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Vacation Rentals in Siesta Key, FL

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$185
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1 / 7
1 Bedroom, 1 Bathroom, Sleeps 4
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$463
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1 Bedroom, 1 Bathroom, Sleeps 4
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$200
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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1 / 30
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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About this property
There's plenty of room for everyone here at Our House. We have a split-level living/dining area, with a large living room made for a crowd! The huge sectional sofa faces our new HDTV with DVD player, so anytime you need a little downtime from all the outdoor fun, settle in with your favorite movie,... View all property information
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$350
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1 / 18
3 Bedrooms, 2 Bathrooms, Sleeps 7
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  • Dishwasher
  • Grill
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  • Parking
  • Washer
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  • x
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  • x
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About this property
BEACH FRONT :Wander out 100 yards to the gorgeous white sand beaches of the Gulf of Mexico and only one block to SIESTA KEY VILLAGE! Our gorgeous three bedroom two bath beach-house is a one-of-a-kind private home with amazing water views from the private patio, (grilling on the patio: awesome!)... View all property information
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$166
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1 / 15
1 Bedroom, 1 Bathroom, Sleeps 4
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  • Satellite TV
  • Hot Tub
  • Terrace
  • Microwave
  • Stereo System
  • Stove
  • Deck
  • Air Conditioning
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Unique and rare large one-bedroom condo 4th floor penthouse with 200 sq. ft. open balcony featuring unobstructed and panoramic view of Siesta Key Public Beach and the Gulf of Mexico. This same view is also presented from the kitchen, dining room, living room and foyer. Balcony is a great location... View all property information
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$130
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1 / 16
1 Bedroom, 1 Bathroom, Sleeps 4
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  • Microwave
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  • Washer
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  • Ceiling Fans
  • Air Conditioning
  • Stove
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This one bedroom and one bathroom beach bungalow is located 150 yards away from the beach. You can walk to restaurants, shops and a great pool area. Queen bed and a sleeper sofa make it possible to sleep four. Enjoy your morning coffee on your private screened porch or while you walk on the beach.... View all property information
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$210
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1 / 21
9 Bedrooms, 9 Bathrooms, Sleeps 24
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  • Stove
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Siesta Key's newest beach house located across Beach Rd from access #7 to Siesta Key's Crescent Beach and one-block from the tropical Village of Siesta Key. Property has recently been completely remodeled and amenities include pool and spa, barbecue deck with lanai close to pool, free full property... View all property information
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1 / 22
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Internet Access
  • Shared Outdoor Pool...
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  • Single Beds:(2)
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
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About this property
Just steps from the bay, our newly remodeled condo in a gated Key West-style community is the perfect destination for your Siesta Key vacation. With resort amenities and the ideal location for beach and bay access, Gulf & Bay Bayside is irresistible! Relax in the large 11 x 16-foot lanai just off... View all property information
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1 / 20
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
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  • Elder access
  • ?
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About this property
With beautiful lagoon views from both the big lanai and the master bedroom, our condo at Castaway Cove is ideal for your Siesta Key vacation. Spacious and well equipped, the condo offers everything from bikes to a boat dock. Come play here very soon! Castaway Cove 3B sits right beside Blind Pass... View all property information
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1 / 22
1 Bedroom, 1 Bathroom, Sleeps 4
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  • Dishwasher
  • Stove
  • Patio
  • Ceiling Fans
  • Microwave
  • Dryer
  • Stereo System
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Village West # 101 is the perfect place for your Siesta Key Vacation. With rentals by the day, by the week, or longer this location is sure to please. Our newly Remodeled Siesta Key Ground Floor Apartment is in the heart of the Village of Siesta Key. This apartment is well appointed and... View all property information
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$90
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1 / 36
