Holiday rentals with a patio in Osprey

Close to Beaches~ Downtown Venice~Bike Trail~Park

This cozy NEW home is located across the street from Nokomis Community Park; which includes pickleball and tennis courts, kayak launch, fishing pier and access to the Legacy Bike Trail. Only 2 miles to Nokomis Beach and Casey Key and 3 miles to Venice Beach. Downtown Venice is only 2 miles away - perfect for shopping and dining. Less than 4 miles to Fox Lea Farm- a horse show facility. Parkview Cottage is the perfect mix of comfort, convenience, and fun for families, couples, or small groups.

5 mins to the beach! Come relax!

Relax with the family at this peaceful place to stay. Home located in a unique family friendly neighborhood on the inter-coastal. Enjoy family games, watching the sunset from the lanai and using the enclosed outdoor shower after a day at the white sandy beach! Take out our 2 kayaks on the intercoastal and explore the area. Nokomis beach 5 minutes away and Siesta key 7 miles. So many cute restaurants nearby on the water. Stroll through the neighborhood and see all of the beautiful homes and boats

Pet-Friendly Modern Retreat Near Siesta Key

Discover your perfect Florida retreat in this stylish, spacious, and pet-friendly home located in a quiet Palmer Ranch neighborhood. Enjoy an open-concept layout with tall ceilings, a fully stocked modern kitchen, luxury linens, and a fenced-in yard ideal for pets and families. Centrally located near beaches, shops, golf, and top attractions, this elegant getaway offers comfort, convenience, and relaxation. Perfect for extended stays, remote work, and unforgettable family memories all year round

Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

Nokomis & Siesta Key Sand Dollar Retreat

Escape to our relaxing 2-bedroom home in Osprey, Florida, just minutes from the stunning beaches of the Gulf of Mexico, pristine golf courses and MLB spring training. This peaceful retreat sleeps up to 7 adults and offers a perfect blend of comfort & convenience. The master bedroom features a queen bed and the second bedroom has a bunkbed sleep system with a queen mattress on bottom and twin mattress elevated above. There is also an office with a daybed & trundle for additional sleeping space.

Saltwater Oasis

Welcome to your dream vacation home, where the tranquility of a private saltwater pool meets the convenience of a prime location, just minutes from Nokomis Beach, Legacy Trail and Siesta Key, the USA's #1 Beach. This home offers the perfect blend of comfort, style, and relaxation for your getaway. Our home even features a King sized master bedroom equipped with a sleeper sofa, ensuring young children can stay close to their parents. This is your haven for creating unforgettable memories.

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Welcome to our beautiful condo, which is located just 4 miles to Siesta Key! Enjoy Vamo Park, just steps from our door, where you can launch a kayak or paddle board. Fishing is also allowed from this location. There are also picnic tables at the park where you can enjoy sunset. Our condo is fully equipped with all the necessary things you need. Beach chairs, shops, theaters, gyms, and the legacy trail, Sarasota Sharks Inc. Plus more. These are just a few of the things available in the area.

Welcome to Paradise Palms! Canal home/Pet friendly

Canal front home in Nokomis, right next to Legacy Trail. Bicycles and Kayaks available to enjoy a trip to the beaches and local islands, please sign waivers before using and send to hosts. Fish right off your dock and enjoy covered Lanai with outdoor fireplace. Nokomis beach (2 miles), Venice beach (2.5 miles), Jetti beach (3 miles). Close to restaurants and historical Venice shopping. This home can sleep up to 8 people. Pets are welcome (125$ pet fee) Please be courteous noise late night.

Private Coastal Getaway - Your Home Away from Home

Enjoy privacy, luxury, and comfort in this 2-bed, 1-bath coastal guesthouse, perfect for business trips or extended stays. Accommodating up to 4 guests, it features a leather Reclining Sectional, two Queen Beds with storage, and a Private Outdoor Space with seating and a Blackstone grill. Located in Osprey, FL, you're ideally situated between Siesta Key, Nokomis, and Venice beaches—just minutes from sand and sun! Set down your bags and grab complimentary beach chairs, umbrella, and cooler!

Mattie’s Cottage by the Bay

Enjoy this 1913 Florida vernacular cottage! Carefully restored, thoughtfully updated house on a quiet, tree-canopied street in historic Osprey, one of Sarasota County’s oldest settlements. Enclosed front porch, screened back porch, and tin roof. Walk to the bayfront, restaurants, shopping, library, parks, and historic sites. A short drive takes you to famous Gulf beaches and all Sarasota and Venice have to offer. Hurricane Milton: Yes, we are cleaned up and have power and internet!

Private house with loft

Have fun with the whole family at this brand new, modern private free standing guest house. Full bedroom with king size bed, with a finished loft including a queen bed. There’s also a queen pull out sofa in the living area. Enjoy your privately fenced backyard with a hot tub and putting green. Centrally located between Siesta Key beach and Nokomis beach. Hot tub is available upon request in off season months, April-October. There will be an additional $30 fee in off season months.

Heated Pool • Lakeview Escape • Near Nokomis Beach

Welcome to Lakeview Escape, a peaceful Nokomis townhouse with beautiful lake views, just 7 minutes from Nokomis Beach and with direct access to the Legacy Trail. Enjoy a relaxing stay with fast Wi-Fi, a resort-style community pool, and a comfortable space perfect for families, couples, remote work, and pet-friendly travel. Whether you're here for beach days, biking, or a quiet getaway near Sarasota and Venice, this home offers the perfect balance of location, comfort, and ease.