Pet-friendly holiday rentals in Osprey

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

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.

Sarasota Tropical Place in the Heart of the Gulf!

Forget your worries in this spacious and serene space and enjoy all the magic Sarasota has to offer. This charming home is a 3 bedroom 2 bathroom with an open light living room. Kitchen fully stocked will meet all your cooking needs. Other amenities include TV, WIFI, and gas BBQ grill with patio Chaise Lounge Chairs. A fenced in patio with lush palms.This beautiful home is the perfect getaway for friends and families that is conveniently located in the heart of the Gulfs most beautiful beaches.

Sarasota Villa 1 min to BEACH, king/qn/Pets/Yard!

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:)

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.

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!

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.

Cute Little Getaway

Close to the beach and walking distance to 5 restaurants, including one on the water. Our place is less than 2 miles from Nokomis Beach! We have you covered on beach equipment, wagon, chairs, towels and umbrella. The backyard boasts a relaxing, beautiful escape with resort style touches. We have a gas grill to cook your catch, a high powered outdoor fan, and comfy seating in the shade. The house is freshly modernized, open and airy. You will enjoy an outfitted kitchen.

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).

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!