Vacation rentals with a patio in Osprey

Sunshine Cottage

Our Sunshine Cottage is clean, quiet, and all yours! Enjoy the calming views of this beautiful property from your patio. It is located off a main road that takes you to Nokomis Beach in 5 minutes. Ideal for those who enjoy going to the beach, looking for shark teeth and shells. Conveniently located between Sarasota and Venice, it is the perfect place to sightsee, shop and enjoy great local food. Just around the corner from Oscar Scherer State Park and within walking distance of the Legacy Trail.

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!

The Nautilus Casita

A cozy spot to unwind the day after enjoyingTiki Bars, beaches and all Sarasota has to offer. We are 6 minutes from the Gulf and its white sandy beaches. Enjoy fishing the Jetty, boating the ICW, biking Legacy trail and enjoying sunsets at the Tiki bars with a famous grouper sandwich. So many activities to choose from in this town nestled next to the nation's #1 beach destination, Siesta key. All pets MUST be on a vet approved flea medication & proof sent prior to check in. No exceptions.

Casey Key, Gulf Coast Gem, 4 Bedroom Private Pool

Bright and Sunny Gulf Coast Getaway, Welcome to Gulf Dream, property offers 4 bedrooms, 2 full bath rooms a washer and dryer as well as plenty of room to enjoy the screened in Lanai and in ground pool, located in a quiet serene Casey Key neighborhood, Ocean breezes, and lots of sunshine, and various fruit trees this property is located just minutes from Venice Beach ( Shark Tooth Beach) 9 minutes, Nokomis Beach, (Just 8 minutes) and Siesta Key Beach (12 minutes away) #1 Beach in the USA

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Welcome to our beautiful condo, which is located just 4 miles to Siesta Key! Enjoy Vamo Park, just steps from our door, where you can launch a kayak or paddle board. Fishing is also allowed from this location. There are also picnic tables at the park where you can enjoy sunset. Our condo is fully equipped with all the necessary things you need. Beach chairs, shops, theaters, gyms, and the legacy trail, Sarasota Sharks Inc. Plus more. These are just a few of the things available in the area.

Cozy Guesthouse in central Sarasota!

This cozy independent guesthouse is perfect for all ocations from a few business day stay to a vacacion getaway. Near to siesta key beach! Enjoy a private room with a comfortable bed, a bathroom with a great shower and hot water, plus a cozy bar-style area perfect for preparing snacks and coffee. You’ll also have access to a small patio where you can unwind, and we provide beach essentials. Perfect for travelers seeking comfort and peace, and a well-equipped space. We’d love to host you!

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!

Tropical Pool Paradise - Minutes from the Beach!

Welcome to your own slice of paradise! This beautifully updated and completely eco-friendly and HEATED pool home in a quiet neighborhood is the perfect setting for your relaxing Florida vacation! You will love the privacy of this home overlooking tropical landscape vistas from the large covered lanai and solar heated pool welcoming you to your PRIVATE OASIS. You will enjoy easy access to our gulf coast beaches just minutes away. Beautiful Nokomis public beach is a 7 minute drive away.

Mattie’s Cottage by the Bay

Enjoy this 1913 Florida vernacular cottage! Carefully restored, thoughtfully updated house on a quiet, tree-canopied street in historic Osprey, one of Sarasota County’s oldest settlements. Enclosed front porch, screened back porch, and tin roof. Walk to the bayfront, restaurants, shopping, library, parks, and historic sites. A short drive takes you to famous Gulf beaches and all Sarasota and Venice have to offer. Hurricane Milton: Yes, we are cleaned up and have power and internet!

Private house with loft

Have fun with the whole family at this brand new, modern private free standing guest house. Full bedroom with king size bed, with a finished loft including a queen bed. There’s also a queen pull out sofa in the living area. Enjoy your privately fenced backyard with a hot tub and putting green. Centrally located between Siesta Key beach and Nokomis beach. Hot tub is available upon request in off season months, April-October. There will be an additional $30 fee in off season months.