Luxury rentals in Siesta Key

Find and book unique accommodation on Airbnb

Top-rated luxury holiday rentals in Siesta Key

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Luxe

Home in Anna Maria

5 out of 5 average rating, 5 reviews

Island home with Pool and swim-up bar! Best

The Blue Crab by AMI Locals Holmes Beach Vacation Rental VRC-000057 Welcome to The Blue Crab, a stunning island retreat just two 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 relaxation, recreation,

Luxe

Home in Siesta Key

5 out of 5 average rating, 11 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.

Luxe

Home in Holmes Beach

5 out of 5 average rating, 3 reviews

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

Luxe

Home in Holmes Beach

5 out of 5 average rating, 3 reviews

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.

Luxe

Home in Anna Maria

5 out of 5 average rating, 4 reviews

Private Pool and Game Room! - Boundless Waves

Boundless Waves by Anna Maria Island Accommodations Anna Maria, Florida Welcome to Boundless Waves, an incredible vacation home with six bedrooms and six-and-a-half bathrooms, where friends, family, and pets can relax and have endless fun. You'll be blown away by the resort-style pool and spa, perfect for hours of fun in the sun. Plus, there is a rooftop deck with breathtaking views and a game room, which is a total blast with a ping pong and an air hockey table.

Luxe

Home in Lido Key

5 out of 5 average rating, 6 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.

Luxe

Home in Holmes Beach

5 out of 5 average rating, 4 reviews

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.

Luxe

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

Luxe

Home in Sarasota

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.

Luxe

Home in Lido Key

5 out of 5 average rating, 4 reviews

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

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.

Luxe

Home in Siesta Key

5 out of 5 average rating, 5 reviews

1 min to Beach & Pool - Shell-Abrate Good Times

Please note that this home is in close proximity to an ongoing construction project. Please inquire with the host for more information. Shell-Abrate Good Times by Siesta Key Luxury Rental Properties Home in Sarasota FL 34232 Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key!

Luxe

Home in Sarasota

New Contruction Modern Sarasota Oasis

Welcome to Arlington Oak House, a stunning modern retreat in the heart of Sarasota’s charming Arlington Park neighborhood. This spacious five-bedroom, four-and-a-half-bathroom home offers a luxurious getaway with designer interiors, an inviting outdoor living area, and easy access to the city’s top beaches, dining, and entertainment.