World-Class Siesta Key Vacation Rentals & Tropical Hotel
Condo
Jamaica Royale 801
Jamaica Royale 801 by Tropical Sands Accommodations 5830 Midnight Pass Rd, Unit 801, Siesta Key, Florida Enjoy the perfect beach vacation at Jamaica Royale 801, a stunning beachfront condo that offers a romantic getaway for couples. Nestled on the top floor, this beautiful condo features two bedrooms and two baths, showcasing panoramic views of the beach and the Gulf of Mexico—just a quick elevator ride away! Couples will appreciate the condo's close proximity to charming shops and delightful local restaurants in Siesta Village, easily accessible via the Siesta Key Breeze trolley, allowing for effortless exploration and creating unforgettable memories together. 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 Upon entering, you'll be welcomed into an open living space adorned with modern furnishings, including a cozy seating area and a dining table set for six, all complemented by gorgeous beach views. The well-equipped kitchen has everything you need to prepare your favorite meals, and a washer and dryer are included for your convenience. Each bedroom at Jamaica Royale 801 features a king bed, coastal furnishings, a TV, and ample storage space. The first bedroom provides access to the balcony and an ensuite bathroom with a walk-in shower, while the hall bathroom also includes a walk-in shower, ensuring comfort and privacy during your stay. Book your romantic escape at Jamaica Royale 801 for a perfect couples' beach getaway in Siesta Key, Florida, and make beautiful memories that you will cherish forever!
Condo
Jamaica Royale 007
Recently remodeled, with convenient access to pool #2 with it only 15 feet from your patio. The renovation includes: New decor throughout, 65" smart Tv in the living room, all new kitchen including cabinets solid surface counters, GE Monogram appliances, new dinette with 48" glass top, new utility room with ample guest storage and a stack W/D for guest use. other updates are new furnishings such as a King size Sterns and Foster mattress and a very accessible bath that had curb-less entry into a 36' by 60" non-slip pebble floor shower with an oversized glass door and ample grab bars. such a great remodel has revised bathroom layout that has a larger vanity with additional storage and an oversized mirror. Check out the awesome patio with dining table, chairs and an umbrella for fantastic outdoor living. this unit is completely new from top to bottom, come and enjoy this refreshing Zen like vacation oasis! 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-108
Lake house offers a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances, including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the grounds. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Lake House offers central A/C, ample closets and storage space, high-speed Internet, cable TV in the living room and each bedroom, and garage parking for one car. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts. This Lake House unit is right across the street from Siesta Key public beach, making a splash in the ocean or just a walk on the sugar sand beach a just a few steps away.
Condo
Jamaica Royale 075
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 1 out of 3 heated pools 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 (#76 and #77) 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- E505
A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2 clubhouses, and if you like, Americas #1 beach is waiting just outside your door with some of the most spectacular sunsets on the planet. Welcome to Gulf and Bay Club!
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 943C
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.
Condo
Gulf and Bay Club- E203
Come enjoy this 2 bedroom, 2 bath fully renovated unit offering beautiful views, a bright interior, updated décor, and brand-new mattresses. The unit sleeps 6 with a king bed in the master, queen bed in the second bedroom, and sleeper sofa in the living room. Gulf and Bay Club offers resort-style living on America’s #1 beach, which is just steps away. Take advantage of the property’s state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, and 2 clubhouses. Come and experience the most spectacular sunsets and amazing white sand of Siesta Key!
