Condo
Harbor Towers- 417
Highlights • Bay Views • Two Community Pools • Three Community Tennis Courts • Fitness Center • 2-week minimum stay required Harbor Towers 417 by Tropical Sands Accommodations 5855 Midnight Pass Rd, Unit 417 Siesta Key, Florida Harbor Towers Yacht and Racquet Club is an incredible bayfront condominium located directly on the Gulf Coast Intracoastal Waterway. This complex features two heated pools, three tennis courts, a fitness center, a grilling patio, and a Marina (Additional fee, registration, and documentation required). Harbor Towers 417 is an updated two-bedroom and two-bathroom condo on the fourth floor boasting beautiful Bay views and is just across the street from the powdery white sands of Siesta Key Beach. Enjoy the fully equipped kitchen, chic living room, and screened-in lanai with a full dining set that overlooks the bay's calm waters. Sleep soundly in the primary bedroom, which has lovely beach décor and a modern ensuite bathroom with a walk-in shower. The second bedroom is wonderfully decorated with plush bedding and has an ensuite bathroom with a shower and tub combination that guests can also access through the living area. A sleeper sofa in the living room and a washer and dryer are available. Room Details -Primary Bedroom: King bed and ensuite bathroom with a walk-in shower -Second Bedroom: Queen bed -Living Room: Sleeper Sofa Hop on the free Siesta Key Breeze Trolley right in front of the complex and explore the entire island, including the Siesta Key Beach Pavilion, Siesta Key Village, and Turtle Beach.
Condo
Bay Oaks E-14
Bay Oaks E-14 by Tropical Sands Accommodations 6157 Midnight Pass Rd #E 14 Sarasota, Florida Welcome to your perfect family getaway at Bay Oaks Condominium, a delightful two-bedroom, two-bath vacation rental located on beautiful Siesta Key, Florida. Nestled among tropical foliage and serene pathways, this condo offers a relaxing atmosphere just minutes away from the world-renowned Siesta Beach. Enjoy strolls under coconut palms and oak trees while taking advantage of nearby attractions, including restaurants and shopping. Highlights • 10-minute Walk to the Beach • Community Fishing Pier • Private Washer and Dryer • Private Balcony • Heated Community Pool • 1 Covered Parking Space • Tennis and Pickleball Court • Easy Access to Siesta Key Breeze Trolley Stop At Bay Oaks, family fun awaits! Enjoy sunny days at the heated pool, challenge each other on the tennis courts, and share delicious meals at the BBQ area. Don’t forget to catch stunning sunsets from our private fishing pier—perfect for creating cherished memories and enjoying quality time together! Step inside Bay Oaks E-14 and discover a beautifully designed open floor plan that exudes a light and inviting beachy charm. The cozy seating area is perfect for family movie nights with a Smart TV that makes streaming favorites a breeze. The fully equipped kitchen features a variety of appliances and all the cookware necessary for delicious family meals. Enjoy casual breakfasts at the kitchen island, gather for more formal dinners at the dining table, or unwind on the balcony with a glass of wine as the island breeze gently surrounds you after the kids are fast asleep. Each bedroom at Bay Oaks E-14 is designed for comfort and entertainment, featuring smart and direct TVs for endless viewing options. The primary suite offers a plush king-size bed, a spacious walk-in closet, and an ensuite bath with a walk-in shower. Perfect for kids or guests, the second bedroom includes twin beds and its own private bath, complete with a newly tiled bathtub shower combo. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower -Second Bedroom: Two Twin beds Ready for Your Next Family Adventure? Pack your swimsuit and toothbrush, and get ready for a memorable family vacation at Bay Oaks Condominiums on Siesta Key! - This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. This property does not allow pets of any kind. 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 see our Tropical Sands Accommodations Rental Policies for full details. 1 car 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 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
704N Crescent Arms
Beautiful 7th Floor Penthouse Condo with Gulf Front View * 2 bedroom, 2 bath * Shared Resort amenities, private beach access, heated pool, bbq area, beach chairs provided * Fully updated unit * Private screened-in lanai with Gulf view * Located on Siesta Key Enjoy every moment of your vacation to sunny Florida in style at this stylishly renovated unit overlooking the Gulf of Mexico! The bright and welcoming living and dining area offers water views and comfortable seating to relax, while the new kitchen features all-new appliances for your convenience. It’s a great combination for casual home-cooked dinners at sunset without even leaving the comfort of your own “home away from home”. Able to accommodate up to 6 guests, the new primary bedroom features an ensuite bathroom, and the second bedroom has 2 Queen beds. All are decorated in a chic coastal style with new furnishings. Unit layout: Primary bedroom - King bed with ensuite bathroom with walk-in shower Bedroom 2 - 2 Queen beds Second hallway bathroom with walk-in shower Resort amenities are available for guest use, including private beach access, beach chairs, a bbq area and a heated pool, plus covered parking. Located in South Village on Siesta Key, this condo is perfectly situated close to restaurants, shopping and happy hour hotspots. Inquire today! *1 week minimum stay required
Condo
Siesta Beach House #312
If you're looking for a great vacation location on beautiful Siesta Key, then look no further. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorgeous white sandy beaches, or swim in the crystal clear waters of the Gulf of Mexico. Come join us for the perfect vacation.
