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199 properties available
Peppertree Penthouse #803 by Tropical Sands Accommodations Welcome to Peppertree Penthouse #803, a spacious 2-bedroom, 2-bath Siesta Key condo with breathtaking Gulf views, private beach access, and a spacious enclosed lanai perfect for sunset dining. Located within the highly desirable Peppertree community on Siesta Key Beach, this home provides u
Peppertree Penthouse #803
Condo
2
bedrooms
2
baths
6
guests
5
(1)
Harbor Towers 121 by Tropical Sands AccommodationsWelcome to Harbor Towers 121, a beautifully updated two-bedroom, two-bath Siesta Key vacation rental located in the gated Harbor Towers Yacht and Racquet Club on Midnight Pass Road. Designed for extended stays with a 13-night minimum, this stylish residence features a sleek modern kitchen, two king
Harbor Towers 121
Condo
2
bedrooms
2
baths
6
guests
4.8
(5)
A wonderful 3 bedroom, 2 bath corner unit with a direct view overlooking the Gulf of Mexico and America’s #1 rated Siesta Beach. If you’re looking for a beach retreat where you can watch the beautiful sunsets over the Gulf from your lanai and fall asleep to the sound of waves hitting the white sandy beach, you’ll find it here! If you’re loo
Gulf and Bay Club- F406
Condo
3
bedrooms
2
baths
6
guests
Harbor Towers 530 by Tropical Sands AccommodationsWelcome to Harbor Towers 530, an elevated two-bedroom, two-bath Siesta Key vacation rental located in the gated Harbor Towers Yacht and Racquet Club on Midnight Pass Road. Perched on an upper floor with sweeping waterfront views of the Intracoastal Waterway, tropical palms, and sparkling pool below,
Harbor Towers 530
Condo
2
bedrooms
2
baths
4
guests
Midnight Cove II – Unit 931 - I found paradise!1100 Cove II Place 931 Siesta Key FL 34242Welcome to Midnight Cove II 931C! Nestled in the picturesque Crescent Beach on Siesta Key, our vibrant community is alive with shopping, dining, art, and culture. Enjoy the convenience of the free Siesta Key Breeze Trolley, ensuring smooth exploration without t
Midnight Cove II 931C
Condo
2
bedrooms
2
baths
4
guests
This unit has had a full remodel and is just wonderful. The view out through the courtyard and to the Gulf is breathtaking. And by having an end unit, you also get to enjoy extra natural light and views out of your kitchen and living room windows to the side. The lanai is comfortably set up with table/chairs for dining and a gliding loveseat for en
Gulf and Bay Club- C201
Condo
2
bedrooms
2
baths
4
guests
5
(1)
Harbor Towers Unit 319 by Tropical Sands AccommodationsHarbor Towers Unit 319 is a spacious three-bedroom, two-bath condo located within the gated waterfront Harbor Towers community on Midnight Pass Road in Siesta Key. Designed for families or small groups, this inviting retreat offers a comfortable layout, bright coastal interiors, and a screened
Harbor Towers 319
Condo
3
bedrooms
2
baths
6
guests
Midnight Cove II – Unit 620- Just Sunning Around1400 Cove II Place 620 Siesta Key FL 34242This lovely 3-bedroom, 2.5 bath with washer and dryer condo boasts Tommy Bahama-style furnishings and stunning views overlooking the swimming pool and lush landscaping. The primary bedroom features a king bed, the guest bedroom includes a twin bed, and another
Midnight Cove II 620D
Condo
3
bedrooms
2
baths
1
Half baths
6
guests
5
(1)
Midnight Cove II – Unit 333 - Bayside Beauty1700 Cove II Place 333, Siesta Key FL 34242Welcome to Midnight Cove II Unit 333F! Experience a luxurious getaway in this exquisite updated 3rd-floor condominium, featuring premium finishes and stunning views from the spacious balcony. Perfect for families or friends, this inviting 2-bedroom, 1-bath with a
Midnight Cove II 333F
Condo
2
bedrooms
1
baths
1
Half baths
6
guests
Midnight Cove II – Unit 224 Beautifully Appointed Vacation Rental!1800 Cove II Place 224, Siesta Key FL 34242Experience the charm of Midnight Cove II with this inviting 2-bedroom, 1.5 bathroom condo nestled near the beautiful shores of Crescent Beach on Siesta Key. This delightful bayside property features a walkway to Crescent Beach Public Access
Midnight Cove II 224F
Condo
2
bedrooms
1
baths
1
Half baths
6
guests
Harbor Towers 628 by Tropical Sands AccommodationsWelcome to Harbor Towers 628, a beautifully appointed three-bedroom, three-bathroom Siesta Key vacation rental located on Midnight Pass Road. Perfect for extended stay guests with a 13-night minimum, this spacious condo offers comfortable coastal living just minutes from world famous Siesta Key Beac
Harbor Towers 628
Condo
3
bedrooms
3
baths
6
guests
5
(1)
Midnight Cove II – Unit 932 - Let's Relax 1100 Cove II Place 932 Siesta Key FL 34242Welcome to Our Spectacular 932 View at Midnight Cove II! This updated 2-bedroom, 2-bathroom condo is not only modern and stylish but also ideally located in the building closest to the beach. Savour breathtaking views of our beautifully landscaped 14-acre grounds w
Midnight Cove II 932C
Condo
2
bedrooms
2
baths
4
guests
5
(2)
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