Siesta Key Vacation Rentals

(169 rentals)
Closest Condo to the Gulf of Mexico on Siesta Key - Direct Oceanfront

Closest Condo to the Gulf of Mexico on Siesta Key - Direct Oceanfront

2 BR | 2 BA | Sleeps 6 | Quick View

3

$164

per night

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"Village Resort" 320 Canal Rd.

$151

per night

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Beach front property on #1 voted beach in America,walk to shops and restaurants

Beach front property on #1 voted beach in America,walk to shops and restaurants

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: 10% off "Summer Special" discount on any one week booking from 6 -2 to 6/23.

$163

per night

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Siesta Key Beachfront Condo with Gulf View!

$135

per night

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"Village Resort" 316 Canal Rd.

$151

per night

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Siesta Key Luxury Condo 2/2, Pools, Tennis, Gym, walk to beach.

Siesta Key Luxury Condo 2/2, Pools, Tennis, Gym, walk to beach.

2 BR | 2 BA | Sleeps 6 | Quick View

$150

per night

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*All New Villa* #1 Beach USA~ Gulfside Condo - Siesta Key

$149

per night

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BEAUTY ON THE BEACH at Crescent Arms

$150

per night

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"Peaceful Waters" ON THE DOCK" 6151 Midnight Pass Rd.

$89

per night

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"Village Resort" 318 Canal Rd.

$151

per night

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SANDPIPER

SANDPIPER

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: 10% off " Summer Special" on any 1 week booking from 7/14 to 8/7.

$115

per night

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Modernized Direct Waterfront Condo 2BR, 2B,HDTV, WIFI, Washer/Dryer, Gulf Lanai

$164

per night

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A special SECRET retreat...#26

$128

per night

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Fishermans Cove A102 - On Turtle Beach on Siesta Key

$164

per night

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Beach, Village, Canal, Private Dock & Heated Pool... No Car Needed!

$350

per night

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"Menorca" 378 Canal Rd.

"Menorca" 378 Canal Rd.

0 BR | 1 BA | Sleeps 2 | Quick View

$81

per night

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"Everglades" 378 Canal Rd.

"Everglades" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

$143

per night

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Stay in remodeled beautiful condo, walk to Siesta Key Beach! "2 weeks minimum"

Stay in remodeled beautiful condo, walk to Siesta Key Beach! "2 weeks minimum"

2 BR | 2 BA | Sleeps 4 | Quick View

$90

per night

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"Fiji" 378 Canal Rd.

"Fiji" 378 Canal Rd.

1 BR | 1 BA | Sleeps 4 | Quick View

$97

per night

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"Tropical Tree House" 6151 Midnight Pass Rd.

$81

per night

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Dolphin" 378 Canal Rd. Just a short walk to the beach and Village

Dolphin" 378 Canal Rd. Just a short walk to the beach and Village

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: "SUMMER SPECIAL" 10% discount when Booking one week Saturday to Saturday from 5/26 to 6/15

$103

per night

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Stroll the Beach....Siesta Palms by the Beach #1D

Stroll the Beach....Siesta Palms by the Beach #1D

1 BR | 1 BA | Sleeps 4 | Quick View

1

$200

per night

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Renovated 2 Bdrm/2 BA, Ground Floor with W/D, WIFI

Renovated 2 Bdrm/2 BA, Ground Floor with W/D, WIFI

2 BR | 2 BA | Sleeps 4 | Quick View

$121

per night

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SIESTA KEY HEAVEN

SIESTA KEY HEAVEN

2 BR | 2 BA | Sleeps 4 | Quick View

$171

per night

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MAGNOLIA 317-319

MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

Owner special: 10% off " Summer Special" on any 1 week booking from 6/2 to 6/16, or 7/14 to 8/11.

$151

per night

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Siesta Key - Another Day In Paradise

$215

per night

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"Village Resort" 322 Canal Rd.

$151

per night

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Top Floor Oceanfront View Of The #1 Beach In The USA! - Beautiful Decor!

Inquire for rates

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SIESTA KEY DIRECT GULF FRONT CLEAN/NEAT WKLY RENTALS SECURE WEB

$243

per night

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Luxurious 3 Bedroom on Siesta Key Beach

$260

per night

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"Key West" 378 Canal Rd.

"Key West" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

$151

per night

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"SITTING ON THE DOCK OF THE BAY" "Coastal Courtyard" 6151 Midnight Pass Rd.

$77

per night

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Best Location - Resort Amenities - Walk to Beach and Village, Pool & Boat Docks

$110

per night

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The Solaster

The Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

$396

per night

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steps from the siesta key Beach

steps from the siesta key Beach

2 BR | 2.5 BA | Sleeps 6 | Quick View

$156

per night

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Breathtaking Beachfront Siesta Key Rental: Now Available Aug, Sept & Oct

Breathtaking Beachfront Siesta Key Rental: Now Available Aug, Sept & Oct

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: 10% OFF Weekly Stays in September!