Duplex
Off The Hook - A
Highlights • Less than a 5-minute walk to the beach • Less than a 5-minute walk to Siesta Key Village • Private patio • Pet friendly Off The Hook A 328 Calle Miramar A Siesta Key, Florida Welcome to Off The Hook - A, a fun and sunny vacation rental located just a few minutes' walk to world-renowned Siesta Key Beach! With two bedrooms and one bath, a full kitchen, and private patio space, this cheerful unit is perfect for a couple or family with young kids. Arrive and open the door to a comfortable living area that invites guests to sit back and chill out together and decide where to head out and explore first. This home’s location is ideally situated within easy walking distance of both the beach and Siesta Key village, where you will discover local beach shops, ice cream places, and especially delicious seafood restaurants. Or you can stay in and cook at home, in the fully equipped kitchen with dining area for sharing meals and quality family time. Relax and unwind in the primary bedroom, where you will drift off to sleep and dream of the gentle Gulf of Mexico waves. The second bedroom is ideal for kids, with two twin beds. Both bedrooms share the hallway bathroom with granite countertops and a shower and tub combination. Room Details -Primary Bedroom: King bed -Second Bedroom: Two twin beds -Shared Hallway Bathroom with shower and tub combination Step outside on the private patio with a bistro table perfect for coffee in the morning or dining al fresco in the warm tropical breezes. There is also a shared outdoor space featuring a BBQ grill and comfortable lounge chairs for basking in the Florida sunshine. Additionally, there is a shared duplex laundry room for guest use. Book your next Siesta Key vacation to Off The Hook – A now, and get ready to enjoy a trip to paradise! *Please note: 1 car maximum can 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. This property allows pets - there will be an additional non-refundable pet fee charged upon approval. Pet Policy: Dogs only are allowed under certain conditions, and all animals, including service animals, must be disclosed and approved prior to arrival. We cannot accept cats. Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds are allowed. Please see our Tropical Sands Accommodations Policies for full details. 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 a refund. This property participates in our Professional Linen Program. This ensures that high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest.
Condo
Peppertree Penthouse #803
Highlights • Private beach access • 2 community pools • Community gym • Tennis and Pickleball court • Private lanai Peppertree Penthouse #803 by Tropical Sands Accommodations 1125 W Peppertree Dr #803 Siesta Key, FL 34242 Welcome to Peppertree Penthouse #803! This two bedroom and two bath condo boasts a tropical vibe and amazing views of the Gulf of Mexico and Siesta Key beach. The Peppertree property as a whole is the epitome of old-school Florida. You'll enjoy access to a private beach with chairs, a grill area, two sparkling pools, a fitness center with a sauna, a fishing pier, and tennis and pickleball courts. As soon as you step inside, prepare to be dazzled by the living space! Features a brand new large 85-inch TV. The fully equipped kitchen has stainless steel appliances, essential cookware, a gorgeous granite breakfast bar that comfortably seats three, and a cozy dining table that accommodates four. The kitchen effortlessly blends into the seating area, where you'll settle down to watch your favorite shows on a large-screen TV. Indulge yourself in a peaceful slumber in the tranquil haven of the primary bedroom. The room is adorned with upscale coastal-inspired furnishings, a brand-new large TV, and offers stunning views of the Gulf. It also features a beautiful ensuite bathroom with a double vanity, ample cabinet space for your essentials, and a shower and bathtub combination. The second bedroom has plush bedding and a workspace, perfect for students or remote workers. It also has an updated ensuite bathroom with a walk-in shower. To make your stay more convenient, this unit includes a washer and dryer and a sleeper sofa. Room Details -Primary Bedroom: King bed and ensuite bathroom with a double vanity and shower and tub combo -Second Bedroom: Two twin beds and ensuite bathroom with walk-in shower -Lanai: Queen Sleeper Sofa You're in for a treat with the large enclosed lanai! It offers breathtaking views of the nearby beach and can be accessed from the primary bedroom and living area. You'll love the cozy sofa, lovely dining table, and comfy wicker armchairs, making this space perfect for relaxation and entertainment. We can't wait to have you as our guest. Book today! - No pets are allowed in this home. This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. 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 see our Tropical Sands Accommodations Rental Policies for full details. 1 designated parking pass can be obtained at the office and there is plenty of guest parking. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. 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
Gulf Holiday Unit 11
This beautifully renovated, well-appointed one bedroom condo is perfect for a romantic getaway!! Gulf Holiday is just a short walk to Siesta Key Beach voted #1 beach in the U.S and the Siesta Key Village shops, restaurants, and nightlife. This 2nd floor unit has a newly renovated kitchen with custom cabinets, new appliances, including dishwasher. Bedroom is Newly furnished with a King sized bed with pillow top mattress. New furnishings in living room with a Flat screen TV as well as in the bedroom. Perfect location and size for a beach vacation.