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Hot Tub
  • Internet Access
  • Number Of Bedrooms
  • Guest Count
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
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  • Smoking allowed
  • Elder access
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About this property
The accolades keep pouring in. Guests and media alike rate the Palm Bay Club as a perfect destination for romantic getaways and family vacations. Treat yourself to an idyllic holiday on Florida's Gulf Coast, at this luxury 4-person condo that is Gulf Side and next to the beach. Just a quick... View all property information
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1 / 52
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
  • Single Beds:(2)
  • Internet Access
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
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About this property
Roll into the lap of luxury and enjoy a unit that's still sparkling new. Siesta Key Gulf and Bay Club is known to be the finest long-stay resort in the area - and this newly renovated unit with a new air conditioning and heating system, Gulf and Bay Club 305C, trumps the competition. Sleeping 6,... View all property information
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1 / 18
5 Bedrooms, 1 Bathroom, Sleeps 20
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  • Microwave
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  • Patio
  • Dishwasher
  • Dryer
  • Parking
  • Grill
  • TV
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Tropical Garden beach cottages located at Siesta Key Beach. The Beach Place is Old Florida charm that's becoming hard to find. Private, quiet and relaxing. Tropical gardens surround our heated pool with tiki cabana bar for guests, poolside and beachfront BBQ. Five fully stocked one bedroom... View all property information
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1 / 13
1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Refrigerator
  • Patio
  • Dryer
  • Satellite TV
  • Ceiling Fans
  • Internet Access
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Please call David Butler before you send money to be sure you are not getting scammed, we do not accept wire transfers. This one bedroom is a large 700 sq. ft. condominium unit in a three unit building. There are two one bedroom units available and a two bedroom unit. You can add to your group... View all property information
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1 / 35
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Hot Tub
  • Number Of Bedrooms
  • # Of Bathrooms
  • Internet Access
  • Air Conditioning
  • Shared Outdoor Pool...
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
How long does it take you to walk 100 yards? Not very long at all. While on vacation at Crescent Beach, consider that your morning commute - from bed to pool. Enjoy the great convenience of a ground floor unit at Siesta Key's Jamaica Royale unit 91. Delight in the great value of this garden view... View all property information
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$113
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1 / 28
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Internet Access
  • # Of Bathrooms
  • Air Conditioning
  • Guest Count
  • Hot Tub
  • Shared Outdoor Pool...
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Siesta Key Florida House of Sun 307 rentals condos is very family-friendly, was recently renovated and has sensational sunset and Gulf views. Any questions? How about the added weight of the Travel Channel's endorsement, recently voting Siesta Beach as the 'Best Sand Beach' in the country? The... View all property information
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1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Number Of Bedrooms
  • Guest Count
  • Air Conditioning
  • Single Beds:(2)
  • # Of Bathrooms
  • Shared Outdoor Pool...
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Siesta Key's largest heated pool is begging for all the games and excitement you can give it. Ample pool beds and an adjacent covered area mean you can happily spend all day, every day, lazing around. From your 2 story split level condo, it's just steps to a perfect white sand beach. This is the... View all property information
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$100
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1 / 28
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Internet Access
  • Number Of Bedrooms
  • Guest Count
  • Shared Outdoor Pool...
  • # Of Bathrooms
  • Air Conditioning
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Take to the water or stick to the shore - the world is your proverbial oyster while staying at Siesta Key's Palm and Bay Club G88. Enjoy great comfort and value in this gulf-view suite, with all the resort amenities you can imagine. Two pools and a fantastic hot tub, a large fitness center and lit... View all property information
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$99
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1 / 18
2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Dryer
  • Air Conditioning
  • Refrigerator
  • Grill
  • Stove
  • Hot Tub
  • Microwave
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Island Reef is a magnificent condo facility located towards the southern end of Siesta Key. This top floor unit offers captivating views of the Gulf of Mexico, nearly 1450sqFt of living space, two bedrooms and two bathrooms. The master bedroom has a king size bed, access to the balcony, and great... View all property information
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$307
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1 / 16
3 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Parking
  • Washer
