Luxury rentals in Siesta Beach

Showstopper Beach Home Pool Spa Waterfall Elevator

Welcome to the Kingdom on Hyde, the crowning jewel of Arlington Park homes & a vacation lover's dream. Featuring 4 bedrooms & 6 baths spread over nearly 4000 sq ft w/ 20ft soaring ceilings. This jewel box features a heated pool & spa with dramatic 8ft waterfall feature, Thermador Appliances, commercial grade elevator, custom imported tile & finishes & 2-story living amongst the Live Oaks. Perfectly situated a stone's throw from Arlington Park & a short drive to Siesta Beach & Downtown Sarasota!

Hospitality · Decor · Pool · Beach · Accuracy · Outdoor spaces · Location · Kitchen · Quiet · Comfort · Nearby · Indoor spaces · Cleanliness

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 · Family · Location · Pool · Beach · Outdoor spaces · Indoor spaces · Walkability · View · Hot tub · Kitchen · Nearby · Cleanliness · Getting around · Condition · Barbecue · Value · Comfort

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

Pool · Family · Decor · Getting around · Accuracy · Indoor spaces · Cleanliness · Location · Sleep quality

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

Pool · Hospitality · 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

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.

Hospitality · Location · Beach · Family · Cleanliness · Nearby · Walkability · Indoor spaces · Amenities · Pool · Comfort · Accuracy · Decor · Bathroom · Kitchen · View · Hot tub · Sleep quality · Outdoor spaces · Barbecue · Parking · Getting around · Backyard · Condition · Noise · Value · Air conditioning

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

Island home with Pool and swim-up bar!

The Blue Crab by Anna Maria Vacations Home in Holmes Beach, Florida VRC-000057 Welcome to The Blue Crab, a stunning island retreat just three blocks from Holmes Beach! This luxurious four-bedroom, four and a half bath home boasts a tropically landscaped backyard featuring a private pool with a swim-up bar, fire pit, and hot tub. Surrounded by elegant, coastal farmhouse decor, the open layout offers plenty of space for family gatherings or friends’ getaways. Perfect for those seeking

Family · Location · Pool · Getting around · Comfort · Walkability · Accuracy · Beach · Hospitality · Hot tub · Kitchen · Biking · Cleanliness · 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 · Wi-Fi · Indoor spaces · Getting around · Pool · Sleep quality · Checkout · Value · Check-in

Infinity Pool - 2 waterslides - Rooftop Gulf View

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.

Hospitality · Family · Walkability · Pool · Indoor spaces · TV · Beach · Accuracy · Hot tub · Noise · Kitchen · Checkout · Nearby · Laundry · Check-in · Cleanliness

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 · Location · Hospitality · Family · Cleanliness · Pool · View · Getting around · Walkability · Amenities · Nearby · Hot tub · Indoor spaces · Decor · Kitchen · TV · Outdoor spaces · Bathroom · Comfort · Condition · Biking · Accuracy · Pets · Sleep quality · Quiet · Parking · Air conditioning · Check-in · Layout · Wi-Fi · Laundry · Backyard · 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.

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