Weekly Stays


Properties Available 217 properties available
Gulf Holiday Unit 11 by Tropical Sands Accommodations Welcome to Gulf Holiday Unit 11, a newly renovated 1 bedroom, 1 bath second floor condo ideal for a romantic and friendly Siesta Key getaway. Just a 2-minute walk to Siesta Beach and steps from Siesta Key Village’s restaurants, shops, and nightlife, this charming retreat blends cozy comfort with
Gulf Holiday Unit 11
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating 4.9 (25)
Jamaica Royale – Unit 048 by Tropical Sands AccommodationsWelcome to Jamaica Royale Unit 048, a newly renovated ground-floor villa just steps from the quietest pool in the community. This upscale one-bedroom retreat blends modern upgrades with the relaxed charm of Siesta Key, offering the perfect balance of comfort and convenience. From the private
Jamaica Royale 048
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4 (1)
Siesta Beach House #201 by Tropical Sands Accommodations Welcome to Siesta Beach House #201, a comfortable and family friendly two bedroom, one and a half bathroom condo located on the quiet south end of Siesta Key. Tucked away on a private lane with gated beach access, this inviting retreat places you just a short walk from the powdery white sands
Siesta Beach House #201
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
HalfBathrooms 1 Half baths
Guests 4 guests
Rating 5 (2)
Jamaica Royale T54 by Tropical Sands Accommodations Welcome to Jamaica Royale T54, a beautifully decorated beach condo with 2 bedrooms and 2 bathrooms, perfect for families. Located on stunning Siesta Key Beach, this spacious unit offers breathtaking views of the #1 beach, just steps away. Enjoy nearby attractions like Siesta Key Village, packed wi
Jamaica Royale T54
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Jamaica Royale 082 by Tropical Sands AccommodationsWelcome to Jamaica Royale 082, a recently renovated two-bedroom, two-bath condo offering a comfortable and stylish retreat just steps from the world famous Siesta Key Beach. Located within the beautifully maintained Jamaica Royale community, this inviting villa features modern updates, spacious liv
Jamaica Royale 082
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Jamaica Royale 503 by Tropical Sands Accommodations Welcome to Jamaica Royale – Unit 503, a spacious two-bedroom, two-bathroom beachfront condo overlooking the Gulf of Mexico on beautiful Siesta Key Beach. Perfect for families or couples, this coastal retreat combines comfort and convenience with private beach access, three heated community pools,
Jamaica Royale 503
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Midnight Cove II 912C! Situated in the heart of Crescent Beach on Siesta Key, our community offers a delightful mix of shopping, dining, art, and culture that is sure to entertain you. Enjoy the complimentary Siesta Key Breeze Trolley, which takes the worry out of parking while you explore the picturesque village. Take a pleasant stroll
Midnight Cove II 912C
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
Jamaica Royale 004 by Tropical Sands AccommodationsWelcome to Jamaica Royale 004, a beautifully remodeled one-bedroom, one-bath garden villa located at the beachfront Jamaica Royale resort on Siesta Key. Recently updated with modern finishes, marble and granite accents, and stylish coastal décor, this inviting vacation rental offers a comfortable i
Jamaica Royale 004
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Jamaica Royale 702 by Tropical Sands Accommodations Welcome to Jamaica Royale 702 — a true beach paradise! This 2-bedroom, 2-bathroom condo offers stunning, expansive views of the beach and Gulf of Mexico from a private balcony and comfortable lanai — as well as from almost every room in this well-appointed home-away-from-home. Ideal for families,
Jamaica Royale 702
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
Welcome to Midnight Cove II 731F and we’re thrilled that you’re considering us for your next unforgettable adventure on Siesta Key! This 3rd floor tropical oasis is bursting with charm, nestled in a vibrant community filled with shopping, dining, art, and culture just waiting for you to explore. Hop on the free Siesta Key Breeze Trolley and effortl
Midnight Cove II 731F
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
HalfBathrooms 1 Half baths
Guests 6 guests
Rating 5 (2)
Jamaica Royale 010 by Tropical Sands AccommodationsWelcome to Jamaica Royale 010, a beautifully renovated two-bedroom, two-bath poolfront villa offering true beachside bliss on Siesta Key. This ground floor retreat combines modern coastal design with unbeatable proximity to both the pool and the powdery white sands of Siesta Key Beach. Thoughtfully
Jamaica Royale 010
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
Jamaica Royale T21 by Tropical Sands AccommodationsWelcome to Jamaica Royale T21, a beautiful Gulf front two-bedroom, two-bath vacation condo located in Tower I at the beachfront Jamaica Royale resort on Siesta Key. This front facing tower unit offers panoramic views of the Gulf of Mexico, allowing guests to enjoy breathtaking sunsets and warm coas
Jamaica Royale T21
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)

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