Condo
Casa Siesta 2
Casa Siesta 2 by Tropical Sands Accommodations 6711 Midnight Pass Rd APT 2, Sarasota, Florida Welcome to Casa Siesta 2, the ultimate beach getaway for couples! This one-bedroom, one-bath condo is just minutes from Crescent Beach, charming restaurants, and a local beach market. Plus, with the Siesta Key trolley stop only three minutes away, you and your loved one can easily explore the island’s best attractions together. Highlights • 6-minute walk to the beach • 3-minute walk to trolley stop • Ground-level condo • Screened-in lanai • Beach chairs • Near restaurants • One parking spot Inside, you'll find a cozy seating area with a flat-screen TV, a dining table for four, and a fully equipped kitchen ready for your culinary adventures. The screened-in lanai offers a romantic indoor-outdoor experience with chic seating, creating a serene and intimate atmosphere perfect for unwinding together. The primary bedroom has a king bed, TV, a dresser, and easy access to the hall bath with a shower and tub combination. Embark on a Romantic Beach Getaway! Book with Tropical Sands Accommodations and indulge in a tranquil escape designed for two. Reserve your dream retreat now, and let us help you create unforgettable memories by the sea!
Condo
Harbor Towers- 514
Harbor Towers – 514 by Tropical Sands Accommodations 5855 Midnight Pass Rd, Unit 514 Siesta Key, Florida Escape to paradise at Harbor Towers 514, the perfect couples' getaway! This lovely 5th-floor Siesta Key condo features one bedroom and one bath, offering stunning bay views from the screened-in lanai. Just a short 7-minute walk to the world-renowned Siesta Key Beach, and with the free Siesta Key Breeze Trolley stop conveniently located in front of the complex, you’re perfectly situated to explore the island’s charm, including Siesta Key Village and Turtle Beach. Highlights • 7-minute walk to the beach • 2-minute walk to Siesta Key Breeze Trolley stop • Screened-in lanai • Two heated community pools •Three community tennis courts • Fitness center • Shared BBQ area • Marina • 1 parking spot • 2-week minimum stay 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). Inside Harbor Towers 514, you’ll find a well-equipped kitchen with an array of appliances, a dining table set for four, and a cozy living area with a sofa and TV to unwind after a day of adventure. The screened-in lanai is perfect for savoring your morning coffee or evening cocktails while soaking in the beautiful views. The main bedroom features two queen beds, and the bathroom has a walk-in shower for your comfort. Room Details -Primary Bedroom: Two Queen beds - Living Room: Full Sleeper Sofa Experience the convenience of local attractions, such as beachside restaurants, boutique shopping, and outdoor activities that make Siesta Key a favorite destination. Don’t miss the chance to create lasting memories in this idyllic setting!
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.
House
3360 Higel Avenue
3360 Higel Avenue by Tropical Sands Accommodations 3360 Higel Ave Siesta Key, Florida VR23-00029 Welcome to 3360 Higel Avenue! This gorgeous ground-level home boasts four bedrooms and three bathrooms and is nestled on a serene street, offering the ultimate peaceful escape. The backyard is adorned with lush tropical plants and highlights a glistening pool complete with an in-ground spa. You'll also find an outdoor living area with comfy lounge chairs, a dining table, and a BBQ grill for relaxing and entertaining. Highlights • Less than a 10-minute walk to the beach • 2-minute walk to trolley stop • Private pool with in-ground spa • BBQ grill • Washer and dryer Step inside this beautiful space and be transported to a world of elegance with a charming nautical theme and a variety of seating areas for guests to unwind, watch a movie, or catch up with loved ones. The kitchen has a full suite of stainless steel appliances, an assortment of essentials, and a kitchen island with seating for four. In the formal dining room, you’ll discover a dining table set for six and a bar with a built-in fridge - great for hosting! The primary room boasts beautiful ocean-themed decor with a soothing blue color scheme and features an ensuite bathroom with a double vanity and a convenient walk-in shower. There are two queen guest bedrooms (one with an ensuite bathroom!) and a cozy bunk bedroom available for use. The home also includes a hall bathroom with a shower and tub combo and a complete laundry room with a washer and dryer for your convenience. Room Details -Primary Bedroom: King bed and ensuite bathroom with a walk-in shower -Second Bedroom: Queen bed and ensuite bathroom with a walk-in shower -Third Bedroom: Queen bed -Fourth Bedroom: Two Twin over Twin bunks Hop on a bike, golf cart, or snag a ride on the free trolley to experience the stunning Gulf beaches and charming Siesta Key Village. The village boasts an array of one-of-a-kind boutiques, locally owned restaurants, cozy coffee shops, and delightful ice cream parlors. Your stay at 3360 Higel Ave will be nothing short of awesome! - This property has an active Ring doorbell at the main entrance. 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. 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
1225 Gulf and Bay Bayside
1225 Gulf and Bay Bayside by Tropical Sands Accommodations 1225 Siesta Bayside Dr Siesta Key, FL Welcome to Your Dream Siesta Key Getaway! Experience the perfect blend of relaxation and adventure in this three-level vacation rental featuring three bedrooms and two baths, making it the ideal retreat for friends and family! Highlights • Private Beach Access • 5-minute walk to the beach • Two Heated Community Pools • Community Fitness Center • Community Tennis and Pickleball Court • Community Fishing Dock • Community Picnic area • Walking path Gulf and Bay Club Bayside invites you to enjoy a range of resort-style amenities. Relax with private beach access, take a dip in one of the two heated swimming pools, or stay active in the fitness center. Play tennis or pickleball, fish from the dock, and unwind at the picnic tables. Explore the nature walking path and make the most of your stay in this inviting community. The tropical-inspired main floor living space welcomes you with a cozy seating area, a fully equipped kitchen, and a stylish dining table. Enjoy your favorite drinks at the bar, complete with a drink fridge. Step outside to the screened-in balcony, where you can unwind or enjoy al fresco meals at the additional dining table. This split-level unit features a primary bedroom located downstairs for privacy, while two guest bedrooms are conveniently situated upstairs. Each living level boasts a full bathroom with walk-in showers. Book your stay at 1225 Gulf and Bay Bayside today and create unforgettable memories in beautiful Siesta Key!
