Pet-friendly vacation rentals in Osprey

Modern Private Apartment 1 Block from Sarasota Bay

One block from Sarasota Bay - completely remodeled and fully furnished guest apartment with a Miami deco feel. The unit is a little over 300 sf with full kitchen, one bathroom w/ shower, comfy queen bed, several stools/ chairs, flat screen tv, wifi, off-street parking, six USB ports for easy charging and sitting area outdoors on front porch. Five minutes to downtown or SRQ airport, 15 minutes to Lido Beach, and 25 minutes to Siesta Beach with easy access to University Parkway or Fruitville Rd.

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

Garage to a Tiny House Studio Near Shopping Center

Experience comfort and style in this charming, pet-friendly space, perfect for short getaways. Enjoy the privacy of your own entrance, along with a full shower, cozy living room, dining area, and bedroom, all within one convenient layout. The fully fenced backyard, shared with other tenants, features a grill and fire pit—ideal for relaxing evenings outdoors. While the space includes a kitchenette, access to the main shared house may be available if you need a full kitchen or laundry facilities.

JAN SALE! 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:)

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!

Sweet, pet friendly Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

The Lake View

The Lakeview is a cozy independent apartment with a separate entrance and its very own screened in breezeway. The apartment is bright and airy and decorated with fresh coastal Florida colors. Located on a beautiful property overlooking a small lake, It is tucked back from a main road that will bring you to Nokomis beach in five minutes. A short drive to Siesta Beach, Sarasota, and Venice. Around the corner from Oscar Scherer State Park, and walking distance to the Legacy Trail bike path.

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!

Cozy Studio - quick walk to #1 Siesta Key Beach!

Recently renovated and updated! Adorable studio just steps from Siesta Key Village, and a quick walk to the beach. Spend your day exploring the key, swimming in the ocean, and experiencing the local restaurants and shops. Enjoy coffee in the mornings on the patio, and use the available bikes to catch a beautiful sunset each night. **Please note: - No excessive noise or Parties/Events will be allowed** - No Smoking inside the unit** - Quiet hours from 10 PM to 7 AM**

Private Suite • 10-Min Walk to Siesta Beach, Shops

🌴 Welcome to Your Cozy Siesta Key Getaway Relax in this private, well-appointed pied-à-terre located in a quiet, walkable neighborhood, just a 10-minute (0.5 mile) walk to Siesta Beach Access #12. . Perfect for couples or solo travelers looking for a comfortable, convenient home base near it all. The kitchenette is ideal for light cooking/reheating, and includes: Microwave, Refrigerator, Keurig Coffee maker, Teapot Small stove/oven, Basic dishware and utensils

Modern Studio · 5 min from Siesta Beach

Stylish ground-floor studio designed for couples or solo travelers, just a 5-minute drive from world-famous Siesta Key Beach. A great choice if you’re looking for a calm, well-located space with thoughtful comfort. Pet-friendly stay – $10 one-time pet fee per booking, unlimited pets. An ideal base for beach days, local dining, or a relaxed Florida getaway. About 1 mile from the property, guests may also enjoy access to a beautiful community pool that is heated.

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.