World-Class Siesta Key Vacation Rentals & Tropical Hotel
Condo
Jamaica Royale T64
BRIGHT, AIRY PENTHOUSE. SLEEPS 6...As you awaken in the morning, open the curtains over your "wall of glass" in your large master bedroom equipped with king-size bed, FIOS television, new Caribbean-styled furnishings, en suite bath with shower, secured Wi-Fi internet access throughout and unlimited domestic calling land-line telephone. Gaze at the waves breaking on the Gulf of Mexico, the fine white quartz sands of Crescent Beach, beach-walkers and soaring gulls. Perhaps you will choose to step out onto your very large Lanai with phenomenal views, of sea, sky and tropical foliage. This lanai is accessible from both the master bedroom and the living areas, through large walls of sliding glass. Your private well-equipped lanai includes several chairs and lounging chaises. Open and airy, it is also carefully designed to let you enjoy your vacation in privacy from neighboring units. After enjoying a cup of coffee or the morning paper, you may prepare your breakfast in the generous, airy and fully equipped kitchen. While in the kitchen, you will enjoy the view of the pool and grounds below or the Gulf of Mexico, from your kitchen window. Perhaps you will choose to do a load of laundry in the conveniently located Bosch Axxis full-size washer/drawer in the kitchen area. If you choose to sunbathe on the beach or at the pool, both are conveniently located just steps away from the elevator serving your unit. Perhaps after a day at the beach or poolside, you and your friends or family will enjoy lounging in the generous well equipped living room/dining room/kitchen combination. Prepare your dinner in the suite or at the convenient outside grilling area immediately off the beach. Dine outside on the beach, on the grounds, at your dining room table that seats 6 or perhaps on your private lanai looking at the stars above-the choice is yours! If instead you choose to venture out, Siesta Key Village with great dining and shopping options is a short drive, walk (either along the beach or sidewalks) or an enjoyable pedal-cab ride away. Along the way, you will pass the newly expanded public beach with full-menu snack bar, large parking lot, tennis courts, showers, bathrooms, seasonal special events and popular Sunday evening drum circle performances most weeks. Or, you may choose to go "off the Key" via one of two bridges to parts beyond including many great dining and shopping options such as St. Armand's Circle, Downtown Sarasota with its Saturday Farmer's Markets and many other events. Or, explore the quieter side of Siesta Key at Turtle Beach. All is yours to explore. When you return, you will be free of parking hassles given your reserved parking spot just steps away from the elevator serving the unit. The second bathroom serving the entire unit also includes a tub/shower combination for your guests or children. With only four units per floor and no guests above you, you will enjoy the sound of the seashore, instead of fellow guests, as you drift off to sleep. Tomorrow is another day with many memorable options to enjoy that will keep you coming back for years to come to this special beachfront penthouse unit. This unit has a 7 night minimum Saturday to Saturday rental policy, but can be booked for less to fill gaps. We will do our best to accommodate any request.
Studio
Jamaica Royale 014
Renovated Interior and Updated Look Coming by May 2025 Recently updated with a brand new kitchen, guests will enjoy all-new Samsung Stainless Steel Appliances, new soft close/dovetail white shaker cabinets, new Quartz counters, and a new sink/faucet. With the large pantry cabinet for extra storage, there is plenty of room for all your needs. With an enhanced, fresh Coastal Theme, this unit was recently updated with a new white Queen Murphy Bed system with drawers/shelves and a new Comfort Tech Elite Aurora 12-inch Mattress, New Luxury Vinyl Flooring Throughout, Fresh Paint, New Baseboards, New Curtains, comfortable new Sleeper Sofa, bistro set, and a New Water Heater! The bathroom has a walk-in shower with bench seating. This condo also features a full-size patio with tables, four chairs, and an umbrella. This condo unit is located in the garden/pool area of our beautifully landscaped property, with a short walk to the beach (one of the closest studios in the complex). Check the site map of our website for a better perspective of where this condo is located. Take a stroll along Siesta Key's #1 beach, then come back and enjoy any of the three heated pools on the grounds, or entertain with a BBQ at the community patio, which also has a shuffleboard, or entertain at the BBQ beachside and watch a beautiful sunset. This unit has a 7-night minimum Saturday to Saturday rental policy but can be booked for less to fill gaps. We will do our best to accommodate any request.