Cottage
Crescent Cottage
Highlights • Beach access • Community pool • Private backyard • Washer and dryer • BBQ grill Crescent Cottage by Tropical Sands Accommodations 1144 Seaside Dr Siesta Key, Florida Welcome to Crescent Cottage! This classic one-bedroom and one-bath bungalow is located just 150 yards from the beach, where you’ll feel the warm sand between your toes and the sunshine shining. It’s within walking distance of locally acclaimed restaurants, and a trolley stop is just steps from your front door. Inside is a cozy living space with a kitchen that includes a stove, oven, microwave, toaster, coffee maker, and basic cookware so you can prepare your favorite meals and snacks. There is a chic dining table set for four, and on the lanai, you’ll find a washer and dryer. The primary bedroom has beautiful coastal furnishings, a TV, and a bed covered in plush, crisp linens. The bathroom is modernly updated and boasts a walk-in shower. The sofa in the main sleeping area can be converted into a sleeper sofa to ensure every guest has a rejuvenating night's sleep. Room Details -Primary Bedroom: Queen bed -Living Room: Queen sleeper sofa This delightful beach getaway is made even better by the fact that it features a private backyard! The yard boasts lush greenery, space for dogs to run and play, and an outdoor dining area where you can indulge in delicious meals cooked on the BBQ grill. Don't wait any longer to book your stay at Crescent Cottage and turn your beach vacation dreams into a reality! - 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. 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 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 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
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!
Condo
Stay On Tropic #2
Stay On Tropic #2 by Tropical Sands Accommodations 1739 Siesta Drive #2 Sarasota, FL 34239 Your dream couples getaway awaits at Stay on Tropic #2, a one-bedroom, one-bathroom ground-level condo that warmly welcomes pets! This Sarasota vacation rental is just a short drive from delightful restaurants and unique shops, and it’s conveniently located near Siesta Key Beach, where you can take long walks on the mesmerizing white sands and soak in breathtaking Florida sunsets together. Highlights • 1.7 miles to the Beach • Screened-In Patio • Shared Backyard • Near Shopping and Dining • Dog friendly with approval and additional fee The duplex boasts a delightful shared outdoor space, complete with ample comfortable seating and multiple BBQ grills, perfect for enjoying family cookouts and soaking up the Florida sunshine. Inside is an open living space with a plush sofa, side chair, and TV. The fully equipped kitchen has everything you need from pots, pans, and utensils to prepare family favorites. Enjoy an intimate meal at the high-top table and unwind on the screened-in lanai. The main bedroom has a King bed, nightstands with ambient lighting, and plenty of space to lay out your beach bags. Refresh in the updated hall bath with a walk-in shower. The sofa in the living room can be converted into a sleeper sofa to provide extra accommodation. Room Details -Primary Bedroom: King bed -Living Room: Queen sleeper sofa Book your unforgettable couples getaway at Stay on Tropic #2 today! If you're traveling with friends and family, this location offers three additional condos on the property that are available for rent. These lovely condos vary from one to two bedrooms each and can be rented separately under the name Stay On Tropic #1-#4 or rented as a whole under the name Tropical Stay on our "Go to unit" search option. - 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. 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. 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
Sea Club II Unit 2B
Sea Club II Unit 2B by Tropical Sands Accommodations 5955 Midnight Pass Rd, Unit 2B Siesta Key, FL Welcome to Sea Club II Unit 2B! This one-bedroom, one-bath bayfront condo is a perfect couple's beach escape. Located on the ground level and just steps from Siesta Key Beach, you'll also be a quick trolley ride from Siesta Key Village, where you can explore coastal boutiques, ice cream parlors, coffee shops, and top-rated restaurants. Highlights • Private beach access • Front porch with seating • 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. Upon arriving at Unit 2B, you'll be greeted by a charming front patio with seating—ideal for enjoying your morning coffee or mingling with fellow travelers. Inside, you'll find a cozy seating area with a sofa, side chair, and TV, perfect for relaxing after a day at the beach. The fully equipped kitchen includes all the appliances, dishware, utensils, and cookware you need for preparing quick meals, and a charming kitchen table for two adds a touch of convenience. The main bedroom has a King bed, a TV, a dresser, and a desk. The hall bath has a shower and tub combo. Book your stay at Sea Club II Unit 2B today and enjoy community amenities, beach access, and close proximity to top attractions! We can’t wait to have you as our guest!
