Luxury rentals in Sarasota

Luxury Beachfront House in Anna Maria!

ANNA MARIA-LOCATED JUST STEPS AWAY FROM THE BEACH AND SHOPPING! This luxury house on the bay features sweeping views of the Bay, Passage Key, Beachfront, and Skyway Bridge. With 4 bedrooms and several entertainment areas this makes an amazing retreat for a family or group of friends that have luxury tastes while enjoying the relaxed atmosphere of Anna Maria. Features include a pool and spa with a putting green and rooftop deck! This is as luxurious as it gets with a short walk to downtown shops

Hospitality · Location · Family · Outdoor spaces · Indoor spaces · Pool · Beach · Cleanliness · Walkability · View · Hot tub · Kitchen · Comfort · Nearby · Getting around · Condition · Accuracy · Pets · Grill · Checkout · Value · Check-in

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

Hospitality · Pool · Location · Accuracy · Comfort · Indoor spaces · Family · Beach · Outdoor spaces · Cleanliness · Condition · Value · Bathroom · Kitchen · Nearby · Laundry · Parking · Walkability · Getting around · View · Checkout · Check-in · Amenities

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

Hospitality · Location · Pool · Hot tub · Kitchen · Comfort · Cleanliness · Sleep quality · Decor · Beach · Quiet · Nearby · Indoor spaces · Family · Accuracy · Outdoor spaces · Check-in · Amenities

Waterfront Home Private pool, elevator and dock

Luxury waterfront retreat w/pool, spa, boat ramp & dock! Elevator makes it perfect for multi‑generational family getaways. This brand-new home features airy open-concept living and 4 bedrooms (3 primary en-suites with King). Swim in the sparkling pool, soak in the spa, grill on the BBQ, and dine under the covered patio. Just minutes to Gulf beaches and local dining. Bring your boat and enjoy waterfront living from your own backyard oasis, where you can relax and watch manatees in the canal.

Pool · Hospitality · Outdoor spaces · Beach · Comfort · Family · Hot tub · Location · Decor · Cleanliness · Walkability · Kitchen · Grill · Layout · Nearby · Indoor spaces · Access · Accuracy · Bathroom · Quiet · Laundry · Getting around · Sleep quality · Amenities

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

Hospitality · Comfort · Family · Beach · Cleanliness · Decor · Location · Sleep quality · Kitchen · Indoor spaces · Pool · Accuracy · Outdoor spaces · Noise · Value · Nearby · Wifi · Biking

Luxury Home with Pool and Putting Green! Close to

Totally Beachin’ by AMI Locals VPL20-000155, DWE5105909 Welcome to Totally Beachin’, a luxury beach home just seconds from the Anna Maria Sound and a short walk to Bradenton Beach’s sparkling beaches! This three-bedroom, three-bath home offers a private resort-style pool, an inviting in ground putting green, and plenty of outdoor seating for relaxing or entertaining. Located in a peaceful neighborhood near the historic Bridge Street shopping and dining district, this getaway combines

Pool · Walkability · Beach · Hospitality · Location · Hot tub · Decor · Access · Quiet · Nearby · Family · Cleanliness · View · Accuracy · Kitchen · Heating · Indoor spaces · Biking · Amenities

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.

Location · Hospitality · Beach · View · Walkability · Kitchen · Nearby · Cleanliness · Quiet · Comfort · Family · Condition · Amenities · Decor · Outdoor spaces · Bathroom · Wifi · Indoor spaces · Getting around · Pool · Sleep quality · Checkout · Value · Check-in

60ft. Water Slide - Golf Simulator - Mini Golf

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.

Family · Pool · Hospitality · Cleanliness · Beach · Nearby · Walkability · Accuracy · Indoor spaces · Hot tub · Layout · Back garden · Location · Kitchen · Condition · Amenities · Decor · Bathroom · Comfort · Access · Sleep quality · Checkout · Value · Biking · Check-in

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

Beach · Hospitality · Location · Family · Cleanliness · Pool · View · Getting around · Walkability · Amenities · Hot tub · Nearby · Indoor spaces · Decor · Kitchen · TV · Outdoor spaces · Comfort · Bathroom · Condition · Sleep quality · Biking · Accuracy · Pets · Quiet · Parking · Back garden · Air conditioning · Check-in · Layout · Wifi · Laundry · Access · Checkout · Value

The Shady Mermaid by Duncan Real Estate

Welcome to The Shady Mermaid! A luxury ground-level vacation home just a 3-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen has ample counter space, gas cook top and oven, extra-large fridge/freezer and wine cooler making meal prep a breeze.

Back garden · Beach · Decor · Pool · Walkability · Location · Kitchen · Nearby · Indoor spaces · Cleanliness · Amenities · Condition · Accuracy · Hospitality · Outdoor spaces · Hot tub · Bathroom · Quiet · Family

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!

Hospitality · Cleanliness · Pool · Family · Beach · Hot tub · Kitchen · Location · Accuracy · Layout · Comfort · Grill · Check-in · Decor · Outdoor spaces · Nearby · Bathroom · Quiet · Getting around · Condition · Sleep quality · Amenities · TV · Indoor spaces · Walkability · Long stay · Back garden · Access · Checkout · Shared spaces · Air conditioning

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 🌊✨.

Hospitality · Location · Beach · Walkability · Pool · Cleanliness · Nearby · Family · Indoor spaces · Outdoor spaces · Comfort · Condition · Hot tub · Decor · TV · Bathroom · Amenities · Pets · Kitchen · Grill · Layout · Quiet · Parking · Getting around · Back garden · Sleep quality · Checkout · Air conditioning