 BLOCK away) An expansive 2700 sq ft residence, this home contains 8 bedrooms, 3 baths and situated directly on the water. This perfect location is right in the middle of siesta key; between the... View all property information
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    Siesta Key, Florida 34242
    1 / 13
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Escape to your own secluded tropical oasis. Lush island landscaping surrounding the property makes this home a unique and private setting. Private dock on protected cove 2 minutes from Sarasota Bay/ICW. Rent a boat at neighboring marina if you choose. Breathtaking large private pool, with numerous... View all property information
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    Siesta Key, Florida 34242
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    1 / 4
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Hyatt siesta key is a residence club with hotel amenities. Perfect location on crescent beach. Many bars and restaurants close by. The facility offers valet parking,unground pool and spa,private beach,gym,grill,fire pit,bar,complimentary breakfast,housekeeping,chefs kitchen and many other... View all property information
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    Siesta Key, Florida 34242
    1 / 25
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    Bayfront Contemporary Home on Sarasota Bay! This Contemporary Home on Sarasota Bay has Spectacular Views from all 3 stories. Enjoy bayfront living at it's finest with a 2-story great room, bayfront lanai, pool, boat dock and lift. Perfect for Family Gatherings, Wedding Parties, Birthdays and... View all property information
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    Siesta Key, Florida 34231
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Beachfront Townhome in Siesta Key Village Area. Located on Sunset Point, directly on the beach, this Vacation Home has it all. Walk out of your front door or single car garage, and directly on to the pearly white sands of Siesta Key. This 3 bedroom 3 bath home has one of a kind views from... View all property information
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    Siesta Key, Florida 34242
    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beachfront Townhome in Siesta Key Village Area. Located on Sunset Point, directly on the beach, this Vacation Home has it all. Walk out of your front door or single car garage, and directly on to the pearly white sands of Siesta Key. This 3 bedroom 3 bath home has one of a kind views from... View all property information
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    Siesta Key, Florida 34242
    1 / 36
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    308-2 Calle Miramar is just across the street from the beach and less than a block to Siesta Key Village. Located in a gated community with its' own private heated pool and hot tub, park your vehicle(s) inside the large 2 car garage, use the elevator to travel to the 3rd and 4th floor condo plus a... View all property information
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    Siesta Key, Florida 34242
    1 / 32
    4.5 of 5 bubbles (6) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    NOTE** If you see my property on Craigslist it will be a scam because I do not use Craigslist. Weekly Rental on Siesta Key, 700 Feet from the #1 rated Beach in the USA and the Village shops and Restaurants. Just park your car because everything is an easy walk from this property. Live... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed July 8, 2016
    my family had a wonderful week at Siesta Sandcastle (May 28-June 4). The accommodations were great, and the location was perfect. Our group included my husband and me and our five...
    3 of 5 bubbles Reviewed April 25, 2016
    The condo itself was pretty good - three bedrooms and clean living area. Living room and kitchen not big enough to handle 6 adults. Many amenities missing or lacking i.e...
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    1 / 24
    5 of 5 bubbles (11) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Quality rental, tastefully furnished and nice open entertaining plan. New private swimming pool. This home is located in a excellent location, very near Siesta Key Public Beach. It is convenient to Siesta Key Village, about 4 blocks and it is only a half of a block to the white quartz sands of... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed March 21, 2016
    We had a wonderful week in Siesta Key in this beautiful home. With four bedrooms, we had plenty of space, the kitchen is well stocked, the two balconies provide outdoor places to...
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    1 / 7
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Newly remodeled with a tiled Kitchen & Bath and new furnishings. -Two King Beds -Two Full Baths -CATV in All Bedrooms -Granite Countertops -Fully Equipped Kitchen -Stainless Appliances -Two Twin Beds -Private Patio -Pullout Sleeper -Laundry in Unit -VCR/DVD -Gas Grill NOTE: PLEASE... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed June 30, 2015
    Very nice property and you would be hard pressed to find a better location. Peace and quiet of the beach and only 1 block away from fun and nightlife of the Village. Loved it !