$171

per night

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Paradise Awaits! 2br Siesta Palms by the Beach #2B

$265

per night

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The Water is Great! Siesta Key Inn #125

$186

per night

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Charming! Siesta Palms by the Beach #1A

$214

per night

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Hanging at the Beach House! Siesta Key Inn #224

$186

per night

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Unique Boutique! 3 br Siesta Key Inn #223

$459

per night

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Beach, Beach, Beach! 1 BR Siesta Palms #2D

Beach, Beach, Beach! 1 BR Siesta Palms #2D

1 BR | 1 BA | Sleeps 4 | Quick View

$200

per night

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Enchanting! Siesta Key Inn #126

$186

per night

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Tropical Oasis! 1 Br Siesta Key Inn #123

$186

per night

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Beach Time! - 2Br/2B Siesta Key Inn #225

$265

per night

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Sunny Fun! 1 Br Siesta Palms by the Beach #2A

Sunny Fun! 1 Br Siesta Palms by the Beach #2A

1 BR | 1 BA | Sleeps 4 | Quick View

$214

per night

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Sweet Island Beauty! Siesta Key Inn #124

$186

per night

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Sweet Tranquility! Siesta Palms By Beach #1B

$299

per night

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Prestigious BEACHFRONT Complex. Updated Condo 1640 sq ft. $3,700/mo MAY-NOVEMBER

Prestigious BEACHFRONT Complex. Updated Condo 1640 sq ft. $3,700/mo MAY-NOVEMBER

2 BR | 2 BA | Sleeps 4 | Quick View

$123

per night

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Tropical Escape 2 Br/2 B Siesta Key Inn #226

$265

per night

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Local Weather

 | 

71°  51°
JANUARY
Ocean 64°
74°  54°
FEBRUARY
Ocean 65°
77°  58°
MARCH
Ocean 67°
81°  62°
APRIL
Ocean 73°
86°  68°
MAY
Ocean 78°
89°  73°
JUNE
Ocean 82°
91°  74°
JULY
Ocean 85°
91°  75°
AUGUST
Ocean 87°
89°  73°
SEPTEMBER
Ocean 85°
85°  67°
OCTOBER
Ocean 82°
79°  60°
NOVEMBER
Ocean 75°
74°  54°
DECEMBER
Ocean 69°

Siesta Key condo rentals in gulf coast Florida's top barrier island

Siesta Key is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida. It’s known for its sandy beaches and friendly locals. Fine white sand and gentle gulf breezes keep visitors coming back year after year. An ideal escape for a couple looking for romance, or a family looking to escape the Disney or Panama City crowds.

Siesta Key has amazing beach front with available rentals for you. When staying in one of our Siesta Key vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Use the filters to narrow down your choices and choose the rental that calls to you.

Climate

Prevalent sunshine and gentle coastal breezes should be expected daily. Sounds incredible, right? Well, it is. With well over 300 sunny days per year, you’d be hard pressed to visit Siesta Key at a “bad time”. Low humidity makes the area comfortable, as well as warm. Bring your sunblock to protect against UV rays and don’t forget a few pairs of swim trunks, as the warm gulf waters are perfect for boogie boarding and bodysurfing.

Getting around

From November to September the Siesta Key Trolley will take you from the southernmost part of the island to the north end. The 3 open air trolleys run 7 days a week from 8-Midnight between Turtle Beach to Siesta Village. They will pass by about every 20-30 minutes. So don’t worry too much about getting around this small barrier island. Plus, bike or scooter rentals are everywhere -- so you can exercise while you move from beach to beach.

For those who drive, two bridges link the island to the mainland. The north bridge, Siesta Drive, is within the City of Sarasota and provides convenient access to the city, its business and arts districts, and to the Sarasota/Bradenton International Airport via US Highway 41. The south bridge, Stickney Point Road, provides access to south Sarasota County and a direct route to Interstate 75.

Top activities and attractions

Let’s be serious: you’re visiting Siesta Key for the pristine beaches along the 35 miles of coastline. Here are the names to remember: Siesta Beach, Turtle Beach, and Crescent Beach. Each features soft quartz sand and warm gulf seas. The sand is cool on your feet, so you can take an extended walk by the ocean without fear.

Siesta Beach has relatively shallow waters and it is monitored by lifeguards year-round. Plus, there’s plenty of room to spread out and enjoy a long, relaxing day. Turtle Beach is the most active (think volleyball net and horseshoe pits) while Crescent Beach is known for its seclusion and relaxed atmosphere.

Just off the southern tip of Crescent Beach is Point of Rocks, one of the best places for snorkeling and underwater exploration along the Gulf Coast beaches. It is made up of large chunks of limestone covered with coral and sponges and a range of sea life inhabit these underwater formations.

Bring your clubs here, too. With over 100 golf courses in the area you’ll want to take advantage of the sunny days out on the links. There’s ample opportunity for water sports for those who shun dry land. Visitors can find companies offering kayaking, paddle boarding, deep sea fishing and much more.

Just north of Siesta Beach, Siesta Key Village has many stores ranging from hip and funky to high-end boutiques and, of course, we wouldn't be a beach town without the beach accessory and souvenir shops.

Events 

If you love carefully constructed creations, visit in May for the sand castle competition. Local sand artisans and amateurs try their hand at creating jaw-dropping scenery out of sand.

Every Sunday there’s the Drum Circle featuring a cacophony of sound from various instruments performed by locals and tourists. Enjoy a stroll through the galleries of Palm Avenue on the first Friday of every month. In addition to fine galleries, this area along lower Main Street is known for its unique variety of shops and restaurants.

In April, the aptly named Siesta Fiesta takes place. Stroll along the beach while enjoying fine art and handmade crafts from 200 of the nation’s most talented artists and crafters. Showcasing an extensive collection of work ranging from life-size sculptures, spectacular paintings, one-of-a-kind jewels, photography, ceramics and more, this show truly has something for anyone. Complete with an additional green market, this spectacular show also features plants, body products, and tasty dips.

Siesta Key house rentals on FloridaRentals.com

Booking a condo for rent in Siesta Key on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!