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Siesta Key Family & Kid Friendly Rentals

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745 rentals in Siesta Key.
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Newly discounted rates! Maximum safety-smaller community, distancing compliant!
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Kid friendly
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1 other traveler has booked this property
Siesta Key Luxurious Beachfront Condo
2 bedrooms
2 bathrooms
Sleeps 6
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Peaceful Haven on Siesta Key with Beach Access
2 bedrooms
2 bathrooms
Sleeps 6
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GULF FRONT ON #1 Beach! Siesta Dunes (by owner)
2 bedrooms
2 bathrooms
Sleeps 6
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Cathy's Crescent Condos-Siesta Key, FL GULF FRONT
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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'Safe & Clean' Royal Palm Suite, Exceptional, Beach Views from all 3 balconies!!
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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4 other travelers have booked this property
Siesta Key - 2bdrm on the beach - amazing views!!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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28 other travelers have booked this property
BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key
3 bedrooms
2 bathrooms
Sleeps 8
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Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale
3 bedrooms
3 bathrooms
Sleeps 8
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Deluxe 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village
3 bedrooms
3 bathrooms
Sleeps 8
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1BR - Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta Key Village
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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1 other traveler has booked this property
Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Renovated!
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Beachfront Condo Siesta Key
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Enchanting Toes In The Sand Gulfront Condo
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Beachfront Dream Condo...You Deserve The Best!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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The Shells Villa - Next to Beach & Village
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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19 other travelers have booked this property
Cape Aqua
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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4 Bedroom with Gulf View Siesta Key FL Beach Fun
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Siesta Key-House of Sun, 2 bdrm/2 bath-Gulf View
2 bedrooms
2 bathrooms
Sleeps 6
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SAVE: Deep Discounts September 1 - November 21!!!!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
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33 other travelers have booked this property
Siesta Key private beach access
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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1 other traveler has booked this property
Crescent Arms 703S, Beachfront Penthouse, Gulf View from Every Room! 2BR-BA
2 bedrooms
2 bathrooms
Sleeps 5
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14 other travelers have booked this property
Best Deals on Siesta Key
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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2 other travelers have booked this property
A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, Kid friendly
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SEA SHELL - Siesta Key Beach View Vacation Condo - 2 BR - on Crescent Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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92 other travelers have booked this property
Siesta Key Villa B - Only 150 yds. to Crescent Beach and heated pool!
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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100 other travelers have booked this property
Sandy Toes Town Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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1 other traveler has booked this property
'Safe & Clean' -Honeymoon Suite - Gulf views - next to Siesta Key Beach
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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4 other travelers have booked this property
'Safe & Clean' Key West Suite next to Siesta Key Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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13 other travelers have booked this property
WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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42 other travelers have booked this property
Luxurious 2 BR Condo - Short Walk to Siesta Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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17 other travelers have booked this property
PALM'S HOUSE
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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3 other travelers have booked this property
Crescent Beach - 2 Bedroom - Beachfront Condo Complex - Heated Pool
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Jamaica Royale #92 on the #1 Beach in the USA!
2 bedrooms
2 bathrooms
Sleeps 6
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15 other travelers have booked this property
Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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1 other traveler has booked this property
Beachy Chic Condo in Siesta Key - Waterfront - Free wifi - Sleeps 4 !
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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68 other travelers have booked this property
2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
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66 other travelers have booked this property
WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY
2 bedrooms
2 bathrooms
Sleeps 4
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20 other travelers have booked this property
2BR2BA 800sqft 2nd Floor Siesta Key Crescent Beach Condo + WiFi No Road to Cross
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Kid friendly
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Reserve now! Beautiful Siesta key Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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27 other travelers have booked this property
Deluxe 4-BR Siesta Key Townhouse & Garden Apt - Heated Pool - Siesta Key Village
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Sunset Point Siesta Key FL AWESOME RENTAL !!
2 bedrooms
2 bathrooms
Sleeps 4
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16 other travelers have booked this property
Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Kid friendly
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37 other travelers have booked this property
Firethorn 232 at Midnight Cove Siesta Key
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Tropical Villa - Siesta Villa Palma
2 bedrooms
2 bathrooms
Sleeps 5
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15 other travelers have booked this property
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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.
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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.