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Siesta Key Beach Rentals

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939 rentals in Siesta Key.
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Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!, vacation rental in Siesta Key

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key-#1 Beach,  2017 Renovation w/ private entrance,  Intracoastal/Marina, vacation rental in Siesta Key

Siesta Key-#1 Beach, 2017 Renovation w/ private entrance, Intracoastal/Marina

2 bedrooms
2 bathrooms
Sleeps 4
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CHATEAU du SOLEIL         10% DISCOUNT Dec 5-19, vacation rental in Siesta Key

CHATEAU du SOLEIL 10% DISCOUNT Dec 5-19

4 bedrooms
3 bathrooms
Sleeps 11
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Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale, vacation rental in Siesta Key

Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale

3 bedrooms
3 bathrooms
Sleeps 8
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WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY, vacation rental in Siesta Key

WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY

2 bedrooms
2 bathrooms
Sleeps 4
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Beachfront Getaway in Siesta Key, vacation rental in Siesta Key

Beachfront Getaway in Siesta Key

1 bedroom
1 bathroom
Sleeps 4
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Cathy's Crescent Condos-Siesta Key,  FL GULF FRONT, vacation rental in Siesta Key

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*, vacation rental in Siesta Key

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*

2 bedrooms
2 bathrooms
Sleeps 6
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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key, vacation rental in Siesta Key

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

3 bedrooms
2 bathrooms
Sleeps 8
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Siesta Key Inn - 1Br/1B Sabal Palm #2A, vacation rental in Siesta Key

Siesta Key Inn - 1Br/1B Sabal Palm #2A

1 bedroom
1 bathroom
Sleeps 4
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Siesta Key Beach Cottages on Crescent, vacation rental in Siesta Key

Siesta Key Beach Cottages on Crescent

2 bedrooms
2 bathrooms
Sleeps 6
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WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY, vacation rental in Siesta Key

WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY

2 bedrooms
1 bathroom
Sleeps 4
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Siesta Villa Coralline, vacation rental in Siesta Key

Siesta Villa Coralline

2 bedrooms
1 bathroom
Sleeps 5
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Siesta Key Beachfront Condo with Gulf View!, vacation rental in Siesta Key

Siesta Key Beachfront Condo with Gulf View!

1 bedroom
1 bathroom
Sleeps 4
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New Listing! Charming Island Getaway - Steps to Sand, Walk to Dining & Shops, vacation rental in Siesta Key

New Listing! Charming Island Getaway - Steps to Sand, Walk to Dining & Shops

1 bedroom
1 bathroom
Sleeps 4
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Luxury Romantic Oceanfront Siesta Beach Condo #304, vacation rental in Siesta Key

Luxury Romantic Oceanfront Siesta Beach Condo #304

1 bedroom
1 bathroom
Sleeps 4
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Newly discounted rates! Gorgeous one bedroom across from beach, near village!, vacation rental in Siesta Key

Newly discounted rates! Gorgeous one bedroom across from beach, near village!

1 bedroom
1 bathroom
Sleeps 3
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Siesta Key Inn 1Br/1B Pineapple Palm #2D, vacation rental in Siesta Key

Siesta Key Inn 1Br/1B Pineapple Palm #2D

1 bedroom
1 bathroom
Sleeps 4
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Island House Beach Resort 15N, vacation rental in Siesta Key

Island House Beach Resort 15N

2 bedrooms
2 bathrooms
Sleeps 4
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Island House Beach Resort V27, vacation rental in Siesta Key

Island House Beach Resort V27

2 bedrooms
2 bathrooms
Sleeps 6
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Stunning 2 Bedroom/ 2 Bath by Siesta Key Beach, Sunlight Sensation!!, vacation rental in Siesta Key

Stunning 2 Bedroom/ 2 Bath by Siesta Key Beach, Sunlight Sensation!!

2 bedrooms
2 bathrooms
Sleeps 6
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Newly Listed... NEW Decor by Jan 10th 2021!  Walk to SK Beach, 2 Heated Pools, W, vacation rental in Siesta Key

Newly Listed... NEW Decor by Jan 10th 2021! Walk to SK Beach, 2 Heated Pools, W

3 bedrooms
2 bathrooms
Sleeps 8
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Location. 3 bedroom cottage block from beach and two blocks from Siesta Village, vacation rental in Siesta Key

Location. 3 bedroom cottage block from beach and two blocks from Siesta Village

3 bedrooms
3 bathrooms
Sleeps 8
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Charming Siesta Key Village  Unbeatable Location, vacation rental in Siesta Key

Charming Siesta Key Village Unbeatable Location

1 bedroom
1 bathroom
Sleeps 4
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Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach, vacation rental in Siesta Key

Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach

2 bedrooms
2 bathrooms
Sleeps 4
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Very Clean! 2 min. drive to Siesta Key! Stay a few nights or a month!, vacation rental in Siesta Key

Very Clean! 2 min. drive to Siesta Key! Stay a few nights or a month!

