Beach house vacation rentals in Siesta Key

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Top-rated beach house rentals in Siesta Key

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Guest favorite

A cozy living area features a sectional sofa adorned with yellow cushions. A central coffee table sits on a patterned rug, surrounded by floor cushions in bold colors. Bright natural light filters through the windows, enhancing the inviting atmosphere.

Home in Sarasota

4.95 out of 5 average rating, 22 reviews

Siesta Key Oasis 8 minutes to Beach Kg; Qn FL Room

3-Bdr family friendly on a quiet street in subdivision closests to Siesta Beach with one King, one Queen, and two Full beds, and spacious living area. 8 minutes to Siesta Key Beach. RecRoom with a Queen Sleeper and office. One car garage. Fenced in large private backyard, and patio. Located near renowned beaches, parks, gardens, biking trails, and golf. Costco, Publix less than half a mile away. Please inquire about parking Boat, RV or trailer in driveway - can accommodate up to certain sizes.

Top guest favorite

An airy dining area features a glass table supported by a unique wooden base, surrounded by four woven chairs. Natural light floods the open space, highlighting the modern kitchen with white cabinetry and high-end finishes, while a large pendant light adds a stylish touch.

Home in Siesta Key

4.99 out of 5 average rating, 80 reviews

Relax in a Private Tropical Retreat on Siesta Key!

Your dream vacation awaits with a renovated, spacious, and private single-level house. It's a perfect getaway for a relaxing vacation! Enjoy all the comforts of home while being just a short walk away from restaurants, bars, and Siesta Key's beautiful white sand beaches. Nestled on a quiet tree-lined street and tropical gardens, this retreat offers tranquility and serenity. The community boasts a large heated pool and intercoastal waterway pier, ideal for afternoon fishing or sunset beverages!

Guest favorite

The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.

Home in Sarasota

4.88 out of 5 average rating, 157 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

Superhost

A serene outdoor space features a heated pool surrounded by lounging areas, including a table and chairs. Lush greenery and palms provide privacy, while views of the canal add to the tranquility. A patio umbrella offers shade near the seating area.

Home in Siesta Key

4.91 out of 5 average rating, 23 reviews

Siesta Key Hideway -3 bedroom canal pool home

Take a moment to enjoy the quiet side of Siesta Key. This home sits on a tree canopied street and offers a rare and serene location along with 3 large bedrooms and open plan living and dining. Cook in the gorgeous kitchen while looking out over the mangrove lined canal. Walk through the neighborhood , spend time on the patio or in the pool and take in the calm beauty that this home offers. All of this lies a short distance from the beach, Siesta Village, Sarasota and surrounding areas.

A three-story waterfront home is showcased beside a tranquil canal, framed by palm trees. The light blue exterior features multiple balconies, providing scenic views. Lush green grass leads to the water's edge, enhancing the inviting outdoor space.

Home in Anna Maria

4.75 out of 5 average rating, 28 reviews

Waterfront Home with Pool and Spa! - AM I Dreaming

AM I Dreaming by AMI Locals Home in Anna Maria VR19-000055 Welcome to AM I Dreaming, a luxurious three bedrooms and three and a half bathroom waterfront home that offers the perfect blend of canal and beach living with premium amenities to ensure a fantastic stay! The resort-style patio beckons with a luxurious saltwater pool and spa, an inviting outdoor dining area, and a convenient launch spot for kayaks and paddleboards, promising the ultimate blend of tranquility and excitement.

A well-maintained exterior showcases a stone pathway leading to the entrance, framed by lush greenery and palm trees. The home is surrounded by manicured landscaping featuring artificial grass and gravel pathways, creating a welcoming outdoor space.

Home in Siesta Key

5 out of 5 average rating, 3 reviews

Charm Beach House

🌴 Coastal Bliss in Siesta Key – Your Beach Escape Awaits! 🌊 Escape to paradise just minutes from Siesta Key Beach, consistently ranked the #1 beach in America and even #4 worldwide for its powdery white quartz sand and stunning turquoise waters. Whether you're seeking sun-soaked relaxation or an adventure-filled getaway, our charming retreat is your ideal home base. Enjoy a cozy, spacious, fully equipped home designed for comfort and ease. Perfect for couples, families, and groups.

Top guest favorite

A tropical backyard features a heated saltwater pool surrounded by palm trees and vibrant landscaping. Lounge chairs are arranged beside the pool, and an outdoor covered seating area with colorful chairs provides a relaxing retreat. A light-colored home stands in the background.

