Siesta Key Rentals: Find Your Perfect Vacation Getaway

Discover your perfect getaway in paradise! Whether you're planning a family vacation, a romantic escape, or a weekend retreat, Siesta Key offers a wide variety of rental options to suit your needs. From luxurious beachfront villas with breathtaking views to cozy cottages nestled in tropical surroundings, Siesta Key rentals provide the comfort and convenience you deserve. Explore our guide to find the best accommodations, tips for booking, and everything you need to make your stay unforgettable. Your dream Siesta Key experience starts here!

Find the Perfect Vacation Rental on Siesta Key

Whether you’re looking for a beachfront condo, a luxury villa, or a family-friendly rental near the village, you’ll find plenty of options on this island paradise. Our Siesta Key vacation rentals directory highlights trusted local management companies, full-service booking providers, and top rental portals to make your search easier.

Use this directory to explore vacation rentals across Siesta Key — from Crescent Beach to Turtle Beach — and discover the best places to stay while enjoying the island’s world famous white sand and sunsets.

Siesta Key Rental Listings

Siesta Key Rentals Map

Vacation Rental Management Companies

These local experts manage dozens of properties across Siesta Key, from small condos to luxury homes.

• SkyRun Vacation Rentals – Offers a variety of homes and condos across Siesta Key, with flexible options for families and groups.

• Siesta Key Luxury Rental Properties – Manages 60+ upscale rentals, including beachfront homes and villas. Concierge-level service available.

• Tropical Sands Accommodations – Over 450 properties including beach condos and family-friendly homes with full guest services.

• Beachside Management Vacation Rentals – Wide selection ranging from cozy studios to large private homes across the island.

Tips for Booking Your Siesta Key Rental

• Book early during peak season (winter and spring). Rentals fill quickly.

• Choose location wisely:

  • Siesta Village for restaurants and nightlife.

  • Crescent Beach for a quieter experience.

  • Turtle Beach for more seclusion and fishing.

• Compare amenities — pools, beach access, pet policies, and parking all vary by property.

• Read reviews for insights on property condition and management responsiveness.

FAQs About Siesta Key Vacation Rentals

What types of rentals are available in Siesta Key?

You can choose from beachfront condos, luxury villas, single-family homes, and cozy cottages.

Is it better to stay near Siesta Village or Turtle Beach?

Siesta Village offers easy access to dining and nightlife, while Turtle Beach is quieter and great for families or fishing trips.

Do vacation rentals in Siesta Key allow pets?

Many rentals are pet-friendly, but policies vary by property. Check listings for specific rules.

How far in advance should I book?

For peak seasons (January–April), it’s best to book at least 6–9 months in advance.

Siesta Key Condo Rentals

Looking for the perfect Siesta Key condo rental? From the peaceful shores of Turtle Beach to the lively energy of Siesta Key Village, the island offers a variety of accommodations to match every style and budget. Explore these top rated condo communities each offering its own unique charm, location, and amenities—for your ideal beach getaway.

Turtle Beach Rentals (South end)

• Fisherman’s Cove — 9000 Blind Pass Rd, Sarasota, FL 34242
  True Gulf-front condos at the end of Turtle Beach Park; boat docks on Blind Pass Lagoon and easy beach access.

• Turtle Beach Resort — 9049 Midnight Pass Rd, Siesta Key, FL 34242
  A charming, waterfront resort nestled on Little Sarasota Bay just a short walk from Turtle Beach. Turtle Beach Resort offers individually decorated cottages and suites with full kitchens, private patios (many with hot tubs), and direct access to kayaks, canoes, bikes, and fishing gear included for guests. With a heated pool, private docks, and calm bay views, it’s a peaceful escape that blends Old-Florida character with modern vacation comforts.

• Bay Tree Club — 8625 Midnight Pass Rd, Sarasota, FL 34242
  Classic “Gulf-to-Bay” community with private beach cabanas on the Gulf side and docks on the Bay side.

Crescent Beach (mid-island, south of Public Beach)

• The Casa Blanca — 6154 Midnight Pass Rd, Siesta Key, FL 34242
  Beachfront villas and condos right on Crescent Beach. The resort offers a large heated pool, private beach access, and a clubhouse with recreation areas. Units range from cozy one-bedrooms to spacious two-bedroom villas, each featuring full kitchens and tropical decor. Ideal for weekly rentals and family stays, just minutes from shops and dining along Midnight Pass.

• Palm Bay Club — 5960 Midnight Pass Rd, Siesta Key, FL 34242
  Large beachfront/bayside resort with private beach, pools, tennis, and fishing pier.

• Crystal Sands — 6300 Midnight Pass Rd, Siesta Key, FL 34242
  Two Gulf-front towers plus villas right on Crescent Beach; mostly 2-bedroom layouts.

• Siesta Breakers — 6480 Midnight Pass Rd, Siesta Key, FL 34242
  Gated beachfront complex on Crescent Beach with resort amenities and direct sand access.

• Siesta Dunes — 6200 Midnight Pass Rd, Siesta Key, FL 34242
  Beachfront condos with large beach deck/pavilion, pool & hot tub; easy drive to dining on Midnight Pass.

• Sarasota Surf & Racquet Club — 5900 Midnight Pass Rd, Siesta Key, FL 34242
  13-acre beachfront property in the heart of Crescent Beach with tennis, pools, and private beach.

• El Presidente — 6326 Midnight Pass Rd, Siesta Key, FL 34242
  Gulf-front condos with a heated pool and private beach access along Crescent Beach.

• Casa Mar — 6006 Midnight Pass Rd, Siesta Key, FL 34242
  Low-rise, beach-side villa community with on-site rentals; casual, toes-in-the-sand vibe.

Public Beach (near main Siesta Beach)

• Gulf & Bay Club — 5730 Midnight Pass Rd, Siesta Key, FL 34242
  Resort-style, lake-and-lagoon setting directly on Siesta Beach; multiple pools, tennis, and lush grounds.

• Jamaica Royale — 5830 Midnight Pass Rd, Siesta Key, FL 34242
  Beachfront towers and garden units with three pools, set on the sands of world-famous Siesta Beach.

• Our House at the Beach — 1001 Beach Rd, Siesta Key, FL 34242
  Across from the main public beach; lake views, pool, and quick walk to the sand.

Siesta Key Village (north end, walkable to shops & dining)

• Siesta Towers — 4822 Ocean Blvd, Sarasota, FL 34242
  High-rise on the north end with pool and bay/Gulf views; walkable to Siesta Key Village.