Condo
Midnight Cove II - 137
Midnight Cove II – 137 by Tropical Sands Accommodations 6327 Midnight Pass Rd, Bldg. 1, Unit 137 - Siesta Key, Florida Welcome to Midnight Cove II – 137! Discover your perfect getaway in this third-floor condo, offering two bedrooms and one and a half baths—ideal for a family beach vacation! Relish the convenience of private beach access and bring along your boat for some extra adventure. Hop on the nearby trolley for a breezy ride to Siesta Key Village, where vibrant shops, delicious food, lively drinks, and unforgettable entertainment await. Highlights • Private beach access • 4-minute walk to the beach • Community pool • 2-minute walk to trolley stop • Private balcony • Water views • Tennis, pickleball, racquetball, and basketball courts • Fitness Center • Private docks Midnight Cove II is a spectacular bayside condominium complex with private beach access to Siesta Key Beach and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area, fitness room, and a beautiful observation deck and even private docks available to rent. Inside, you'll find a welcoming living space featuring a comfortable seating area with a large TV. The dining table invites shared meals and conversations, all brightened by the bay-facing balcony that offers outdoor seating—ideal for relaxing and watching boats glide by. The kitchen is well-equipped with appliances and cookware to cater to any meal, complemented by sleek granite countertops. The primary bedroom offers a King bed with soft bedding, while the guest bedroom has a full bed with a trundle, perfect for kids. Both rooms are decorated with beach-inspired touches, include TVs, and have ample storage space. The main bathroom offers a walk-in shower, and there's a convenient half bath in the hall. Book your stay at Midnight Cove II – 137 today and create unforgettable family memories!
Condo
Midnight Cove II 134F
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. 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. Step up to this recently updated 3rd floor, 2 bed/1.5 bath Firethorn unit with lots of amenities! The open air balcony overlooks the Intracoastal Waterway where you can look for dolphins and manatees while enjoying the sun. 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. Step up to this recently updated 3rd floor, 2 bed/1.5 bath Firethorn unit with lots of amenities! The open air balcony overlooks the Intracoastal Waterway where you can look for dolphins and manatees while enjoying the sun.
Condo
Stay On Tropic #3
Stay On Tropic #3 by Tropical Sands Accommodations 1739 Siesta Drive #3 Sarasota, FL 34239 Welcome to Stay On Tropic #3, a bright and beautifully designed two-bedroom, one-bathroom condo that’s perfect for a romantic couples retreat or a small family getaway. Ideally situated in Sarasota, this charming rental offers easy access to a variety of delightful restaurants and shops, all while being just a short drive away from the world-renowned Siesta Key Beach, known for its stunning white sands and vibrant sunsets. Highlights • 1.7 miles to the Beach • Screened-In Patio • Shared Backyard • Near Shopping and Dining • Dog friendly with approval and additional fee The duplex features a lovely shared outdoor space that invites you to relax and unwind. With plenty of comfortable seating and multiple BBQ grills, it’s the perfect spot for enjoying al fresco meals, soaking up the sun, or gathering with family and friends for fun-filled evenings under the stars. As you ascend the stairs to your second-floor retreat, you’ll immediately feel refreshed. The spacious living area features a modern seating arrangement with a cozy sofa and TV, seamlessly opening into a private screened-in lanai adorned with plush seating, perfect for catching up with friends or simply enjoying the tranquil surroundings. The kitchen includes a cooktop and essential cookware, complemented by a chic dining table set for four guests. Stay On Tropic #3 is appointed with two Queen bedrooms with luxurious bedding and premium mattresses and has a hall bathroom with an updated walk-in shower. -Primary Bedroom: Queen bed -Second Bedroom: Queen bed For those traveling with friends or family, this location also offers three additional condos on the property for rent. These lovely accommodations vary from one to two bedrooms and can be rented separately as Stay On Tropic #1-#4, or collectively under the name Tropical Stay through our "Go to unit" search option. Book your escape to Stay On Tropic #3 today and create unforgettable memories in sunny Sarasota! - 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.