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    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    View of Roberts Bay / Near Beaches / Great Shopping & Dining Get lost in the intoxicating relaxation of Siesta Key, in this luxurious private home. This tropical retreat is a single-family residence located at the end of a secluded dead end street in the opulent neighborhoods of northern Siesta... View all property information
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    Siesta Key, Florida 34242
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Get used to shaking the sand out of your shoes because this Beach House is basically on the beach. If you love looking at the beach, the gulf, and having Siesta Key Beach in your back yard, this is the rental home for you. Oh ya, and it also has Daily Housekeeping service so this unit will stay... View all property information
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    Siesta Key, Florida 34242
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    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    3 Bedroom, 2.5 Bath Pool House on beautiful Siesta Key. This great beach bungalow home will sleep 8 people in beds. The third bedroom offers a great value as it is set up as a studio with it's own bathroom and kitchenette. This works out great for extended families, group trips, or for those... View all property information
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    Siesta Key, Florida 34242
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    Wow! What a view! Gulf/Beach views from the living area and the master bedroom! Oh ya, and don't forget about the roof top deck that provides stunning views of Siesta Key Beach and our gorgeous coastline and Gulf. The home itself is conveniently located directly across from Siesta Key Beach... View all property information
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    Siesta Key, Florida 34242
    1 / 25
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Beach and water front on Gulf Of Mexico. A block from Siesta Key Village for lite and fine dinning, fun, shopping and nightlife. Two Master Suite King Bedrooms with Master Bath for each. Sauna, four Mexican tiled decks with panoramic views of the Gulf and beaches. Fishing Pier. Leather, stone... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed March 27, 2017
    The location is fabulous! A wonderful view with so much privacy as well as close to great shopping in the village shops. We should also complement the great food served at the...
    5 of 5 bubbles Reviewed January 6, 2016
    THE best spot in the US to see the sunset over the Gulf of Mexico! A starting point for a long beach walk on Siesta Key's white sands as it is just steps to the beach. A short...
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    1 / 34
    4.5 of 5 bubbles (13) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Prominently featured in the 2013 and 2014 in NYJL House Tour Magazine and winner Spring of 2014 Top Auction Item. Brought to you by Gertrude Rentals! This Spanish revival home is located on Palm Island, the heart shaped island within the island of Siesta Key, just steps from the beach and one... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed December 4, 2015
    We loved this home! We had a large group and it never felt crowded. The house is lovely and very convenient to everything! Highly recommend this rental!
    5 of 5 bubbles Reviewed December 3, 2015
    Just want to say thank you for creating the perfect venue to celebrate my Mom's 90th Birthday! Seven siblings convened from across the globe to share a very special time together...
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Siesta Sun Villa Our home is one large house that has a 3 bed 2 bath unit. A 2 bed 1 bath unit and a 1 bed 1 bath unit. All with connecting doors so you can rent the whole house to sleep 12 guests all in beds. It is perfect for large familys, Weddings and reunions. Private back yard, Overlooking a... View all property information
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    Siesta Key, Florida 34242
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Siesta Key Townhouse on Gulf side with a 300yd walk to the #1 beach in the U.S. Spacious 3 bedroom 3 bath Townhouse with one car garage and guest parking. Beautifully decorated beach type atmosphere, shared heated pool within the Midnight sea complex (12 units).. Located within walking... View all property information
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    Siesta Key, Florida 34242
    1 / 37
    5 of 5 bubbles (5) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Oh what a great feeling you get when you are looking out over the pool to the relaxing waters of the Grand Canal. This home is special with 188 ft. of canal wrapping the back of the home so you get to enjoy the views from three bedrooms, the kitchen, living and two dinning areas. Open all the... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed August 12, 2015
    Stayed at this house for two weeks in July. Pictures do not do this house justice. House was much more beautiful. Views of the canal, that can be seen from all along back of home...