House
Sunset Gulf
Sunset Gulf by Siesta Key Luxury Rental Properties 551 Beach Rd Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Your dream beach vacation awaits at Sunset Gulf! This four-story luxury home boasts eight bedrooms and five-and-a-half baths and is just three houses away from the nearest beach access. Highlights • 2-minute walk to the beach • Beach views • Private pool with in-ground spa • Balconies • Ping Pong table • Indoor bar • Poolside bar and TV • BBQ grill • Outdoor seating This backyard is the perfect place for both fun and relaxation! It features a pool with an in-ground spa and ample lounge chairs for each guest to soak up the sunshine. The covered patio provides an outdoor dining table, a BBQ grill, a seating area, and a bar equipped with a sink, fridge, television, and bar stools. Additionally, the game room can be accessed through the sliding glass door. On the second floor, you will find the primary living space of the house. It includes a spacious kitchen with stainless steel appliances, ample cookware, a bar with seating, and a dining table. The area is furnished with a large sectional sofa, a loveseat, and a TV for guests to enjoy their favorite shows. To reach the third floor, you can take the elevator and find a great seating area along with a complete bar that has a wine fridge. Here, friends and family can practice their mixology skills and enjoy their drinks while taking in the incredible Gulf views from the deck. There are two stunning primary bedrooms, complete with walk-in closets, private balconies, and ensuite bathrooms with double vanities, walk-in showers, and soaking tubs to pamper yourself. There are four more king bedrooms and two bunk bedrooms - two of which have ensuite bathrooms. Furthermore, there is a hall bathroom with a convenient walk-in shower, a half bath, and laundry rooms on both floors. Room Details -Primary Bedroom, 4th floor: King bed, balcony, and ensuite bathroom with walk-in shower and tub plus a rollaway twin bed -Second Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with walk-in shower and tub -Third Bedroom, 4th floor: King bed and ensuite bathroom with walk-in shower and tub -Fourth Bedroom, 3rd floor: King bed and ensuite bathroom with double vanity and walk-in shower - Fifth Bedroom, 3rd floor: King bed -Sixth Bedroom, 3rd floor: King bed and queen futon -Seventh Bedroom, 3rd floor: Twin over Full Bunk Bed with Twin Trundle -Eighth Bedroom, 4th floor: Twin over Twin Bunk Bed and Twin with Twin Trundle From an indoor game room with a ping pong table and gulf views from just about every room to a sparkling pool, you and your guests will love the amenities this home has to offer! We are confident that you will enjoy your stay at Sunset Gulf! - Elevator available to all floors except fourth floor. This property has an active Ring doorbell and additional video surveillance on the pool equipment only. This property participates in our Professional Linen Program. This ensures high quality linens and towels are always included for your stay. These are professionally laundered at a commercial facility for every guest. This property does not allow pets. 6 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Townhouse
Our House at the Beach C-111
