World-Class Siesta Key Vacation Rentals & Tropical Hotel
Condo
Jamaica Royale 804
Jamaica Royale 804 by Tropical Sands Accommodations 5830 Midnight Pass Rd, Unit 804, Siesta Key, Florida Experience the ultimate in beachfront living at Jamaica Royale 804, a beautifully designed condo that boasts breathtaking views of the Gulf of Mexico. With 2 spacious bedrooms and 2 bathrooms, this inviting retreat is ideal for families, couples, or friends looking to soak up the sun and enjoy the vibrant atmosphere of Siesta Key. Explore nearby attractions, including charming shops and delightful restaurants in Siesta Village, which are just a short trolley ride away on the Siesta Key Breeze. Highlights • Private Beach Access • Balcony with Beach Views • Outdoor Dining Table • 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 Siesta Key, Florida. Step inside and be welcomed into a bright and inviting living area, featuring a cozy sectional queen sleeper sofa and a large HD smart TV—ideal for family movie nights. The chef’s kitchen is truly a culinary delight, equipped with stainless steel appliances, a convenient breakfast bar, and a formal dining table set for six, all enhanced by remarkable views of the beach. From the living space, walk out to the inviting balcony, where you can enjoy alfresco dining while soaking in spectacular views of the Gulf, Point of Rocks, and Sarasota Bay. The outdoor table with seating for four and the chaise lounge provide perfect spaces for both meals and sunbathing. The primary bedroom offers a luxurious king bed with beach views, an ensuite bathroom featuring a walk-in shower and double vanity—creating a serene retreat after a day by the sea. The guest bedroom is also furnished with a king bed and features easy access to the nicely updated hall bathroom with a shower-tub combo, ensuring comfort for all guests. Embrace everything this tropical paradise has to offer, with easy access to Siesta Key Beach, delightful local attractions, and the tranquility of a beachfront condo. Reserve your dream getaway today and make Jamaica Royale 804 your home away from home!
Studio
Jamaica Royale 009
Renovated Interior and Updated Look Coming by May 2025 Modern poolside studio/efficiency unit located on our beautifully landscaped property. This unit is located right next to Pool #2! The appliances and furniture have been updated along with granite countertop. Beautiful leather sleeper sofa and 50" flat screen TV and DVD player. With the Murphy bed and sleeper sofa, two people who rent can have their own bed! Walk to the beach with coffee and enjoy any of the 3 heated pools on the grounds along with our lighted shuffleboard courts. Note: This unit is a 1 to 2 person rental. 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 **Please Note - While this home is guest ready, there are interior doors missing in the foyer that do not impact privacy or safety.** 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 077
Renovated Interior and Updated Look Coming by May 2025 Complete front-to-back renovation with enlarged bathrooms and kitchen. Beautifully appointed 2 bedroom, 2 bath garden villa just steps from the USA's #1 beach. This unit is adjacent to Pool #2 which is a heated, fresh water amenity on our beautifully landscaped property. Kitchen: Gorgeous open concept kitchen with all the small appliances you need. New windows and doors, porcelain floors, granite countertops, and ceiling fans throughout. Master Bedroom: This en suite bedroom features a king size bed, leather recliner, and 22" flat screen TV. The enlarged master bathroom with Roman shower offers a shower seat and grab bar. The granite top sink has a vanity table and makeup mirror. Guest Bedroom: This bedroom contains 2 queen beds, just right for viewing the 26" flat screen TV/DVD. You are welcome to attach your favorite electronic games (gets the kids out of the den). The enlarged guest bathroom has a tub and shower with grab bar. Living Room: Sit on the sofa, loveseat, or rocker-recliners to enjoy the 51" hi-def television with DVD player. Available for your viewing pleasure: HD channels and On Demand movies. The secure, wireless FIOS Internet capability within this unit is available so you do not have to use your data plan. There are also cordless telephones, an answering machine, hair dryers, split garbage/recycle cabinet, beach toys, and beach towels! Kitchen is well stocked with your necessities including a Keurig! Enjoy the enlarged patio with outdoor shower after a day at the beach. Be sure to check out the owner's other units (#75 and #76) next door. All three units have now been renovated to the same comfortable floor plan with all new interiors. 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.
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
Gulf and Bay Club- C310
Welcome to a nicely updated 2 bed/ 2 bath condo located steps from Americas #1 beach, Siesta Key! Come to relax and put your feet in the powder white sand and take a dip in the Gulf of Mexico. Walk on the beach and take in the breathtaking sunsets! Gulf and Bay Club offers many amenities that you can enjoy during your stay. It has 3 heated swimming pools, tennis courts, pickleball courts, shuffleboard, racquetball court, basketball court, fitness center, hot tub, dry saunas, game room and more! Everything you need to enjoy your vacation located all in one place! Welcome to Gulf and Bay Club!
