Luxury rentals in Sarasota Beach

5.0 out of 5 average rating, 14 reviews

Experience the Ultimate in Coastal Luxury

Exclusive Amenities Include: • Private Heated Plunge Pool, Baja Shelf and Whirlpool • Pool Views on 2nd & 3rd Story Balconies • Roof top patio • Less Than 1 mile to Crescent Village • Less Than a 2 Minute Walk to Crescent Beach & Point of Rocks • Just a Short Drive to Siesta Key Village & Siesta Key Beach • Ping Pong Table / Air Hockey Table • Outdoor Lounge Areas • 8 Bedrooms, 8.5 Full Baths with Luxury Towels & Bed Linens provided • Spacious Balconies With Seating Area • Full Gourmet Kitchen

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An aerial view captures a distinctive Lazy River-style pool meandering through lush green landscaping. Surrounded by palm trees, the pool is paired with spacious lounging areas featuring sunbeds. A raised deck provides an alternative vantage point over the serene setting.

5.0 out of 5 average rating, 6 reviews

Experience Luxury at Go with the Flow! Lazy River

Go with the Flow by Exclusive Vacations Vacation Rental License #VR24-000026 Welcome to Go with the Flow, an exceptional three-level luxury retreat offering five bedrooms and five and a half bathrooms, thoughtfully designed for an elevated Anna Maria Island getaway. Located just a short five-minute stroll to Anna Maria Beach, this newly built vacation home showcases a private pool with spa, a rooftop entertainment deck, and beautifully curated designer interiors. Whether gathering with family

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The four-story home is surrounded by lush greenery, featuring a private pool with lounge chairs positioned nearby. Balconies overlook the pool area, inviting relaxation. The exterior design highlights large windows, allowing natural light to brighten the living spaces.

4.76 out of 5 average rating, 25 reviews

Seconds from the beach! Pool, Games-Ocean Overlook

Ocean Overlook by Siesta Key Luxury Rental Properties Ocean Overlook by Siesta Key Luxury Rental Properties is an exceptional eight bedroom, eight bathroom coastal retreat with two additional half baths, thoughtfully designed for large families and large group getaways seeking luxury coastal living. Located just a three-minute walk to Siesta Key Beach, this four-story Siesta Key luxury rental offers sweeping Gulf views, large balconies, and a private outdoor oasis. Guests are also a short

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An aerial view of a modern, multi-level vacation rental surrounded by lush greenery and palm trees. A private heated pool is visible in the backyard, along with a spiral staircase leading to the roof. The Gulf of Mexico can be seen in the background.

4.94 out of 5 average rating, 34 reviews

400ft to Beach, Ocean View, Pool, in the Village

Siesta Key Dream’s largest and most luxurious vacation rental, features four levels, totaling 6-bedrooms, 9-beds, & 6 full-bathrooms. Notable attributes include: a heated-pool, hot tub, 2-balconies, a roof-top sundeck, parking, a backyard and an elevator. With a premier location, beach access point #4 is 400 feet away, and the Siesta Key Village is one block away. In addition to a highly desired location, the unique property design allows beach and Gulf of Mexico views from multiple levels.

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4.69 out of 5 average rating, 13 reviews

Modern Home + Heated Pool + Spa +Walkable Downtown

NEW elegant and modern pool home in the heart of downtown Sarasota. A short walk to downtown's award-winning restaurants, shopping, marina and nightlife. Minutes drive from the world-famous white sand beaches of Siesta and Lido keys. Next to the Legacy Trail and Payne Park for biking, hiking, cafe and skate park. This professionally designed home is a fully equipped, family-friendly 5-bedroom/3.5 bath with private pool, hot tub, outdoor kitchen, office and pool table. Cert# 26-VR-000092

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5.0 out of 5 average rating, 17 reviews

Home in Arlington Park

House of Agape | Modern Luxury Escape w/ Pool

BNB Breeze Presents: House of Agape! A modern Sarasota retreat crafted for Pure Luxury. Designed with love, this golden oasis offers a private pool, sleek contemporary décor, a premium Jura coffee bar, and a fully equipped garage gym. Top amenities elevate this beautiful property even more: • Private Saltwater Heated Pool - heated at NO extra cost from Nov 21 - April 1st. • Modern Luxury Space • Professionally Designed and Furnished • Gym Set Up • Outdoor Dining Space • Beach Supplies

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5.0 out of 5 average rating, 23 reviews

New Listing! Beachfront! 2 Masters w/Ocean Views!

