Pet-friendly vacation rentals in Osprey

The Ibis Cottage

Freshly renovated, The Ibis Cottage is a cozy studio on a beautiful property overlooking a small lake. It is a 5 minute drive to Nokomis Beach, Siesta Beach and Venice Beach are within easy reach, and a block away to the Legacy Trail bike path (Sarasota to Venice). Enjoy seeing a variety of birds on the property including the ibis, heron, and snowy egret. The cottage is conveniently located between Sarasota and Venice. The perfect location for enjoying the Gulf coast and outstanding beaches.

MAR OPEN! New modern 1 min to Beach, Yard, Pets OK

Our unique villas sit just 1/2 mile from one of Florida's most pristine beaches. Biking, boating, kayaking, museums, as well as great dining/shopping are easily accessible. The villas also have an attached yard/field perfect for pets to run and exercise. Max pet weight 40 lb total. The local beach has only one access point for over 7 miles of private beach, Casey Key is a secret gem! As superhosts we love creating great memories, please read our reviews! Two adults, two kids maximum capacity:)

7 Min to the BEACH 2 King Beds Fenced yard PETS OK

Sandy Flamingo Vacations is offering this spacious and fully renovated home in South Venice, located just south of Sarasota. 2 bedrooms, 2 baths and a bonus room/game room. It is ideal for both work and leisure travel, offering a serene retreat to enjoy activities such as sunny beaches, fishing, boating and exploring. The backyard is fully fenced, featuring a BBQ grill and patio table for outdoor dining. The kitchen is fully stocked, making it suitable for long stays and family cooking.

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!

Chic & Cozy Getaway • Near Siesta Key Beach

Renovated modern studio in a duplex home with private entrance, full kitchen, bathroom, laundry, and parking. Nestled in a quiet, safe neighborhood just minutes from Lido, Turtle, Nokomis beaches, and Siesta Key—#1 beach in America with soft, white sand. Walk to restaurants, Starbucks, Total Wine, Costco, Target, CVS, Bay Village Assisted Living, Selby Aquatic Center & Vamo Bay Park. Short drive to downtown Sarasota, Venice & scenic bike trails. Ideal for beach getaways or extended stays!

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!

Sunny Oasis/Beautiful House/Near Beach/Heated Pool

Beautiful House with 3 bedrooms, heated pool, mini golf and two-car garage. Great location. five-minute drive to the beach. near shopping plazas, restaurants, and the famous Legacy Trail perfect for biking, running, and more. Situated at a dead-end in a peaceful community. Lots of outdoor space around the house with beautiful palm trees and a large patio. bicycles, board games, cornhole, a gas grill, and more at your disposal. Lots of places to visit in the Sarasota and Venice area.

Short walk to beach 4, King bed, Dog Friendly

Location Location Location! Experience island life from this 1 BR, 2nd floor condo walking distance to everything. A few steps to Venice beach, and a short walk or bike ride down the tree lined boulevard takes you to Historic Downtown Venice where you'll find, Restaurants, Cafes, and Boutiques. Pack your bathing suit, and flip flops, with all the comforts of home, and all beach gear provided, that's all you'll need here! Sofa bed also available.

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.

Creekside Paradise I

The 1970 sqft living space hosts 3 bedrooms, 2 bathrooms, an open living room with attached ‘library’, a dining area, as well as a fully equipped kitchen. From the caged pool area you have a view of the North Creek and our Boat Dock. The pool can be electrically heated and measures 32.80ft in length/13.12ft in width. You enter Creekside Paradise I thru the attached 2 car garage, where you can find the beach equipment (chairs, umbrella, cooler).

Charming vacation home, short walk to the beach

Welcome to our charming vacation home! Just a 10-min walk to beautiful Nokomis Beach and a short drive to Siesta Key, Downtown Venice, and all the area’s attractions. Inside, the home is bright, spotless, and fully stocked with essentials. Two spacious bedrooms, each with a walk-in closet and private bath for your comfort and privacy. Enjoy the patio, grill, and peaceful neighborhood. We are looking forward to hosting you!

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.