Condo
Fire-Sky Penthouse
Fire-Sky Penthouse by Siesta Key Luxury Rental Properties 9008 Midnight Pass Rd #5 Sarasota, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Escape to paradise at Fire-Sky Penthouse, a three-bedroom, three-and-a-half-bath canal front vacation rental boasting two private outdoor areas. Enjoy meals on the balcony with an outdoor dining table or soak in breathtaking views from the rooftop terrace, perfect for sunbathing or enjoying the sunset. Highlights • Canal front • Rooftop terrace • 6-minute walk to the beach • Piano • Stunning water views • Outdoor dining area • Washer and dryer • 5-minute walk to restaurants • 30-night minimum stay The elevator escorts you directly from a private 2-car garage to your private residence. Inside, the home features an elegant piano and a large sectional sofa, perfect for guests to watch their loved ones perform. The well-equipped chef's kitchen features stainless steel appliances, a cooktop with a hood on the island, and a wine fridge. The kitchen offers plenty of bar and countertop seating, perfect for casual meals or entertaining guests. It seamlessly opens to the formal dining area with a dramatic oval ceiling and to the second living space with comfy seating and dramatic water views. Waking up has never been more delightful than in our primary bedroom, where you'll be greeted by stunning beach and bay views. This luxurious retreat includes a convenient desk area, ample dresser and closet space, and an incredible ensuite bathroom featuring an expansive double vanity, walk-in shower, and a relaxing soaking tub. The two guest bedrooms provide an equally luxurious vibe, with walk-in closets and ensuite bathrooms boasting shower and tub combinations. One of the queen bedrooms also features a private balcony, perfect for morning coffee or evening stargazing. Stay comfortable with our washer and dryer, ensuring all the conveniences of home during your stay. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower and soaking tub -Second Bedroom: Queen bed and ensuite bathroom with shower and tub combo -Third Bedroom: Queen bed and ensuite bathroom with shower and tub combo Whether you’re seeking adventure or tranquility, this rental offers the best of both worlds. Turtle Beach is just a quick walk away, providing breathtaking access to the Gulf of Mexico. To the left and right of Fire-Sky Penthouse, you'll find acclaimed local restaurants, perfect for dining out. Don’t miss out on this perfect getaway—book your stay today and experience the ultimate in coastal living! - This property does not allow pets of any kind. 2 compact cars maximum are able to park at this home. Guest parking is available on a first-come, first-served basis. 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
Jamaica Royale T22
Jamaica Royale T22 by Tropical Sands Accommodations 5830 Midnight Pass Rd, Unit T22, Siesta Key, Florida Enjoy spectacular sunset views and refreshing Gulf breezes from the comfort of Jamaica Royale T22, a charming two-bedroom, two-bath beach condo perfect for a couple's retreat or a small family getaway. Just steps away from the sandy shores and a short walk to the Siesta Key Breeze Trolley, you'll have easy access to the vibrant Siesta Key Village, filled with delightful restaurants, shops, ice cream parlors, coffee shops, and bars! Highlights • Private Beach Access • 3 Shared Heated Pools • Private Balcony • Beach Views • Community Shuffleboard Court • Onsite laundry facilities • 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. This inviting Siesta Key condo features a comfortable living area with a TV, ideal for unwinding after a fun-filled day at the beach. The fully equipped kitchen allows you to whip up your favorite meals, which you can enjoy indoors or on the balcony while taking in beautiful beach views. Both bedrooms are designed for your comfort, offering cozy beds, additional TVs, and ample storage for your belongings, ensuring a restful night's sleep. The primary bedroom includes an ensuite bathroom with a convenient shower-tub, while the hall bathroom features a spacious walk-in shower. Don't miss this opportunity to experience the best of Siesta Key—book your stay at Jamaica Royale T22 today and start creating unforgettable memories by the beach!
Condo
Siesta Beach House #319
Welcome to this cozy beach town home located less than 2 minutes walking distance from beautiful Siesta Beach. All new tile and wood floors and granite counter tops and 3 full bathrooms. Washer and Dryer in unit for your convenience. All new furniture, Master Bedroom has a king bed, and a leather pull-out sleeper chair, the guest bedroom has a new queen and a twin bed. Living room has all new furniture with queen sleeper sofa. Modern well-equipped kitchen, 3 flat screen TV’s, cable and WIFI. Outside patio with table, umbrella and chairs. Siesta Beach House Pool on premises. Beach chairs and loungers are provided! MINIMUM STAY REQUIREMENTS: 1-week minimum Saturday to Saturday reservation required unless booking less than 30 days in advance 3 night minimum may be accepted.
