Siesta Key Vacation Rentals

(78 rentals)
Goldeneye Luxury Private Home, Pool,All Day Sun, free WiFi cable ,bikes

$336

per night

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

$140

per night

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SIESTA KEY WATERFRONT HOME with gorgeous water views and boat dock!

SIESTA KEY WATERFRONT HOME with gorgeous water views and boat dock!

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.5 miles to Turtle Beach

$185

per night

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SIESTA KEY #1 US BEACH, HOUSE OF GLASS. A PLACE TO CALL HOME.

SIESTA KEY #1 US BEACH, HOUSE OF GLASS. A PLACE TO CALL HOME.

4 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.9 miles to Siesta Key white quartz sand...sugary white.

$214

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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Fishermans Cove A102 - On Turtle Beach on Siesta Key

$164

per night

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The Solaster

The Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

$536

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

$150

per night

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Siesta Key Beachfront Condo with Gulf View!

$135

per night

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Condo on Private Beach in siesta key monthly rental only

$224

per night

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Beautiful Siesta Key Beach Condo - GREAT LOCATION!!

$152

per night

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Couples and Family Friendly. Some pet friendly units are available too.

Couples and Family Friendly. Some pet friendly units are available too.

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 20 yards to Siesta Key Beach

$171

per night

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BEST VILLA ON SIESTA KEY

BEST VILLA ON SIESTA KEY

2 BR | 2 BA | Sleeps 6 | Quick View

$148

per night

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Gulf Front with amazing sunsets and Free Boat Dock

$164

per night

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Sandy's Siesta!! Total remodel!! NO DAMAGE FROM HURRICANE IRMA!!

Sandy's Siesta!! Total remodel!! NO DAMAGE FROM HURRICANE IRMA!!

2 BR | 1.5 BA | Sleeps 4 | Quick View

Distance to beach: 200 yards to Crescent Siesta Key Beach

$125

per night

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Ground Floor 550sqft 1BR Condo Siesta Key Crescent Beach + WiFi No Road to Cross

Ground Floor 550sqft 1BR Condo Siesta Key Crescent Beach + WiFi No Road to Cross

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 250 yards to Siesta Key Crescent Beach

$86

per night

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Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach

$495

per night

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Fishermans Cove A302

Fishermans Cove A302

2 BR | 2 BA | Sleeps 6 | Quick View

$164

per night

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Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa

$395

per night

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Siesta Key Beachfront 3 Bedroom Private Home

Siesta Key Beachfront 3 Bedroom Private Home

3 BR | 3 BA | Sleeps 7 | Quick View

Distance to beach: 300 feet to Siesta Beach

$564

per night

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Large 1300sqft 2BR2BA 4th Floor Siesta Key Crescent Beach WiFi No Road to Cross

Large 1300sqft 2BR2BA 4th Floor Siesta Key Crescent Beach WiFi No Road to Cross

2 BR | 2 BA | Sleeps 5 | Quick View

2

Distance to beach: 100 yards to Siesta Key Crescent Beach

$156

per night

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DEAL
2BR2BA 2nd Floor 800sqft Condo Siesta Key Crescent Beach + WiFi No Road to Cross

2BR2BA 2nd Floor 800sqft Condo Siesta Key Crescent Beach + WiFi No Road to Cross

2 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 120 yards to Siesta Key Crescent Beach

$100

per night

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DEAL
Siesta Key, Heated pool, Gulf/Bay Siesta Key, Gated, freshly renovated

$122

per night

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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

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

$164

per night

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A special SECRET retreat...#26

$128

per night

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Tropical Escape 1 Br Siesta Key Inn

$186

per night

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DEAL
Sea Wave Casita

Sea Wave Casita

2 BR | 2 BA | Sleeps 6 | Quick View

$146

per night

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Monarch Villa

Monarch Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$171

per night

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Casa Stolida

Casa Stolida

4 BR | 3 BA | Sleeps 8 | Quick View

$257

per night

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Casita Coco

Casita Coco

1 BR | 1 BA | Sleeps 4 | Quick View

$86

per night

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The Palms Cottage

The Palms Cottage

4 BR | 2 BA | Sleeps 10 | Quick View

$179

per night

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Sophie’s Quartier

Sophie’s Quartier

6 BR | 5 BA | Sleeps 16 | Quick View

$443

per night

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Sandy Cabana

Sandy Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$171

per night

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Casa Costero

Casa Costero

3 BR | 3 BA | Sleeps 9 | Quick View

$171

per night

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Casita Blanca

Casita Blanca

2 BR | 1 BA | Sleeps 4 | Quick View

$129

per night

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CocoBayou Cottage

CocoBayou Cottage

3 BR | 2 BA | Sleeps 10 | Quick View

$171

per night

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Casita Bayou

Casita Bayou

2 BR | 1 BA | Sleeps 6 | Quick View

$129

per night

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Seahorse Cabana

Seahorse Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$171

per night

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Gorgeous Condo directly on #1 Beach in USA - #111

Gorgeous Condo directly on #1 Beach in USA - #111

1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 150 yards to Crescent Beach

$201

per night

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The Grand Canal Cottage

The Grand Canal Cottage

5 BR | 4 BA | Sleeps 12 | Quick View

$429

per night

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Honey Mango Cabana

Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$121

per night

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Sea the View

Sea the View

4 BR | 3 BA | Sleeps 10 | Quick View

$214

per night

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Pura Vida Oasis

Pura Vida Oasis

5 BR | 3 BA | Sleeps 13 | Quick View

$200

per night

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Serenity Cottage

Serenity Cottage

3 BR | 3.5 BA | Sleeps 8 | Quick View

$171

per night

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Siesta Key Village Condo - 2 BR 2 BATH with Pool

Siesta Key Village Condo - 2 BR 2 BATH with Pool

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.1 miles to Siesta Beach

$143

per night

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Island Sol

Island Sol

5 BR | 4 BA | Sleeps 14 | Quick View

$250

per night

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Casa Ohana

Casa Ohana

4 BR | 3 BA | Sleeps 12 | Quick View

$257

per night

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Casita Playa

Casita Playa

2 BR | 1 BA | Sleeps 4 | Quick View

$129

per night

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Seaside Cottage

Seaside Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

$286

per night

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Sol y Mar

Sol y Mar

4 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

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Stay in a rental on gulf coast Florida’s top barrier island, Siesta Key

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 a rental 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.

Siesta Key Climate

Prevalent sunshine and gentle coastal breezes should be expected daily in Siesta Key. 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 Siesta Key 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 Siesta Key

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 in Siesta Key

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 in Siesta Key

If you love carefully constructed creations, visit Siesta Key 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 Siesta Key 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.

Why you should book a Siesta Key home on FloridaRentals.com

Booking an Siesta Key vacation rental or seaside condo 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!