Pet-friendly holiday rentals in Osprey

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

Outdoor spaces · Pets · Check-in

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

Welcome to The Salty Unicorn, your cheerful Sarasota escape just five miles from Siesta Key Beach. This fully renovated 3-bedroom home is designed for relaxation and fun, with a bright open layout, stylish coastal décor, and plenty of space to gather with family or friends. Start your mornings with coffee by the pool, spend sunny afternoons swimming or lounging in the spacious backyard, and end the day with dinner in the screened lanai. Whether you’re here for beach days, family time, or a peace

Pets · Outdoor spaces · Air conditioning

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:)

Pets · Walkability · Getting around

Great one bedroom apartment near beaches in Osprey

Our rental features a one bedroom with an attached living room and private bathroom. The bedroom offers a queen bed, walk in closet. The living room has a large couch and tv. Full equipped kitchen with a laundry room. The apartment has its own private front door entrance and driveway parking. Friendly for dogs to safety run outside (gated). The house is located 12 min away from Siesta Beach (ranked #1 in Fl) and 10 min away from Nokomis Beach. We are placed between Venice and Sarasota. WiFi

Walkability · Pets · Heating

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.

Outdoor spaces · Pets · Getting around

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!

Pets · Outdoor spaces · Value

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.

Outdoor spaces · Pets · Parks

2 BR House 1.6 miles from Siesta Key Beach

Discover the charm of Sarasota in our newly remodeled 2BR/1BA vacation home. Just 1.6 miles from beautiful Siesta Key Beach! Enjoy your morning coffee on a brick patio surrounded by flowers and sunshine. Our comfy beds, blackout curtains, and quiet neighborhood ensure a sweet deep sleep. FIOS wifi and three smart TVs; a fully-equipped kitchen; and a sparkling new bathroom with two sinks, huge mirror, and marble shower offer all the comforts and convenience of home. We welcome you!

Pets · Walkability · Backyard

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.

Walkability · Outdoor spaces · Decor

Tiki Oasis 3bed on .6 acre paradise 5 min to Beach

Relax with the whole family at this peaceful place to stay. Enjoy 2 master suites with 3 bedrooms and 3 bathrooms. A 5 min drive to Nokomis beach or downtown Venice, and walking distance to legacy trail, tennis courts, and playground in Nokomis park. Fast 500GB up/down internet speed around the property, Tiki bar nestled next to a heated pool and spa ( adtnl charge for spa). Fully stocked kitchen, beach-ready with cooler chairs umbrella wagon, and toys. 4 smart tvs

Walkability · Outdoor spaces · Family

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).

Outdoor spaces · Pets · Cleanliness

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!

Outdoor spaces · Pets · Decor