First floor townhouse, few steps inside and outside, no elevator. Experience coastal living at Our House at the Beach C-111, a beautifully furnished two-bedroom, two-bath condo just steps from the stunning Siesta Key Beach, Florida. This rental perfectly blends comfort and convenience, with a 4-minute walk to the beach and a 2-minute stroll to the Siesta Key trolley stop. Enjoy easy access to the sparkling Gulf waters, vibrant dining options, and charming boutiques in Siesta Key Village, making it an ideal getaway for families and friends. Highlights • 4-minute walk to the beach • 2-minute walk to trolley stop • Balcony • Water views • Washer and dryer • TV in each bedroom • 1 parking spot • Community pool • Two Tennis Courts • Community BBQ grills Our House at the Beach is located directly across the street from Siesta Key Beach, home to mesmerizing white sands and unforgettable Florida sunsets. This complex is set around a scenic lake, and features a private community pool, a covered pavilion area with a BBQ, a picnic area, and two tennis courts for guests to enjoy. Our House at the Beach C-111 features a generous bi-level layout with separate dining and living room spaces, making it perfect for family gatherings or entertaining friends. The eat-in kitchen is fully stocked with pots, pans, dishware, and flatware, and it includes full-sized appliances such as a dishwasher, microwave, and washer and dryer for your convenience. Step out from the bright, spacious living room to your private balcony, where you can breathe in the fresh air while overlooking beautifully landscaped grounds. The primary bedroom suite offers its own balcony, an ensuite bathroom, and a large closet with a dressing area, creating a personal retreat for relaxation. The second bedroom provides comfortable accommodations with an adjacent full bathroom, ideal for guests or family members. Book your stay at Our House at the Beach C-111 today, where relaxation and adventure meet on the beautiful shores of Siesta Key, Florida! Experience unforgettable sunsets and create lifelong memories in this beach paradise.
Condo
Jamaica Royale 204
Jamaica Royale 204 by Tropical Sands Accommodations 5830 Midnight Pass Rd, Unit 204, Siesta Key, Florida Welcome to Jamaica Royale 204: Your Family-Friendly Beachfront Getaway! This updated 2-bedroom, 2-bathroom condo located on the second floor of Tower II is the perfect choice for a memorable family beach vacation. Just a short elevator ride away, you’ll find one of America’s best beaches, where you can enjoy the quartz white sands and explore nearby attractions. Families will love the complimentary FIOS TV and secure private Wi-Fi, making it easy to unwind and stay connected after a day of sun and fun. Highlights • Private Beach Access • Balcony with Dining Table • Beach Views • In-unit Washer and Dryer • 3 Shared Heated Pools • Community Shuffleboard Court • Two Shared BBQ Areas • 1 Assigned Parking Spot Jamaica Royale is a gated beachfront complex offering private access to the stunning white sands of Siesta Key Beach. Enjoy three heated community pools, shuffleboard courts, two laundry rooms, shared gas grills, and outdoor showers for the perfect vacation in Sarasota, Florida. The inviting interior of Jamaica Royale 204 features a cozy living area that creates a warm ambiance for relaxation. The updated kitchen is fully equipped for all your meal prep needs, with a dining area designed for family meals and gatherings. Enjoy al fresco dining on your private balcony while taking in the tropical breeze and beautiful beach views. Jamaica Royale 204 includes a spacious primary bedroom with a king bed and an ensuite bathroom that features a convenient walk-in shower. The second bedroom is perfect for kids, furnished with two full-size beds. The hall bathroom includes a shower-tub combo, providing ample space for everyone to prepare for beach adventures. Don’t miss your chance to create unforgettable family memories at Jamaica Royale 204! Book your stay today and immerse yourself in the beauty and fun of Siesta Key’s stunning beaches!