Home in Holmes Beach

4.97 out of 5 average rating, 32 reviews

Loggerhead - AMI Oasis w/ Private Pool + Golf Cart

Loggerhead is back and ready to welcome you! ️ Escape to the tranquility of Anna Maria Island in this charming 2-bedroom, 2-bathroom home nestled on a peaceful, secluded street. Relax in your private tropical backyard featuring a heated saltwater pool. You'll never need to worry about parking just steps from the beach, about a 4 minute walk. We provide everything for your getaway including beach essentials and a 6-person street-legal golf cart. Your perfect family paradise awaits!

Superhost

A private pool area is featured, surrounded by tropical landscaping. A shallow tanning ledge is visible, alongside a swim-up bar table with stools. Two thatched umbrellas provide shade over matching lounge chairs. Decorative bronze herons create a water feature, enhancing the tranquil ambiance.

Home in Anna Maria

4.9 out of 5 average rating, 20 reviews

Beach N Bay 206 by Duncan Real Estate

Welcome to Beach N Bay 206! Pool COOLING for hot summer days! A honeymooners delight or a couple's retreat! Enjoy a romantic getaway! Don't miss your chance to stay at the North end of Anna Maria Island in the highly desirable village of Anna Maria, one of Coastal Living Magazine's Top 10 Happiest Seaside Towns! Located right in the middle of all that happiness, Beach N Bay is the island vacation cottage duplex that's so tropical and fun, you'll swear you can hear steel drums!

Top guest favorite

The property is surrounded by lush greenery, featuring a spacious driveway leading to a single-story home. Tall palm trees and various plants are visible in the yard, creating a tropical ambiance. The structure is situated in a serene neighborhood, showcasing nature's beauty.

Home in Osprey

4.96 out of 5 average rating, 47 reviews

Creekside Paradise I

The 1970 sqft living space hosts 3 bedrooms, 2 bathrooms, an open living room with attached ‘library’, a dining area, as well as a fully equipped kitchen. From the caged pool area you have a view of the North Creek and our Boat Dock. The pool can be electrically heated and measures 32.80ft in length/13.12ft in width. You enter Creekside Paradise I thru the attached 2 car garage, where you can find the beach equipment (chairs, umbrella, cooler).

Guest favorite

A spacious living area features a modern sectional sofa adorned with decorative pillows. Natural light filters through large windows with light curtains, illuminating soft, neutral tones in the decor. A coffee table sits in the center, accompanied by a wall-mounted decorative piece.

Home in Venice

4.94 out of 5 average rating, 83 reviews

Venice 3BR/2BA*8 min Beach*Baby Gear*Air Hockey*

Modern house in Venice, 8 minutes drive to the beach, close to restaurants, and shops. Situated in a serene and relaxing neighborhood with completely fences backyard. Bicycles, beach stuff, outdoor gas grill, and beach towels are available. Plenty of nearby beaches to choose from. Late check out fee applied past 10 am. No smoking allowed, $500 fee will apply. Sorry no pets (service or emotional) are allowed due to Host allergies.

Top guest favorite

A stylish chaise sofa in vibrant blue is positioned next to a wooden crate filled with records, showcasing a collection of vintage albums. Soft natural light filters through the nearby window, highlighting the textured area rug and the decorative artwork on the wall.

Home in Venice

5 out of 5 average rating, 42 reviews

Lovely Dog-Friendly Oasis ~ Walk to Beach ~ Office

Look no further than the lovely 3BR 1Bath gem, ideally nestled in the tranquil neighborhood just a few blocks from the peaceful and picturesque Golden Beach. Explore the stunning natural attractions and landmarks before retreating to a relaxing, entertaining home with stylish details, modern amenities, and inviting outdoors. Golden Beach .3 miles Sharky's Pier 1.2 miles Brohard Paw Park 1.3 miles

Superhost

Home in Siesta Key

5 out of 5 average rating, 5 reviews

Fully Remodeled Siesta Water Front Private Villa

*This property has been Fully Remodeled and is accepting reservations following the 2024 Hurricanes.* Ease into the modern styling of the beautifully furnished stand-alone home, Villa Krystal. Located directly on Siesta Keys inter-coastal waterway in the highly desirable Polynesian Gardens neighborhood, Villa Krystal promises to bring you luxury stylings, amenities, comfort, and convenience.