Vacation rentals in Siesta Key

A heated pool is surrounded by a tiled deck, with lounge chairs available for guests. Palm trees and blue umbrellas create a tropical atmosphere, while the beach and ocean are visible beyond the pool area under a clear blue sky.

4.95 out of 5 average rating, 135 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels. Washer/dryer located down the hall

A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.

4.93 out of 5 average rating, 121 reviews

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

4.99 out of 5 average rating, 199 reviews

A covered patio space is surrounded by lush greenery and decorative plants. A light-colored table and two chairs are arranged on a tiled floor. Large, double doors in a vibrant blue lead to the outdoors, enhancing the welcoming atmosphere.

Guest suite in Sarasota

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

4.93 out of 5 average rating, 118 reviews

The enclosed Lanai features large bay windows showcasing views of the Gulf of Mexico. A seating area includes wicker chairs and a coffee table. Light-colored walls are contrasted by wooden accents and a ceiling fan, creating a bright and airy atmosphere.

Apartment in Siesta Key

Siesta Premier Location - The 'Calm of Siesta'

My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.

5 out of 5 average rating, 132 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to beautiful Siesta Key, the #1 beach in the country! Gorgeous newly renovated one bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

5 out of 5 average rating, 18 reviews

Bungalow in Siesta Key

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed and private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional queen sofa-bed allows accommodations for three guests.

5 out of 5 average rating, 15 reviews

A private heated pool is surrounded by a spacious stone patio, featuring comfortable lounge chairs. Lush greenery provides a tropical backdrop, while a charming cottage with turquoise siding is visible nearby. Soft sunlight reflects on the tranquil water, enhancing the peaceful ambiance of this outdoor area.

Home in Siesta Key

Toes In The Sand | Private Pool, Walk to Beach!

🦩Exclusive Amenities Include: • Private Heated Pool • 3 Minute Walk to Siesta Key Village • 1 Minute Walk to Siesta Key Beach • Outdoor Lounge Area • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Caddy • Gas Grill • Enhanced cleaning protocols by our CottageClean Team • Island Shuttle Transportation Available • Dog Friendly (1 dog up to 25 lbs with an additional fee)

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

4.97 out of 5 average rating, 346 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

A well-appointed kitchen features light-colored cabinetry and countertops, with modern appliances including a microwave and oven. An island provides additional workspace, while a dining area is visible in the background. Soft lighting creates a welcoming ambiance throughout the space.

4.96 out of 5 average rating, 112 reviews

Palm Bay Club! Resort Style Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

A bright living area features large glass sliding doors that open to a balcony with ocean views. The space includes a cozy sofa, a sleek dining area, and a kitchen with modern appliances. Natural light fills the room, enhancing its airy feel.

4.97 out of 5 average rating, 30 reviews

Oceanview Penthouse |1-Min Walk to Beach + Terrace

Penthouse Aqualina Ocean view luxury penthouse. Breathtaking views from private 400sqft terrace! 20 steps from grounds to Americas best beach. Impeccably and fully renovated in 2023. 4-minute golf cart or free trolley ride to shopping dining and entertainment in Siesta Key Village. Travelers agree, this is the top ocean-view rental on Siesta Key! Book an escape today! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta

A living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.

4.84 out of 5 average rating, 251 reviews

Cozy 1BR Beach Condo on Siesta Key!

Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.

A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.

4.92 out of 5 average rating, 116 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

Popular amenities for Siesta Key vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Siesta Key

An open-concept living and dining area is highlighted, featuring a white dining table with six chairs, a comfortable seating arrangement, and large glass doors leading to a balcony. A neutral color palette is complemented by a decorative mirror and modern lighting.

4.98 out of 5 average rating, 58 reviews

2 BR condo in Siesta Key w/ Private beach access

5 out of 5 average rating, 15 reviews

Cottage in Siesta Key

House with pool 1 block to village, 3blks to beach

4.93 out of 5 average rating, 27 reviews

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

Home in Arlington Park

Coastal Retreat near Siesta Key Beach and Downtown

5 out of 5 average rating, 5 reviews

Condo in Sarasota

Spectacular 2B Condo on Siesta Key Beach

4.95 out of 5 average rating, 88 reviews

The exterior of a cottage features light-colored siding and a turquoise door, framed by shade from a large oak tree. The entrance is surrounded by white gravel, with lounge chairs and beach equipment visible. Bright sunlight illuminates the scene, enhancing the tropical atmosphere.

Cottage in Siesta Key

Surf Shack- Walk to Village/Boat Dock Included

A heated swimming pool is surrounded by palm trees and lounge chairs. The clear blue water reflects the bright sky, with the beach visible in the background. The pool area is designed for relaxation, featuring a gradual entrance into the water.

4.93 out of 5 average rating, 15 reviews

Jamaica Royale #11- 3 Heated Pools On The Beach!

Vacation home in Siesta Key

A vibrant sunset is captured over Siesta Key Beach, with palm trees silhouetted against the colorful sky. The horizon features a gradient of warm hues, creating a tranquil ambiance. Nearby structures are visible beneath the palms, offering a sense of proximity to the sandy shoreline.

4.99 out of 5 average rating, 103 reviews

Siesta Beach View : Pineapple Bungalow Efficiency

Gentle waves lap against a sandy beach under a partly cloudy sky. A palm tree extends its fronds towards the water, framing the serene seascape. Soft hues of pink and blue are visible in the clouds, enhancing the tranquil coastal view.