Condo
Gulf and Bay Club- B701
Have your dreams come true in this amazing penthouse condo that has an open floor plan with panoramic views from almost every room in the home. As you walk through the condo, enjoy spectacular views of The Gulf of Mexico, Gulf and Bay Club’s lush landscaped courtyard, pools, pond, fountains and even views of downtown Sarasota. After enjoying a day on one of the most beautiful beaches in the world, kickback, relax and continue to enjoy the same beautiful views from the comfort of your air-conditioned condo. This condo is one of the few in Gulf and Bay Club with three bedrooms and three full baths. As it is the end unit, its location is away from foot, elevator and car traffic, allowing you to hear the peaceful sounds of seagulls and waves. The spacious master bedroom has a king size bed, extra-large walk-in closet with full size washer and dryer, lockable jewelry drawer, not mention a terrific view of Siesta Key beach. The ensuite master bathroom has stone and tile throughout with double sinks, vanity area, walk in shower with grab bars and built in seat. The second bedroom has two full size beds, ensuite bathroom with tub/shower combo, separate vanity sink area, walk in closet and its own beautiful views of Siesta Key beach. The cozy third bedroom has a full-size bed with the third bathroom just down the hall. The kitchen has an abundance of European cabinetry with granite countertops and high-end appliances. There is an instantaneous hot water tap for a cup tea or a Keurig for your morning coffee. If wine is your fancy, enjoy the wide assortment of stemware that waits in its own built-in glass cabinetry. The lucky chef of the night will have everything they need in this well stocked kitchen and will never feel left out of the party with the wide-open floor plan. Whether it’s just you or you're entertaining guests, there is plenty of seating with views to go around. These unbelievable views and spacious open floor plan are just waiting for your arrival! We hope you love B701 as much as we do!
House
Siesta Palooza
Siesta Palooza by Siesta Key Luxury Rental Properties 332 Avenida De Mayo Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Resort island living awaits at Siesta Palooza! This eight-bedroom and eight-bath home is a true masterpiece with a picture-perfect backyard with a sparkling pool, large spa, and covered patio with high-end seating, dining table, grill, and a game room with a TV and ping pong table! Highlights • Less than a 10-minute walk to the beach • Private pool and in-ground spa • Rooftop deck • Ping Pong table Guests can unwind and enjoy their stay, whether lounging in the coastal indoor seating area with a large TV, sitting on the rooftop deck and soaking up the sun, or indulging their culinary passions in the fully-equipped kitchen with high-end appliances and essential amenities. With seating for up to six people, the kitchen island seamlessly connects to the main dining area and deck, featuring modern dining room tables. Siesta Palooza boasts five king rooms, including the primary suite, a queen room, and two bunk rooms, all of which are beautifully decorated to exude beach vibes. Each room is furnished with dressers and televisions, and has either an ensuite bathroom or easy access to a hall bath. Additionally, we have provided a washer and dryer for your convenience. On the fourth floor, you'll find an excellent hang-out spot with video games and a large sofa that can be easily converted into a sleeper sofa. There's also a sleeper sofa in the main living room. Room Details -Primary Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with a shower and tub combination -Second Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with double vanity and walk-in shower -Third Bedroom, 3rd floor: King bed, balcony, and jack-n-jill bathroom with shower and tub combo -Fourth Bedroom, 3rd floor: Queen bed and jack-n-jill bathroom with shower and tub -Fifth Bedroom, 4th floor: King bed, balcony, and ensuite bathroom with a shower and tub combination -Sixth Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with a shower and tub combination -Seventh Bedroom, 3rd floor: Full over Full bunk bed with Twin trundle and ensuite bathroom with walk-in shower -Eighth Bedroom, 2nd floor: Twin over Full bunk bed with Twin trundle -Bonus, 4th floor: Queen sleeper sofa -Bonus, 2nd floor: Queen sleeper sofa The location is unbeatable, just a few steps away from the grocery store, restaurants, shops, and vibrant nightlife. Plus, with the nearby Siesta Key Beach access points just a short walk or bike ride away, you'll be able to take in the stunning surroundings with ease. Book now and start planning your remarkable getaway! - This property has active video surveillance on the exterior public approach areas and the pool equipment. This property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. 5 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Condo
