Luxury rentals in Holmes Beach

The exterior of a coastal-style home is framed by lush tropical landscaping. Two palm trees and various shrubs surround the property, while the distinct architecture features a tower and a large covered porch. The garage doors have rustic wooden accents, adding charm to the overall design.

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,

5 out of 5 average rating, 12 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.

4.8 out of 5 average rating, 5 reviews

Home in Lido Key

New Home with Pool, Spa, Waterslide - Seascape

Seascape by Lido Key Vacations Sarasota FL 34236 VR24-00004 Welcome to Seascape, a stunning vacation home boasting eight spacious bedrooms and eight-and-a-half luxurious bathrooms. With a gorgeous private pool, spa, and waterslide, you'll be living in paradise! Plus, the rooftop deck offers incredible views, and it's only a block away from Lido Key Beach, where you can catch breathtaking sunsets. This vacation home is perfect for families and large groups seeking a memorable beach

A wide view of the property showcases a private heated lap pool surrounded by lush greenery and palm trees. An outdoor lounge area can be seen nearby, with seating options and tranquil pathways leading through manicured grass.

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.

Superhost

A private lagoon-shaped pool is surrounded by lush greenery and features two sun loungers. The pool area includes tiki umbrellas for shade and a deck with steps leading to the home, characterized by a charming blue exterior and large windows.

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

A rooftop deck offers a spacious dining table surrounded by comfortable chairs, showcasing a view of the sparkling Gulf waters and coastal landscape. The area is enhanced by clear blue skies and distant clouds, providing a serene setting for outdoor meals.

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.

A spacious backyard is featured, showcasing a private pool with a tranquil water feature. Surrounding palm trees add to the tropical ambiance. Comfortable lounge chairs are placed poolside on well-manicured grass, inviting relaxation and enjoyment under the clear blue sky.

Experience luxury! Pool, Rooftop, Near Beach!

The Colony by Anna Maria Island Accommodations Home in Holmes Beach, Florida Welcome to The Colony, a custom-built vacation home with a breathtaking private backyard that features a spacious pool, hot tub, and a covered patio, great for entertaining and making memories with your friends and family! This home has four bedrooms and four and a half baths and is close to the Gulf of Mexico and the white sandy beaches for viewing legendary Anna Maria Island sunsets.

5 out of 5 average rating, 6 reviews

The exterior of a three-story vacation home is highlighted, showcasing large glass doors and multiple balconies. Lush greenery surrounds the property, while a rooftop deck can be seen, providing additional outdoor space. The driveway offers ample parking with two garage spaces visible.

Home in Lido Key

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.

A private heated pool is surrounded by tropical landscaping and wooden decking. A Tiki Hut with bar seating and string lights enhances the space, while a waterfall feature adds tranquility to the area, creating a serene outdoor retreat.

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.

A spacious outdoor area is featured, showcasing a modern pool surrounded by comfortable lounge chairs. Lush greenery and palm trees enhance the setting, while a shaded patio area offers ample seating for dining and relaxation.

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

The modern exterior of the home features a clean white facade with large windows, providing natural light. A welcoming entrance is marked by stylish light fixtures and palm trees, while colorful landscaping enhances the overall curb appeal.

Home in Sarasota

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.

An aerial view of a modern coastal home highlights its spacious rooftop deck with ample seating. Surrounding palm trees and a backdrop of the Gulf of Mexico contribute to a serene coastal setting under a bright blue sky.

Home in Lido Key