Condo
Gulf and Bay Club- B309
Gulf and Bay Club B309 by Tropical Sands Accommodations 5780 Midnight Pass Rd #B309 Sarasota, Florida Welcome to Gulf and Bay Club B309! This stunning two-bedroom, two-bath condo is the perfect retreat for those seeking a home-away-from-home experience. You'll appreciate the comfortable accommodations, fantastic community amenities, and the close proximity to Siesta Key attractions. Highlights • Gorgeous condo • Washer and dryer in unit • 2-minute walk to the beach • Private Beach Access • 3 Shared heated pools • Shared Tennis, pickleball, Racquetball, basketball, and shuffleboard courts • Shared Fitness Center • Community electric vehicle chargers • 5-minute walk to trolley stop • 1.8 miles to Siesta Key Village Gulf and Bay is a fabulous beachfront condominium complex with private beach access to Siesta Key Beach and its world-famous white sands and warm waters. Perfect for older adults and families, the complex features three heated pools, saunas, a hot tub, and courts for tennis, pickleball, racquetball, and shuffleboard. Enjoy the fitness center and relax at the tiki-themed BBQ areas surrounding the tranquil lakes, creating a serene and enjoyable environment for your stay. Gulf and Bay Club B309 has been beautifully updated, offering a fresh and clean feeling that makes it feel like home from the moment you walk in. The bright, open living space is enhanced by large windows, flooding the room with natural light. The spacious seating area has ample sofa seating and a flat-screen television, and the modern kitchen is fully equipped with pots, pans, utensils, and all the necessary cookware to prepare your family favorites. Adjacent to the kitchen, you'll find a dining table set for four, ready for enjoyable meals. The primary bedroom features a luxurious King bed and an elegant ensuite bathroom, complete with a double vanity, spacious closet, and a walk-in shower. The second bedroom offers two comfortable queen beds, perfect for family or guests. Additionally, a full bath is located in the hallway, along with a washer and dryer for your convenience. Book your stay at Gulf and Bay Club B309 today and begin your new annual getaway tradition in paradise.
Condo
Jamaica Royale T24
Jamaica Royale T24 by Tropical Sands Accommodations 5830 Midnight Pass Rd, Unit T24, Siesta Key, Florida Find your ultimate escape at Jamaica Royale T24! This modern beach condo is just steps from the pristine white sands of Siesta Key Beach, offering everything you need for an unforgettable family getaway on Florida's Gulf Coast. Highlights • Private Beach Access • Private Balcony with Beach Views • FIOS Wi-Fi • 3 Shared Heated Pools • Laundry Facility • Community Shuffleboard Court • Two Shared BBQ Areas • 1 Assigned Parking Spot Located a short stroll from the Siesta Key Breeze Trolley, you're minutes away from the lively Siesta Key Village. Enjoy a diverse selection of dining venues, charming shops, delightful ice cream parlors, inviting coffee shops, and vibrant bars—all within easy reach! 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. Step inside Jamaica Royale T24 to discover a welcoming, tropical living space, featuring a plush sectional sofa and a television that leads to the balcony, where you can enjoy breathtaking Gulf sunsets. The updated kitchen includes stainless steel appliances with island seating for three and a dining table for four. Plus, this unit offers private, secure FIOS Wi-Fi for seamless internet access throughout your stay. The primary bedroom boasts a luxurious king-size bed and an ensuite bathroom with a walk-in shower, providing a peaceful sanctuary after a day in the sun. The guest bedroom features two full beds and easy access to the hall bath with a shower-tub combo. Don’t hesitate—book your stay at Jamaica Royale T24 today and create unforgettable memories on the beautiful Siesta Key Beach!
Condo
Sea Club II Unit 7E
Sea Club II Unit 7E by Tropical Sands Accommodations 5955 Midnight Pass Rd, Unit 7E Siesta Key, FL Welcome to Sea Club II Unit 7E! This two-bedroom and one-bath bayfront condo is perfect for a couple or small family looking for a Siesta Key getaway! Located across from Sarasota on the Intracoastal Waterway, it is just steps away from Siesta Key Beach and a quick trolley ride to Siesta Key Village, offering an array of coastal boutiques, ice cream parlors, coffee shops, and locally raved restaurants. Highlights • Private beach access • 1 parking spot • Community pool • Community fishing pier • Community boat basin (up to 24’) • Community grills and tiki hut • Laundry facility onsite • 4-minute walk to trolley stop As a guest at Sea Club II, you'll have exclusive access to some amazing amenities designed to make your stay unforgettable, including a swimming pool, BBQ grills, and a poolside tiki hut. For water enthusiasts, there’s private beach access just across the street, along with a fishing pier and dock, perfect for your aquatic adventures. Inside this ground-level condo is an intimate coastal retreat featuring a comfortable seating area with a TV, a dining table set for four, and a well-equipped kitchen ready for all your culinary adventures. Both bedrooms offer soft bedding, dressers, and a TV for entertainment. Don’t miss out on this ideal Siesta Key getaway—book Sea Club II Unit 7E today and start your seaside adventure!