House
Off Tropic
Off Tropic by Tropical Sands Accommodations 1746 Hillview St Sarasota, FL 34239 VR24-00055 Welcome to Off Tropic, a stunning vacation home with three bedrooms and three luxurious bathrooms. This home features a lovely screened-in pool area, perfect for relaxing. Located near the breathtaking Siesta and Lido Key beaches providing easy access to the Gulf, while the nearby sophisticated Downtown Sarasota and iconic St. Armands Circle boast world-class dining, shopping, and entertainment. Highlights • Private pool with in-ground spa • Less than 5-miles to the beach • Outdoor living space • Washer and dryer • Near restaurants and shops As soon as you walk-in, you’re met with gorgeous views of the tropical backyard. You’ll love the warm, homey vibe of the living room with a seating area and large tv and it seamlessly opens to the home’s dining room. The modern kitchen boasts granite counters, stainless steel appliances, built-in oven, range and microwave, a walk-in pantry and a family style breakfast bar. Plus, there is dedicated office space for remote workers and students. Prepare to be transported to an opulent retreat. The primary bedroom has luxe furnishings, a comfortable bed, and a great walk-in closet. The ensuite bathroom has stunning touches throughout, including a double vanity, a walk-in shower, and a soaking tub. The second and third bedrooms are appointed with soft linens and storage space, and the third bedroom has an ensuite bathroom. There is a hall bath and a laundry room to provide convenience. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower and tub -Second Bedroom: Queen bed -Third Bedroom: Two Twin beds and ensuite bathroom with shower and tub combo Off Tropic's screened-in lanai epitomizes outdoor luxury, perfect for entertaining and embracing the Florida lifestyle. Lounge by the gorgeous pool and spa, enjoy the bar and BBQ grill, and gather around the outdoor dining table. Every moment is a celebration of relaxation and indulgence in this tropical paradise! - No pets are allowed in this home. These premises are monitored by video surveillance in select exterior areas. This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. 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 see our Tropical Sands Accommodations Rental Policies for full details. 3 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 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
Living the Dream Villa
Living the Dream Villa by Tropical Sands Accommodations 6005 Midnight Pass Rd #S-10 Sarasota, FL 34242 Welcome to Living the Dream Villa, a charming two-bedroom condo just a 5-minute stroll from the stunning Siesta Key beaches. Perfect for families and friends, this inviting retreat offers relaxation and fun. Explore vibrant Siesta Key Village nearby, filled with boutique shops, delicious restaurants, and exciting nightlife, along with outdoor adventures like kayaking and paddleboarding. Your dream getaway awaits! Highlights • Beach Access within 5-minute walk • Private Washer and Dryer • Work desk • Private Outdoor Space • Community Shuffleboard • Community Pool • Community Dock • Outdoor Seating and Grill • 5-minute walk to Siesta Key Breeze Trolley As a guest at Living the Dream Villa, you’ll have access to the amenities of two associations! Enjoy shuffleboard and a scenic dock in Provincial Gardens, ideal for fishing and watching boats pass by. Just across the street, Aloha Kai offers a refreshing community pool and direct beach access, ensuring you have everything you need for an unforgettable getaway! Your private outdoor space includes an outdoor dining table and a plush outdoor seating area for enjoying the Gulf breeze. Inside your new favorite home away from home is an open-concept layout featuring a fully equipped kitchen and a dining table set for six, exuding a warm, rustic, nautical vibe. Adjacent is a spacious living area with plush seating and a TV, perfect for relaxation and entertainment. This villa features two bedrooms: one with a luxurious King bed and desk perfect for remote workers, the other with two comfy Full-size beds. Enjoy an ensuite with a walk-in shower and dual vanities, plus a shared bathroom with a shower-tub combo and single vanity. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower -Second Bedroom: Two Full Size Beds Experience the perfect blend of relaxation and adventure at Living the Dream Villa, where every moment is an opportunity to unwind and explore. Book your stay today! - This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. This property does not allow pets of any kind. 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 see our Tropical Sands Accommodations Rental Policies for full details. 1 car 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 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
Siesta Beach House #207
If you're looking for a great vacation location on beautiful Siesta Key, then look no further. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorgeous white sandy beaches, or swim in the crystal clear waters of the Gulf of Mexico. Located on a private lane that leads right to the beach . . . no through traffic and no streets to cross – just a short stroll to the famed white sands of Crescent Beach. 1 WEEK MINIMUM RENTAL REQUIRED