  • Garage
  • Grill
  • Microwave
  • Refrigerator
  • TV
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We have a beautiful two story beach house on the best beach in America! The sand is 99% quartz and white like powdered sugar, it's so perfect for sandcastles that every year The Crystal Classic is held with most beautiful sand sculptures. Our home is situated directly on the sand with 3... View all property information
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$1,995
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1 / 28
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Guest Count
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Every sunset is a memorable experience at our condo at Crystal Sands 406 in Siesta Key. Overlooking the placid Gulf of Mexico, our 4th-floor condo on the shores of Crescent Beach is a great venue for your next sun, sea, and sightseeing vacation! Rated one of the Top 10 Beaches of the World,... View all property information
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$100
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1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Internet Access
  • Shared Outdoor Pool...
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
  • Air Conditioning
  • Hot Tub
  • Single Beds:(2)
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Do you have children who'll delight in the geckos and insects they can discover in the garden? Or do you love nature and the sight and scents of tropical flowers? An idyllic ocean side condo perfect for energetic kids or families seeking added privacy, Siesta Dunes Beach 38A is your perfect... View all property information
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1 / 42
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
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About this property
Decked in pure tropical style, Siesta Dunes Beach 104 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it's easy on the wallet while its lovely atmosphere makes it a great home to... View all property information
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$3,500
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1 / 20
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Garage
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  • Parking
  • TV
  • Dishwasher
  • Hot Tub
  • Stove
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Tropical Retreat is a fabulous waterfront home in the middle of Siesta Key Village on “Boating Water.” You can walk to the beach, shops, boutiques, casual and 5 star dining. After a long day at the beach, enjoy the quiet confines of this beautifully updated home with HD TV's in all the bedrooms,... View all property information
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$561
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1 / 42
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Hot Tub
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  • Shared Outdoor Pool...
  • Number Of Bedrooms
  • Internet Access
  • Guest Count
  • Single Beds:(2)
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf & Bay Club 204C, you'll enjoy luxury and comfort in more than 1,500 sq ft of beachfront property, including a lovely lanai. And use of resort amenities is included! 28 day minimum stay. Gulf & Bay Club 204C is... View all property information
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$115
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1 / 6
2 Bedrooms, 1 Bathroom, Sleeps 4
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  • ?
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  • Elder access
  • x
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About this property
Enjoy the relaxed Siesta Key lifestyle at this comfortable 2 bedroom duplex on the beach side, just steps to award winning Siesta Key Beach. Experience swimming in the Gulf or at the beautiful community pool and then enjoy snorkeling at nearby Point of Rocks Enjoy a quieter area of Siesta Key,... View all property information
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$186
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1 / 8
1 Bedroom, 1 Bathroom, Sleeps 3
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  • Grill
  • Stereo System
  • Washer
  • Dryer
  • Stove
  • Garage
  • Dishwasher
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
THIS UNIT IS ALREADY BOOKED THROUGH April 20, 2015. Taking reservations for 2016 already. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. New Top of the Line King Size Bed will give you a great night sleep after a wonderful day at the beach and a great... View all property information
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$561
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1 / 47
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • # Of Bathrooms
  • Hot Tub
  • Internet Access
  • Single Beds:(2)
  • Shared Outdoor Pool...
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Gulf and Bay 502D will perfectly suit six nice people who deserve a month of total reward and relaxation on Crescent Beach. The resort club is unrivalled for repeat guest satisfaction and its location is smack in the middle of what the Travel Channel insists is the best sand beach in America. If... View all property information
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$129
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1 / 22
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Microwave
  • Stove
  • Refrigerator
  • Grill
  • Parking
  • Dryer
  • Ceiling Fans
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Welcome to Casita Salado of Villa Margarita! Enjoy an master bedroom featuring a colorful king size bed (sleeps 2) and en suite master bathroom, and a second bedroom with two twin beds (sleeps 2) and a separate living room with a very comfy, queen size sofa sleeper (sleeps 2) all of which... View all property information
