Top 14 Vacation Rentals in Siesta Key, Florida

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Located just south of the city of Sarasota, Siesta Key is famous for its pristine beaches, made up of 99 percent quartz sand and edged by dazzling aquamarine Gulf Coast waters. Siesta Key Beach is often named the very best in the entire country and you’ll find many vacation rentals that provide easy access to the sands, some of which are beachfront. For the best of the best, consider booking one of these with options that include everything from condos to private homes and even a palace.

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Beachfront Getaway in Siesta Key
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Beachfront Getaway in Siesta Key

Beachfront Getaway in Siesta Key

When you stay at this top beachfront vacation rental in Florida, you’ll be just steps from your own private stretch of sand on America’s most beautiful beach. There’s a private seating area along the beachfront with a grill, lounge chairs, a cabana, and picnic tables as well as a year-round heated pool. A one-story townhouse, it accommodates up to four guests and includes a modern kitchen, two flat-screen cable TVs, a washer/dryer, and a luxurious bedroom.

Siesta Beach House
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Siesta Beach House

Siesta Beach House

Just 200 feet from world-famous Siesta Beach and its whiter than white sands and a one-minute drive to the shops and restaurants in Siesta Village, this two-bedroom home accommodates up to five guests. Enjoy a tranquil getaway that includes a swimming pool and all the conveniences you’re looking for, including a full kitchen, cable TV, washer and dryer. The porch has an area for dining alfresco and you’ll have beach equipment, pool toys, and access to a SUP rental.

Shark Top Village Walk to Beach
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Shark Top Village Walk to Beach

Shark Top Village Walk to Beach

Located right across the street from the beach close to everything, including shopping and dining, this three-bedroom rental is ideal for a large family, accommodating up to 12. It sits on the first floor as part of a duplex property and has its own private entrance and outdoor entertaining area that includes a soaking pool, Jacuzzi, seating area, and BBQ grill, along with some impressive, colorful works of art. You’ll have a full kitchen, cable TV, washer/dryer, and even an arcade game too.

5th Floor Condo on Crescent Beach with 180-Degree Panoramic Views
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Siesta Key 5th Floor Condo – Siesta Beach

5th Floor Condo on Crescent Beach with 180-Degree Panoramic Views

One of the best Vrbo vacation rentals in Florida, this 5th-floor condo sits right on Crescent Beach, providing a 180-degree view of the Gulf and glistening white sands. You’ll even be able to watch the dolphins that go by from the lanai and through the sliding glass doors that lead to the lanai in every room. The colorful sunsets from here are absolutely dreamy. It accommodates up to five guests in two bedrooms, each of which has its own bath, and cable TV with a DVD player, in addition to the view and lanai access. You’ll love cooking in the kitchen with that unobstructed Gulf view and enjoy having your own washer/dryer too. The complex includes a shared heated pool you’ll have access to as well.

Siesta Key Oceanfront Palace with Private Beach
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Siesta Key Oceanfront Palace

Siesta Key Oceanfront Palace with Private Beach

It would be hard to find a rental more luxurious than this. A direct beachfront palace that sits on nearly an acre behind private gates, you’ll have your own private beach and 9,000-square-feet of space for up to 12, with five bedrooms and seven full baths. It comes complete with a pool, hot tub, waterslide, and grotto along with a rooftop patio that has a gym and a bar. You’ll have indoor entertainment too, including a game room with foosball and pool tables.

Siesta Key SunBum Studio, On the Beach
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Siesta Key SunBum Studio, On the Beach

Siesta Key SunBum Studio, On the Beach

Located at the Palm Bay Club, guests who stay at this studio condo will be on the ground level just steps from a private white sandy beach and the sparkling Gulf waters. You can enjoy a myriad of amenities at this popular Airbnb on Florida’s Gulf Coast, like two swimming pools, a hot tub, a fishing pier, a gym, tennis courts, and BBQ grills. Two free bikes are included for easy exploring too. After a day of fun, you can enjoy the stunning views from floor-to-ceiling windows inside or from the shared lanai which has an outdoor teak patio set for dining. A Smart TV and kitchenette with a Keurig coffee machine, microwave, and mini-fridge are included too.

Sunspot Cottage Getaway
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Sunspot Cottage Getaway

Sunspot Cottage Getaway

This cheery yellow cottage sits on a nearly four-acre property with other private cottages, tucked among oak, palm, and banyan trees. You’ll have access to a wealth of amenities, including a swimming pool, a fishing pier, and a picnic/BBQ area with grills. Beach toys, a cart, towels, and pool toys are all supplied, while Crescent Beach and incredible sunsets over the Gulf of Mexico can be enjoyed with just a short walk. A full kitchen with a dishwasher, cable TV, Wi-Fi, and a washer/dryer are all included too.

