Trips to Downtown

There are a lot of options in Downtown. If you plan on staying in the Downtown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Downtown:

• Last min cancellation starting June 15th. walk to the beach and st Armand circle
• Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
• Charming Private Garden Cottage hide away in the heart of Sarasota
• Island Vibes + Modern Comfort at Lido Beach!
• Charming Beach Bungalow with Private Pool and steps away from the Beach!
• Roomy Cottage: 4bd3 ba; 2,000 sq ft; 100 ft to beach path; priv pool VR22-00058
• Lido Beach Walk! One block to beach!
• HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
• Coastal Gem!
• Adorable two bedroom one bath condo walk to the beach and st Armand’s circle

There are 329 vacation rentals with private pools near Downtown. Top-rated homes that have access to a swimming pool include:

• Endless Summer
• Tropical paradise! Spa, heated pool, 2 miles from Siesta Key beach, very private
• Beachy Cottage close to Siesta | 3 Bed | Huge Pool
• Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks

If you are looking for a family-friendly vacation home in Downtown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Downtown:

• Sunny 4BR Sarasota Retreat With Hot Tub & Rooftop
• Cozy 2Bd+2 Ba beach cottage; screened Florida rm, sleep porch; VR22-00059
• Tiny House Siesta

Currently, the total number of properties listed in 2026 is over 1850 in the Downtown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Downtown.