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    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Location, Location!!! Come relax, our beautiful home is only 2.5 miles from the #1 beach in the US, Siesta Key!! It has northern charm with wood burning fireplace, wood floors and a florida cottage feel! Beautifully landscaped backyard, fenced in and private. Brand new kitchen, with overized eat... View all property information
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    Siesta Key, Florida 34231
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the beach. The entire back of this house opens with... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    This property is walking distance to the village, less than 100 yards, and just 2-3 short blocks to the beach depending on which beach access you choose. This home is a spacious 2 bedroom 2 bathroom home, with a shared pool. What an amazing property. Siesta Key Village is literally in your front... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    This property is walking distance to the village, less than 100 yards, and just 2-3 short blocks to the beach depending on which beach access you choose. This home is a spacious 2 bedroom 2 bathroom home, with a shared pool. What an amazing property. Siesta Key Village is literally in your front... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Enjoy your vacation in this beautifully decorated beachfront 3 story 4 bed/3.5 bath townhouse! The sparkling blue water and white sand of Crescent Beach is just steps away. The first floor has a full size living room with a TV,DVD,VCR; two bedrooms...one with a queen bed and one with 2 twin beds... View all property information
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    Siesta Key, Florida 34242
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    REMODELED - PRIVATE POOL - Forget your busy life and come and drift away at your own private pool house paradise. This 2 Bedroom and 1 Bathroom Suite is a unique property and a new type of rental here at Tropical Breeze. It offers such an awesome opportunity for our guests to experience the more... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    5 of 5 bubbles (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed January 20, 2017
    This was our 6th year staying at Fishermans Cove in Siesta Key, Unit 208, 8900 Blindmans Pass. We become very comfortable during our three weeks in this waterfront condo. The...
    5 of 5 bubbles Reviewed June 26, 2016
    This condo was perfect for relaxing beachfront in a beautiful, secluded location. The view was amazing, with the gorgeous gulf beach out back and the bay out front! And the...
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Quiet and serene, but close to local attractions, you will love this large 4 bedroom, family friendly home with 2 kitchens, new appliances, modern furnishings, and beach buggy with all the gear! Separate living areas can accommodate one large family or two smaller ones. Each living area has its... View all property information
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    Siesta Key, Florida 34242
    1 / 6
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    2+ Bedroom Near Beach Suite The Master bedroom has a King Bed and Glamorous Bath. Second Bedroom has a Queen Bed and a private bath. The Den has a pullout Queen sofa sleeper. Fully equipped Cottage style kitchen with corian countertops. Washer dryer WIFI.Private tropical back patio/pool has... View all property information
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    Siesta Key, Florida 34242
    1 / 7
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Privacy, Luxury, 99 steps to the beach. The Master bedroom has a KIng Bed and Glamorous Bath. Second Bedroom has a queen bed and a private bath. The Den has a pullout queen sofa sleeper. Fully equipped Gourmet style kitchen with granite countertops and stainless steel appliances. Washer Dryer,... View all property information
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    Siesta Key, Florida 34242
    1 / 5
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Newly remodeled with a tiled Kitchen & Bath and new furnishings. -TWO Full Baths -King Bed -Queen Bed -Pullout Queen Sleeper -Fully Equipped Kitchen -VCR/DVD -CATV -WiFi -Dishwasher/Micro -Patio/Gas Grills- -Laundry Facilities on site NOTE: PLEASE CONTACT US FOR AVAILABILITY. We do... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed March 14, 2016
    My husband and I along with couple of our closest friends stayed here for the week. Everything was wonderful! Views are amazing and house was very pretty and had everything we...
    5 of 5 bubbles Reviewed January 13, 2016
    I was looking for a place on or near the beach for a little get away with my daughter while she was home on break. Came across the Sandbox and decided to give it a try. It was a...