Renovated Modern Ranch with Pool, Spa & Private Back Yard
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mid-century pool at Renovated Modern Ranch House

Renovated Modern Ranch with Pool, Spa & Private Back Yard

A custom mid-century modern three-bedroom for up to six guests, stay here and you’ll have your own private pool nestled among native greenery and loungers for soaking up the sun. You’ll be just 15 minutes from the powdery quartz sand at Siesta Key beach access 8 where you might spend the day and then come back to enjoy the pool with its custom lighting after dark. You’ll have a luxurious kitchen with all you need to prepare gourmet meals, a BBQ grill, fire pit, and two screened lanais, one furnished for outdoor dining. Wi-fi and a Smart TV with apps for streaming are included too.

Amazing Beach Views From a Newly Renovated Condo
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Amazing Siesta Key Beach Views

Amazing Beach Views From a Newly Renovated Condo

This two-bedroom condo for up to six provides access to the beach and dazzling panoramic views from indoors or out with 50′ of floor-to-ceiling windows and two large balconies. A gulf-front corner unit, it includes a 65″ Smart TV with cable, a well-stocked kitchen with a dishwasher, and dining for six, complete with a view of the endless turquoise water. The bedrooms both have their own TVs with the master featuring an en-suite bath. Beach towels, chairs, an umbrella, cooler, and beach cart are all supplied too.

Coolest House in Siesta Key Village
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Coolest House in Siesta Key Village

Coolest House in Siesta Key Village

A two-bedroom mid-century modern home for up to five guests, this rental features Sarasota School of Architecture style indoors and out, with the beach within a 10-minute walk or 2-minute pedal using the bikes that are supplied. Snorkeling gear, an umbrella, beach blanket, and towels are all provided too. Afterward, head back and enjoy the Agnellio built pool. You’ll also have a full kitchen for making your meals and a grill for cookouts, a washer/dryer, and a TV.

Hide-A-Way Suite, Only 60 steps to Siesta Key Beach
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Hide-A-Way Suite, Siesta Key

Hide-A-Way Suite, Only 60 steps to Siesta Key Beach

A one-bedroom ground floor apartment, the Hide-A-Way Suite offers a comfortable space for up to four with a king-size bed in the bedroom and a luxury queen-size self-inflating air bed for the living room. The beach is right across the street and the host supplies beach chairs and umbrellas. When you want to head into town to enjoy the shops and eateries, it’s easily reached on foot or via the trolley stop on the corner. One of the other highlights is the French doors that open to a sunny patio that overlooks the black bottom heated waterfall pool. It’s a great space for enjoying your morning coffee or just relaxing.

Condo with Ideal Location, Siesta Key Beach Across the Street
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Ideal Location With Siesta Key Across the Street

Condo with Ideal Location, Siesta Key Beach Across the Street

A 5-star rated condo for up to four guests, this rental is just across the street from Siesta Key Beach and steps from the trolley that will take you into Siesta Key Village. You’ll have access to a marina for fishing and watching the manatees that occasionally swim by, a heated pool, and a sauna. There are picnic tables and BBQ grills for cookouts and you’ll have beach gear like oversized beach towels, chairs, an umbrella, and a beach caddy. It includes a screened-in lanai for dining and relaxing and a high-end kitchen too.

Siesta Key Quaint Beach House
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Siesta Key Quaint Beach House

Siesta Key Quaint Beach House

A 1950s beach house for up to four guests, this home will put you just five minutes on foot from Siesta Key beach. It features terrazzo floors and cypress wood floors, a 65″ HDTV, a full kitchen, BBQ grill, and outdoor dining space. A beach cart, beach toys, snorkel gear, noodles, and beach towels are supplied, plus you’ll be in a top spot for birdwatching and other wildlife viewings. Siesta Village is a two-minute shuttle or 15-minute walk away from enjoying restaurants, bars, and nightlife.

Sea Club 2 Mermaid's Rest
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Sea Club 2, Siesta Key

Sea Club 2 Mermaid's Rest

Located in Sea Club 2, the Mermaid’s Rest is a one-bedroom rental for two that comes with a ton of amenities. You’ll be across the street from a gorgeous stretch of Siesta Key beach while enjoying a heated pool, picnic area with grills, and a Tiki bar. There’s a dock if you want to try and catch your dinner too. You’ll have all the necessities from a full kitchen to a washer and dryer along with a pair of beach chairs, an umbrella, and a beach cart.

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