2 bedrooms
2 bathrooms
Sleeps 4
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Island House Beach Resort 8N, vacation rental in Siesta Key

Island House Beach Resort 8N

2 bedrooms
2 bathrooms
Sleeps 4
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Bright & Beachy - Steps to the Water!, vacation rental in Siesta Key

Bright & Beachy - Steps to the Water!

2 bedrooms
1 bathroom
Sleeps 7
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Peaceful Haven on Siesta Key with Beach Access, vacation rental in Siesta Key

Peaceful Haven on Siesta Key with Beach Access

2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Beach Zen Den, vacation rental in Siesta Key

Siesta Beach Zen Den

1 bedroom
1 bathroom
Sleeps 4
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Siesta Beach House #211 Beautiful Updated Unit, vacation rental in Siesta Key

Siesta Beach House #211 Beautiful Updated Unit

2 bedrooms
2 bathrooms
Sleeps 7
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2 BR, 2 Bath, Siesta Key Village Condo with Pool, vacation rental in Siesta Key

2 BR, 2 Bath, Siesta Key Village Condo with Pool

2 bedrooms
2 bathrooms
Sleeps 4
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GULF FRONT ON #1 Beach! Siesta Dunes (by owner), vacation rental in Siesta Key

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach, vacation rental in Siesta Key

A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach

3 bedrooms
2 bathrooms
Sleeps 9
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Quiet and Comfortable Condo Near Turtle Beach, vacation rental in Siesta Key

Quiet and Comfortable Condo Near Turtle Beach

2 bedrooms
2 bathrooms
Sleeps 5
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Siesta Key Old Florida Cottage, Great Location at a Great Price, vacation rental in Siesta Key

Siesta Key Old Florida Cottage, Great Location at a Great Price

1 bedroom
1 bathroom
Sleeps 2
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Excelsior- 102 G-great Gulf side location!- 1 WEEK MIN RENTAL, vacation rental in Siesta Key

Excelsior- 102 G-great Gulf side location!- 1 WEEK MIN RENTAL

2 bedrooms
2 bathrooms
Sleeps 4
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4 Bedroom with Gulf View Siesta Key FL Beach Fun, vacation rental in Siesta Key

4 Bedroom with Gulf View Siesta Key FL Beach Fun

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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SHARK UNIT-THE BEST SPOT ON SIESTA KEY BEACH & VILLAGE! !, vacation rental in Siesta Key

SHARK UNIT-THE BEST SPOT ON SIESTA KEY BEACH & VILLAGE! !

3 bedrooms
3 bathrooms
Sleeps 12
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Ground floor unit with quick access to Siesta Beach Amenities, vacation rental in Siesta Key

Ground floor unit with quick access to Siesta Beach Amenities

2 bedrooms
1 bathroom
Sleeps 6
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FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!, vacation rental in Siesta Key

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!

2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Crescent Beach on Siesta Key One of the, vacation rental in Siesta Key

Beautiful Crescent Beach on Siesta Key One of the

2 bedrooms
2 bathrooms
Sleeps 4
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Direct Gulf-Front / End Unit Fisherman's Cove A201, vacation rental in Siesta Key

Direct Gulf-Front / End Unit Fisherman's Cove A201

2 bedrooms
2 bathrooms
Sleeps 4
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Sandy Toes Town Home, vacation rental in Siesta Key

Sandy Toes Town Home

3 bedrooms
3 bathrooms
Sleeps 6
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Chinaberry 911 at Midnight Cove Siesta Key, FL., vacation rental in Siesta Key

Chinaberry 911 at Midnight Cove Siesta Key, FL.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chinaberry 953 at Midnight Cove Siesta Key, FL., vacation rental in Siesta Key

Chinaberry 953 at Midnight Cove Siesta Key, FL.

2 bedrooms
2 bathrooms
Sleeps 6
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Doveplum 624 at Midnight Cove Siesta Key, FL., vacation rental in Siesta Key

Doveplum 624 at Midnight Cove Siesta Key, FL.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Buttonwood 462 at Midnight Cove Siesta Key, FL., vacation rental in Siesta Key

Buttonwood 462 at Midnight Cove Siesta Key, FL.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun, vacation rental in Siesta Key

Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun

1 bedroom
1 bathroom
Sleeps 4
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Newly renovated condo with premium features on Siesta Key, vacation rental in Siesta Key

Newly renovated condo with premium features on Siesta Key

2 bedrooms
2 bathrooms
Sleeps 6
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Frequently Asked Questions about Siesta Key





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.
More
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.