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    1 / 27
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Forget your busy life and come and drift away on our beautiful resort. This Deluxe 2 Bedroom and 1 Bathroom unit is rented as it's own is truly a home away from home, and it features everything you'll need during your vacation, including a full kitchen, pots and pans, dishes, cups, utensils,... View all property information
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    Siesta Key, Florida 34242
    1 / 35
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    REMODELED 2 Bedroom Suite - Forget your busy life and come and drift away at your own private paradise. This Deluxe 2 Bedroom and 1 Bathroom resort room is a unique property, and a new type of rental here at Tropical Breeze and it offers such an awesome opportunity for our guests to experience a... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Luxury hi-rise condo right on the beach. Enjoy amazing sunsets on the full lanai, with access from each bedroom. Take long walks on the beach. Location is close to shops and restaurants. Crystal Sands on Midnight Pass Rd is one of the most popular condos in Siesta Key. And our Crescent Beach is... View all property information
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    Siesta Key, Florida 34242
    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Description Details Features Inquires Similar Listings google-map-thumb Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front USD 160 Per day 6312 Midnight Pass Rd., Siesta Key slider PreviousNext Property Description Relax in this beautiful fifth floor beach front Condo... View all property information
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    Siesta Key, Florida 34242
    1 / 25
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Welcome to Villa Vista Mare! This beautiful and luxurious 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed April 14, 2017
    Great spot right across from the beach - which is about the best beach you'll ever see. Pool offers a nice change of pace. Panaramic view from the entire living area and the...
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    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This gorgeous townhouse is located 2 short blocks from Siesta Key Village and a block from the white sands of Siesta Key Beach. VIew the gorgeous sunset and Gulf and beach views from the Master Bedroom on the top level. This unit is immaculately appointed and will make your Siesta Key Vacation... View all property information
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    Siesta Key, Florida 34242
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Spacious 3 bedroom 2 bathroom, 1/2 duplex, that sleeps 10 people in beds! This property is located directly across from Siesta Key Beach Access 10, and it is 2 blocks to Siesta Key Public Beach and 4 blocks to Siesta Key Village. You can walk or bike to everything! The home itself has been... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    *** Great Condo for a Family Vacation *** Unit #107 completed a MAJOR renovation on Oct 1st, 2013. Updates include Professional decorating, new tile floors throughout, new tile & Granite in all 3 Bathrooms (2 with walk-in Showers and 1 with Bathtub), Granite in Kitchen and Baths, All new doors,... View all property information
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    Siesta Key, Florida 34242
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Our high-rise Condo located in Crystal Sands Resort unit #1102, 11th floor, gives our guests a panoramic view of the beautiful Crescent Beach on Siesta Key. Watch the Sun rise in the morning and set in the evening from our unique Southwest balcony view. Our thirty-five foot balcony is accessed from... View all property information
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    Siesta Key, Florida 34242
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    A total renovation of Siesta Dunes #4-6216A completed December 2014. Everything is new inside and out, new furnishings throughout this 2 bedrooms, 2 baths plus a 3rd bedroom private efficiency suite on the lower level with full bathroom and a private 1 car garage. Reserve the whole building #6216B... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 2 days ago
    Morgan properties knows how to make you feel special with his luxury beachfront condo. This Siesta Dunes condo was beyond perfect! Extremely clean, great location, updated...
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    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    You will have a visit to remember in this elegant three bedroom, two and one half bath vacation condo with a path to the famous Siesta Key white sand beaches just out your door! Two levels with tiles lanais and Gulf views from each level. Enjoy the amazing Gulf Coast sunsets right from your own... View all property information
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    Siesta Key, Florida 34242
    1 / 29
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Welcome to Casa La Joya! This gorgeous freshly remodeled beach cottage is the perfect getaway for you and your closest friends and family! The décor is beautifully done and so reminiscent of the seashore and beach [found only in the Point of Rocks area]. It’s clearly luxurious here. Enjoy a... View all property information
    Location Information
    Siesta Key, Florida 34242
    Siesta Key Flight and Weather Info
    Airports nearby (1)
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    SRQ
    Bradenton Airport
    8.7 miles from Siesta Key
    Low airfares recently found by TripAdvisor travelers
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    Additional Siesta Key Info

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    • Local time: 02:23 PM (EDT)
    • Peak travel: February - April