House
Casa Mango
Highlights • Shared Dock • Screened-in Private Pool • 2-mile drive from Siesta Key Beach • Ping Pong Table • Kayak Casa Mango by Tropical Sands Accommodations 7123 Roland Oaks Circle Sarasota, FL 34231 Welcome to Casa Mango! This vibrant three-bedroom, two-bath vacation home has a stunning pool and a shared dock just down the street where your friends and family can enjoy kayaking and paddleboarding on Sarasota Bay. The world-famous Siesta Key sunsets and white powdery sand beaches are just a short drive away. Pack your bags and get ready to soak up the Florida sunshine! Instantly feel the vacation vibe as you watch the palm trees gently sway as you pull into your private driveway. Once you open the door, you will be welcomed into an inviting seating room that boasts spectacular pool and lanai views, creating a seamless indoor-outdoor living experience. The kitchen has stainless steel appliances, cooking basics including pots and pans, and opens to the kitchen table. This Old Florida-style home offers a split-bedroom layout perfect for multiple groups or families. traveling together. The primary bedroom is a beautiful light blue to provide a calming ambiance and features a bright ensuite bathroom with double vanity, walk-in shower, and a standalone tub. The second bedroom is appointed with a King bed and a closet to store vacation essentials. The third bedroom has a Full over Queen bunk bed, making it ideal for kids or a small family. There is a hallway bathroom with a shower and tub combination. To ensure every guest has a comfortable stay, there is a bonus room with a twin trundle daybed. A washer and dryer are available for guest use. Room Details -Primary Bedroom: King bed and ensuite bathroom with walk-in shower and standalone tub -Second Bedroom: King bed -Third Bedroom: Full over Queen bunk -Bonus: Twin daybed with trundle Step into the private oasis where the possibilities for relaxation are endless. Take a dip in the pool, refresh with a drink in one of the chairs by the pool, swing in the hammock, or play yard games with friends, family, and even your pets! A three-person kayak, with paddles in the shed and paddle boards in the garage, is excellent for exploring the deeded water access and shared dock. - This home requires a 30-night minimum stay. This property only allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Tropical Sands Accommodations Rental Policies for full details. 3 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. This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. 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 see our Tropical Sands Accommodations Rental Policies for full details.
Condo
Stay On Tropic #4
Stay On Tropic #4 by Tropical Sands Accommodations 1739 Siesta Drive #4 Sarasota, FL 34239 Relaxation and sun-soaked days await you at Stay On Tropic #4, a modern second-level condo designed for your comfort and enjoyment. Ideally located for beach enthusiasts and adventurers alike, you'll be just a short drive away from the mesmerizing white sands of Siesta Key Beach, as well as the vibrant shops and restaurants of downtown Sarasota. Highlights • 1.7 miles to the Beach • Screened-In Patio • Shared Backyard • Near Shopping and Dining • Dog friendly with approval and additional fee This inviting retreat features a delightful shared outdoor space with ample comfortable seating and multiple BBQ grills, perfect for casual gatherings and cookouts under the sun. As you step into the living space, you’ll find a plush sofa and a TV for cozy evenings in, along with a fully equipped kitchen featuring a cooktop and essential cooking supplies for preparing delicious meals. The chic dining table comfortably seats four, making it perfect for family dinners or game nights. An adorable screened-in lanai offers additional seating, allowing you to unwind while soaking in the tropical surroundings and refreshing breezes. The primary bedroom is a restful haven featuring a sumptuous King bed, nightstands with ambient lighting, and ample space to store your beach bags and essentials. Refresh yourself in the stylishly updated hall bath, complete with a walk-in shower for your convenience. For added flexibility, the living room also includes a Queen sleeper sofa, providing extra accommodation options for your group. Room Details -Primary Bedroom: King bed -Living Room: Queen sleeper sofa If you're traveling with friends or family, Stay On Tropic offers three additional condos on the property for rent. These charming accommodations range from one to two bedrooms and can be booked separately as Stay On Tropic #1-#4, or combined as a larger Tropical Stay through our "Go to unit" search option. Don’t miss your chance to create unforgettable memories in this tropical paradise! Book your stay at Stay On Tropic #4 today and experience the perfect blend of relaxation and adventure. - This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. This property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Tropical Sands Accommodations Rental Policies for full details. 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 see our Tropical Sands Accommodations Rental Policies for full details. 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.
