Holiday houses in Osprey

Venice Beach Villa/walk to beach/swimspa-pool

Location, Location! Have fun with family and friends at this stylish villa. Beautiful set up and spacious outdoor area with grill and pool with a river jet, spa jets and option of heating. Located very close to the beach (10 min walk, 3 min bike ride and 2 min car ride), less than 2 mile to downtown Venice for restaurants and shopping and less than 1 mile to the famous Sharky’s on the pier. 2 bedroom/2 bath with open concept, private lanai and centrally located. Perfect for memorable get aways.

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!

Sarasota Summer Beach Bliss!

Welcome to our serene haven in the heart of Sarasota, Florida! Our spacious 3 bed, 2-bath home offers the perfect blend of comfort, convenience, and style. Set in a tranquil neighborhood, this retreat is an ideal destination for families, groups, or couples seeking a memorable vacation in beautiful Sarasota. We are excited to welcome you to our serene Sarasota haven, where comfort and convenience await. Book your stay today and create unforgettable memories in this idyllic Florida destination!

🌺 Stunning 2 Br/2 Ba Pool Home Near Beaches

Welcome to your home away from home. This inviting, happy home is spacious, bright, comfortable, and situated in a quiet neighborhood - conveniently located to 3 nearby beaches and the historic downtown Venice. The home is newly renovated with an open floor plan and private pool. The master bedroom and en-suite has a king-sized bed. Second bedroom offers your choice of bed configuration with the option for two XL twin beds which can be pushed together to create the equivalent of a king-sz bed.

Bright & Specious Getaway • Near Siesta Key Beach

Spacious 2BR/1BA apartment just 5 miles from Siesta Key and Sarasota attractions. Pet-friendly with private entrance, screened furnished porch, fenced yard, central A/C, and laundry room. Sleeps 6. Walk to Sprouts, Costco, Total Wine, Starbucks, Target, CVS, restaurants, Vamo Bay Park, and Selby Aquatic Center. Close to beaches, bike routes, and Bay Village Assisted Living. Quiet, secure neighborhood — ideal for families with kids, travel nurses, and snowbirds seeking comfort and convenience.

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!

Cozy Beach Cottage

Welcome to your peaceful retreat just 3.3 miles from Casey Key Beach and 5 miles from the Myakka River. Enjoy your private dock on Shackett Creek just a block away, or explore The Legacy Trail less than a mile from your door. Downtown Venice is only 3.5 miles away with great dining and shopping . Spend your days hunting for fossilized shark teeth, kayaking, biking, or relaxing at home by the outdoor fire pit. Whether you’re here to unwind or explore, Nokomis is a nature lover’s paradise!

Pineapple and Palms

This beautiful home is located in the best neighborhood in Nokomis with a fishing hole and 2 kayak launches into the bay! The attached guest house offers its own entrance, driveway and fenced yard located less than 1 mile to Nokomis Beach and Casey Key and 2 miles to Venice Island. Includes everything you need to relax in Paradise! Coffee on the porch, kids or dogs safe in the fenced yard. Kayaking, walks, serene biking on Legacy trail. That's Life here, come join!

Viva life Residence

Relax with the whole family at this peaceful place to stay.Enjoy the Nature at the spacious back yard . Just 6 min to the beautiful Nokomis beach, where you can enjoy an unforgettable sunset. A few min away you can visit the beautiful Osca Sherer State Park where you can do various outdoor activities such as: walking its trails, fishing, kayaking, etc. We have the best local bars/restaurants 5 minutes from our residence.Enjoy you stay at Viva Life Residence

Great location! Updated & loaded with all you need

Looking for great location for vacation…This coastal 2 BR/2 Bath remodeled home is located in a great neighborhood and close to everything that you would want to explore. Within minutes of Siesta Key, Casey Key, Venice Beach and famous Shark Tooth Caspersen Beach. Only an hour from Tampa, within minutes of all the amenities and shopping you could want. After a day of fun, return to a cozy, clean and comfortable home where you can relax and unwind.

Coastal 3BR Getaway|5 Min to Beach|Pool+Peloton

Welcome to the Nokomis Pearl—your serene beach retreat just five minutes from the sun-drenched shores of Nokomis Beach! This stylish 3-bedroom, 2-bath getaway offers the perfect blend of comfort, charm, and luxury coastal living. Inside, you’ll find a spacious, beautifully furnished living area and a fully equipped modern kitchen ready for home-cooked meals or casual snacks.

Terrific Treehouse by the Bay

Enjoy this modern yet rustic looking second-floor guest cottage in historic Osprey, one of Sarasota County's first settlements. Walk to the bayfront, restaurants, shopping, library, and parks. A short drive takes you to our famous Gulf beaches and all that Sarasota and Venice has to offer. Hurricane Milton: Yes, we are cleaned up and have power and internet!