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$329
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1 / 47
4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Patio
  • Garage
  • Linens Provided
  • Number Of Bedrooms
  • Private Outdoor...
  • Porch
  • Air Conditioning
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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 180ft. 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
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$129
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1 / 20
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Ceiling Fans
  • Microwave
  • Parking
  • Dishwasher
  • Stove
  • Washer
  • Satellite TV
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Sea Shell and Sea Wave Casitas are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. (Please note: These units can be rented separately. If one unit is not available, please inquire about the availability of... View all property information
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From
$295
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1 / 10
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Dryer
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  • Ceiling Fans
  • Deck
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  • Stove
  • Satellite TV
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This second floor unit is in a deluxe triplex building that was just fully remodeled to near new condition throughout. It will accommodate 6 people, but you can add one or two of the large one bedroom units in the building if you have additional guests or family coming, they sleep 4 each. The place... View all property information
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From
$229
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1 / 17
4 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Satellite TV
  • Microwave
  • Stove
  • Washer
  • Parking
  • Air Conditioning
  • Ceiling Fans
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Villa Brisa Marina or 'Sea Breeze' at 1119-1121 Crescent Street is an exciting new 4BR/4BA/2Kit home just added to our boutique collection of fine vacation homes and it's sure to be a standout. This home features a brand new heated pool and a three minute walk to the Nation’s finest beach [no major... View all property information
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From
$450
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1 / 24
4 Bedrooms, 3 Bathrooms, Sleeps 12
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  • Stove
  • Refrigerator
  • Parking
  • DVD Player
  • Air Conditioning
  • Dishwasher
  • Microwave
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Quality rental, tastefully furnished and nice open entertaining plan. New swimming pool to be installed April 17th to May 22nd, 2015. 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 is only a half of a... View all property information
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4 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Washer
  • Ceiling Fans
  • Microwave
  • Grill
  • Dryer
  • Dishwasher
  • Satellite TV
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Villa Fiesta at 1115 Crescent Street is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to The Cottages collection of fine vacation homes. Villa Fiesta and its sister home, Villa Margarita are two beautiful 4-BR pool homes offering unique sleeping combinations to larger... View all property information
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$229
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4 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Grill
  • Dryer
  • Refrigerator
  • Air Conditioning
  • Stove
  • Washer
  • Ceiling Fans
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Villa Margarita located at 1109-1111 Crescent Street is a vibrant, festive newly decorated four bedroom/four bathroom/two kitchen home now available for vacation rentals with The Cottages. It’s the latest standout in our boutique collection of fine vacation homes now available for larger groups or... View all property information
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • VCR
  • Stereo System
  • Dryer
  • Satellite TV
  • Dishwasher
  • Air Conditioning
  • Refrigerator
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beautiful villa and gaze across the expansive living area, then further out across the... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Hot Tub
  • Internet Access
  • Air Conditioning
  • Shared Outdoor Pool...
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
  • Single Beds:(2)
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it's easy on the wallet while its lovely atmosphere makes it a great home to... View all property information
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$257
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Microwave
  • DVD Player
  • Washer
  • Parking
  • Grill
  • Dishwasher
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Welcome to “Casa De Suenos”, one of the most fabulous vacation homes in Siesta Key. Newly constructed in 2013! The magic begins as you enter the foyer of this beautiful casa and gaze across the expansive living area, and deck area. You know already you made the right choice for your family and... View all property information
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$414
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4 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • Patio
  • Stove
  • Grill
  • Hot Tub
  • Refrigerator
  • Washer
  • Garage
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
