Luxury rentals in Siesta Beach

Siesta Beachfront Paradise: Infinity Pool & Spa!

Siesta Beachfront Paradise by Siesta Key Luxury Rental Properties Home in Sarasota Florida, 34242 Indulge in the ultimate beachfront luxury at Siesta Beachfront Paradise, a stunning new construction home that offers an unparalleled escape on the renowned Siesta Key. With 8 spacious bedrooms and 8 ensuite bathrooms, this exquisite property is perfect for large families or groups. Situated just steps from the world-famous Siesta Key Beach and 3-minute stroll to the charming Siesta Key Village.

5 out of 5 average rating, 10 reviews

Home in Siesta Key

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.

5 out of 5 average rating, 4 reviews

Home in Anna Maria

Luxury home! Pool and Spa, Golf cart, and Bikes

Sweet Caroline by AMI Locals Home in Anna Maria, FL VR23-000009 Welcome to Sweet Caroline, a newly constructed four-bedroom and four-and-a-half bathroom home just one small block from the quartz-sanded Gulf of Mexico Beaches. This modern beach house is outfitted with every luxury amenity you can think of, from a rooftop deck that boasts sensational views, an elevator to take you from each floor to an impressive backyard with a private pool, in-ground spa, a putting green, and a fabulous,

Home in Anna Maria

Lap of Luxury by Duncan Real Estate

Welcome to Lap of Luxury! This home is new as of 2022 and has been meticulously built and designed to create a space for full relaxation. Lap of Luxury is only 150 steps from the white sand beaches of the Gulf of Mexico with beautiful views from every floor. It features 4 bedrooms and 5 and a half baths and is just a short stroll away from the historic shopping area along Pine Ave and the famous Bean Point beach area. Step through the zen inspired courtyard area to the main entrance.

Home in Holmes Beach

Tiki By The Sea by Duncan Real Estate

Welcome to Tiki by the Sea! This beautiful, centrally located 5-bedroom, 3-bathroom pool home has 1,921 under A/C square feet of elevated living space and offers the best of Island vacationing. Up to ten guests will be accommodated very comfortably inside and out. From the quality quilts and linens on the beds, TVs in 4 of the 5 bedrooms and several fantastic outdoor areas nothing has been spared to provide a perfect beach getaway. HIGHLIGHTS 1921 sq. ft. Pool side Tiki bar

Home in Holmes Beach

Seaside Haven by Duncan Real Estate

Seaside Haven is an elegant Island property that promises an unforgettable experience. The 4 bedroom and 3 1/2 bath pool home is located on the Avenues in Holmes Beach and just a short flipflop walk to the Gulf powdery white beaches. This house features tasteful coastal-themed dcor that prioritizes guest comfort. Its gourmet kitchen and open floor plan provide ample space for family gatherings, complemented by a functional and relaxing outdoor living area by the pool with a firepit.

5 out of 5 average rating, 5 reviews

Gulf Views/Walk to St. Armands & Beach-Resort Pool

Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience! Per City of Sarasota's Rental Ordinance - This home must be rented for a minimum of 7 nights, and it has a max occupancy of 12 adults, *but children under 6 years of age do not count toward the City's max occupancy count. Vunique Vacations restricts the total occupancy of the home to 16 persons, including adults and children under 6 years of age.

Home in Holmes Beach

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.

Home in Bradenton Beach

Elevator, Endless Summer by SeaBreeze Vacation

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER 4/27/23! All Drivers must be over the age of 21. Driver’s must provide valid US Driver’s License and US Vehicle Insurance. Endless Summer is the latest addition to SeaBreeze Vacation's portfolio. Pristine, newly constructed home features 7 beds/6 baths, an elevator, fantastic pool & spa, an EV Charger, and is just a 4-minute stroll from the shoreline

5 out of 5 average rating, 4 reviews

2440 Arlington Park Luxury House

Welcome to 2440 Floyd Street, a stunning, modern retreat in the heart of Sarasota. This spacious 6-bedroom, 4.5-bathroom home offers luxury, comfort, and privacy, making it the perfect getaway for families, groups, and corporate travelers. With a heated pool, private rooftop terrace, and a detached guest house, this home offers a true resort-style experience just minutes from Siesta Key Beach, Lido Key, and downtown Sarasota.

2430 Arlington Park Luxury House

Welcome to 2430 Floyd Street, a stunning modern retreat in Sarasota’s historic Arlington Park neighborhood. This 6-bedroom, 4.5-bath home offers 2,743 sq. ft. of stylish living space, perfect for families, groups, or business travelers seeking a luxurious and relaxing getaway. With a heated pool, outdoor kitchen, rooftop terrace, and detached guest house, this home delivers the ultimate Sarasota experience.