Midnight Cove II 944C
Welcome to Midnight Cove II and thanks for checking us out! We think we are quite spectacular if we must say so ourselves! Siesta Key and our local community are brimming with shopping, dining, art and culture. BEACH INFORMATION: Our deeded beach access is located across the street from the crosswalk. Guests should direct themselves to beach access 12 which is approximately 350 yards to the south (left) after crossing the bridge. We provide1 roll of toilet paper, 1 bar of soap in each bathroom, and 1 trash bag per trash can, but not replenished. Ride the Siesta Key Breeze Trolley it's FREE and find relief knowing you won't be driving around the village searching for a parking spot. Take a stroll to the beach via our dedicated beach access and enjoy a little sand-in-your-toes experience. Our Bayside property provides views of the Intracoastal waterway while also being within walking distance to the Gulf of Mexico. Our property offers a heated swimming pool with a large pool deck complete with lounge chairs and seating with sun shade, 2 tennis courts with 1 of them having pickle ball lines, basketball court, club house, barbecue grilling area, a beautiful observation deck at the end of our property and even private docks available to rent for your boat. During season (February and March) we have popular events that include live music, Yoga classes and much more. We are located just minutes from beautiful downtown Sarasota, the world renowned Ringling Museum of Art, as well driving distance to such attractions as Walt Disney World and Busch Gardens Tampa Bay. Sarasota is a top vacation destination in Florida and Midnight Cove II offers the perfect location and setting to enjoy it. We truly are the perfect location for your getaway. World acclaimed Siesta Beach is made famous by its sugar-fine, quartz-white sand, not to mention the thriving Siesta Village. Visit us and you will see why Siesta Key should be on your bucket list. Siesta Key beach has been ranked the best beach in America. Ready to pack up that bathing suit and a pair of flip flops? If you're looking for a condominium rental, look no further! Our sprawling tropical oasis can accommodate a minimum 7 night rental to, well, forever if you like! So, welcome aboard and let us help you begin your accommodation planning! Maybe you want to stay forever and have found your happy place? Check out our website for a listing of units for purchase. We have an agent on site that can assist you in the purchase of one of our fabulous Vacation Condominiums. This 4th floor, 1400 sq. ft. unit is accessible by both an elevator and stairs and can accommodate up to 4 people. The washer and dryer are conveniently located in the laundry room. This unit also has a 26 ft. screened in lanai with strikingly beautiful views of the lagoon, grounds canals and docks.
Condo
Jamaica Royale 705
Jamaica Royale 705 by Tropical Sands Accommodations 5830 Midnight Pass Rd, Unit 705, Siesta Key, Florida Discover the ultimate family beach getaway at Jamaica Royale 705, your ideal Siesta Key condo! This spacious two-bedroom, two-bath vacation rental is just steps from the pristine sands of Siesta Beach, providing easy access for sunbathing, swimming, and exciting beach volleyball. Families will love the close proximity to charming shops and family-friendly restaurants in Siesta Village, just a quick trolley ride away on the Siesta Key Breeze, allowing for effortless exploration and unforgettable memories. Highlights • Private Beach Access • Balcony with Beach Views • Outdoor Dining Table • 3 Shared Heated Pools • Community Shuffleboard Court • Two Shared BBQ Areas • 1 Assigned Parking Spot Jamaica Royale is a gated beachfront complex offering private access to the stunning white sands of Siesta Key Beach. Enjoy three heated community pools, shuffleboard courts, two laundry rooms, shared gas grills, and outdoor showers for the perfect vacation in Siesta Key, Florida. The spacious indoor lounge area is designed for family comfort, featuring cozy seating and a TV for movie nights. Step out to the large lanai and balcony that offer breathtaking views of Siesta Key’s stunning beaches. The well-equipped kitchen makes preparing family favorite meals easy, and the dining table comfortably seats six, creating a welcoming space for sharing meals and memories together. The primary bedroom is well-appointed for parents, featuring a king bed, Gulf views, a TV, and an ensuite bathroom with a walk-in shower. Designed with kids in mind, the second bedroom has two full beds, a TV, and convenient access to the hall bathroom with a shower-tub combo. Book your stay at Jamaica Royale 705 for the perfect family beach vacation in Siesta Key, Florida, and make memories that will last a lifetime!