THE GRAND CANAL COTTAGE: (Two Week Minimum Rental) The Grand Canal Cottage, perhaps one of Siesta Key’s favorite luxury vacation homes, is a highly landscaped canal-front private luxury home featuring a heated pool with sun shelf and a separate 8-person spa. It is situated on Siesta Key within... View all property information
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3 Bedrooms, 3 Bathrooms, Sleeps 7
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  • Dishwasher
  • Dryer
  • Parking
  • Patio
  • Stove
  • Refrigerator
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Caution: I do not ask for wire money transfers so if someone asks you to wire money, then it is fraudulent. It is best to contact me directly at some point to get to know me so that you can ask questions and feel comfortable that you are renting from a reputable individual and not being scammed.... View all property information
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$229
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4 Bedrooms, 1 Bathroom, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Refrigerator
  • Ceiling Fans
  • Parking
  • Dishwasher
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Villa Dom Brisa or 'Sun Breeze' at 1123-1125 Crescent Street is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to our boutique collection of fine vacation homes at The Cottages. This home is part of the Las Brisa complex of two beautiful 4-BR homes offering unique... View all property information
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$138
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Dishwasher
  • DVD Player
  • Stove
  • Refrigerator
  • Microwave
  • Patio
  • Parking
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Our vacation home is just steps away from the #1 rated beach in the USA - Siesta Key beach. It is in a complex located on the GULFSIDE (or Beach side) of the island. It is a comfortable villa with a master bedroom, guest bedroom, living room, kitchen with dining area, and a bath and a half.... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Washer
  • Refrigerator
  • Microwave
  • Stove
  • Dishwasher
  • Patio
  • Dryer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Location, Location, Location! Siesta Key #1 Beach in USA Our condo is only a 3 minute walk to Crescent Beach on beautiful Siesta Key FL. Siesta Key Beach rated #1 beach in the USA. We rent by the month or for the season. Our two bedroom, two bath has a screened in lanai, large great room with all... View all property information
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$395
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4 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Parking
  • Washer
  • DVD Player
  • Garage
  • Grill
  • Dryer
  • Refrigerator
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This is one of the nicest rental properties that you will find on Siesta Key! It has views that are to die for of the bay looking east, south and north to Downtown skyline plus it has some Gulf of Mexico views looking west. All rooms in the house have something special to admire and enjoy. There... View all property information
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$250
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Stove
  • Garage
  • TV
  • Grill
  • Refrigerator
  • Dishwasher
  • Patio
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Island Bliss is one of the most elegant and comfortable houses that Siesta Key has to offer. This is one of the rare houses that is conveniently located behind The Village of Siesta Key and still has its own private dock on a canal. Ride your bike or walk to the beach and all the great shops and... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Shared Outdoor Pool...
  • Number Of Bedrooms
  • Air Conditioning
  • Hot Tub
  • Guest Count
  • Internet Access
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Love sunsets? How about white sand, plush beds, a choice of three pools, swans ... and a little shuffleboard? If this sounds like a month or more of paradise, you'll immediately love life at Siesta Key Gulf and Bay Club #102B. Book now for a stay of 28 or more days. This ground floor condo is... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Single Beds:(2)
  • Shared Outdoor Pool...
  • Air Conditioning
  • Guest Count
  • Hot Tub
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf & Bay Club #409 is guaranteed bliss. Confirmed to be the 'Best Sand Beach in America' by the Travel Channel, Siesta Key's residents and renters alike know they've got a very good thing. On Florida's... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Number Of Bedrooms
  • Air Conditioning
  • Single Beds:(2)
  • Internet Access
  • # Of Bathrooms
  • Guest Count
  • Shared Outdoor Pool...
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Nestled on the southern tip of Siesta Key is our ground-floor condo, Bay Tree Club 106. Located in an oceanfront complex, it will pamper you with brand-new HDTVs, spacious and well-appointed rooms, and a sunny lanai overlooking grassy grounds. The Gulf of Mexico is just steps away from Bay Tree... View all property information
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Suitability

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Siesta Key Vacation Rentals

Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key vacation rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theater, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.

Lions, Tigers & Circuses

When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.

Gardens & Aquariums

Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.

Locomotives & Science

Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theater, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.

History & Baseball

From your money-saving Siesta Bay vacation rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.