The Diamond Star on Anna Maria Island, a beautifully remodeled beachfront home originally built by legendary pitcher Warren Spahn. Enjoy spectacular beachfront views, white sandy shores, and unforgettable sunsets. The house features two master suites, a living room, and a kitchen, all offering magnificent ocean views. Enjoy the private decks, direct beach access, beach gear including kayaks, paddleboards, and more. After a day in the sun, relax with a cocktail in the private pool.

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5.0 out of 5 average rating, 13 reviews

#1 Rooftop Gulf Views-Theatre Room-Unmatched Slide

Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway.

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4.95 out of 5 average rating, 110 reviews

Tripletail -Beachfront - Pool & Spa - 4 King Beds-

Private Beachfront Home - one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or rent a golf cart to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king bedroom and bathroom, open floor plan kitchen , dining and family room. Upstairs are two more King bedrooms and bathrooms as well as a sitting area. Heated pool and hot tub

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A sparkling screened pool surrounded by a spacious patio area features lounge chairs for relaxation. The pool area is complemented by a hot tub and offers views of the indoor living space through large glass doors, enhancing the indoor-outdoor connection.

4.94 out of 5 average rating, 36 reviews

Screened Pool Courtyard • Hot Tub • Beach Nearby

Immerse yourself in the elegance of modern living at this stunning contemporary home, designed with sophistication in mind. Perfect for families, couples, and business travelers, this property is your gateway to Sarasota's best - from the sun-kissed shores of Siesta Key Beach to the vibrant streets of downtown Sarasota. Embrace the luxury within and the adventures that lie just beyond. Discover more below!

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4.94 out of 5 average rating, 33 reviews

Siesta Bliss ~ Luxury Waterfront Retreat

Siesta Bliss is a new 4BR/4.5BA luxury waterfront home just minutes from Siesta Key Beach 🏖️. Enjoy a private pool with waterslide, spa & sun shelf, outdoor dining, BBQ, ping pong, and stylish coastal interiors. Each bedroom has an ensuite bath, and the chef’s kitchen and bar area make entertaining easy. Perfect for relaxing beachside escapes with family and friends 🌊✨.

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4.89 out of 5 average rating, 19 reviews

Between the Waves - Siesta Key Luxury Home

Welcome to Between the Waves, a beautifully designed new construction vacation rental perfect for larger families or groups seeking a memorable getaway. With eight spacious bedrooms and 8.5 bathrooms, this upscale home is located just steps from the pristine beaches of Siesta Key and Siesta Key Village, which offers fun dining and shopping for all ages.

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Popular amenities for Sarasota Beach luxury holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great luxury holiday rentals in Sarasota Beach

5.0 out of 5 average rating, 16 reviews

Luxury Beachfront House in Anna Maria!

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4.96 out of 5 average rating, 23 reviews

60ft. Water Slide - Golf Simulator - Mini Golf

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5.0 out of 5 average rating, 14 reviews

Home in Holmes Beach

The Palace ~ Walk to Beach/Rooftop Views

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A beautifully designed pool area is presented, featuring a tear drop shaped heated saltwater pool with bubbling spouts. Expansive views of the sunset over the Gulf of Mexico are captured, complemented by lounge chairs and manicured green space nearby.

4.88 out of 5 average rating, 8 reviews

Beachfront Luxury - Resort Pool - Steps to Village

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5.0 out of 5 average rating, 7 reviews

Golf Sim-Rock Climbing Wall-Waterslide-Gulf Views

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5.0 out of 5 average rating, 12 reviews

Home in Lido Key

Gulf Views. Walk to St Armands+Beach. Pool+Slide

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5.0 out of 5 average rating, 13 reviews

Home in Lido Key

Walk to beautiful St. Armands/Beach-Pool w/Slide

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