Condo
Jamaica Royale 028
#28 features a courtyard brick patio with two chaise lounges and table and chairs to enjoy all day sun while the opposite side brick patio provides all day shade. Amenities include a recent remodeled bath with walk in shower plus a half bath and washer and dryer. Nicely decorated with mostly new furniture in the living room and bedroom and an ample sized kitchen for the chef with new appliances. Close to one of three pools and a pleasant stroll to the beach. This unit has a 7 night minimum Saturday to Saturday rental policy, but can be booked for less to fill gaps. We will do our best to accommodate any request. MAXIMUM OF 2 PEOPLE IN JUNE, JULY, AND AUGUST. Renovated Interior and Updated Look Coming by May 2025
Condo
Our House at the Beach E-301
Renovated Unit directly across from Siesta Beach with views for miles! Smell the salt in the air and feel the sand in your toes! Our House at the Beach 1055 Beach Road Unit E-301 Sarasota, Florida Welcome to our third floor, two bedroom, two bath unit with two 24-foot balconies. This western exposure front corner unit overlooks the Gulf of Mexico from nearly every room and showcases famous sunsets over the #1 Beach in the world. A secure and modern elevator lobby will take you to your home away from home where once inside, luxury vinyl tiles flow through every room in the unit. The modern kitchen features new cabinetry with gorgeous counter tops and new stainless steel appliances. The dining room and spacious main living have floor to ceiling, entire wall-length sliding glass doors framing the west and north views. Both open-air balconies are covered and tiled, looking out over Beach Rd. and Siesta Key Beach. The layout offers privacy in the primary suite with two closets, including a walk-in closet and a bathroom that boasts chevron tiled floors, an elongated floating vanity, double sinks, plus a custom shower with an accented tile and dual shower heads. Guests also enjoy provided linens and towels, a private laundry closet, a pull out queen couch in the living room, and assigned, covered parking. Additional upgrades include a new tankless water heater and a new electrical panel. This Our House at the Beach Tower unit is directly across from the #1 rated Siesta Beach, with easy access to its public beach, pavilions, playgrounds, and picnic areas and has immediate access to the community heated pool and tennis courts. We are located approximately 1 mile from the vibrant yet quaint Siesta Village (walking, biking OR shuttle service can be enjoyed), where shopping, dining, nightlife and all manner of fun rental experiences await.
House
Island Sun
Island Sun by Siesta Key Luxury Rental Properties 559 Beach Rd B Siesta Key, Florida Welcome to Island Sun, a gorgeous beach getaway with three-bedrooms and two-bathrooms located directly across from Siesta Key Beach! Enjoy the Florida sunshine in the shared backyard that has a sparkling pool. Vacation dreams come true at Island Sun! Highlights • 2-minute walk to the beach • Shared Pool • Dog Friendly • Close to shops and restaurants Take the stairs up to your private side of the duplex and immediately feel the vacation vibes as you walk in. There is a beautiful nautical seating area with two sofas and a large TV. The kitchen has a stove, a fridge, basic cookware, and there is a chic dining table as well as countertop seating. Through the sliding glass doors is the deck that has seating and overlooks the pool. The primary bedroom has bright beach décor, a premium mattress, plenty of storage space, and a TV. The guest bedrooms have calming colors with a delightful nautical touch. The upstairs bathroom has a walk-in shower and the downstairs bathroom has a shower and tub combination. A washer and dryer are available for guest use. Room Details -Primary Bedroom: King bed and TV -Second Bedroom: King bed and TV -Third Bedroom: Full over Full bunk bed with Twin Trundle and TV Are you traveling with friends and family? Island Sun’s neighboring duplex is available for rent and has three bedrooms and three and a half baths, totaling six bedrooms and five-and-a-half bathrooms. Search for Siesta Sun on our Browse Rentals search page. - This property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. This property has an active Ring doorbell and additional video surveillance on the pool equipment only.
