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

Oasis Getaway -Beautiful House-Infinity Pool-Beach

Do you love the beach? Do you love lounging in a beautiful pool surrounded by palm trees and South Florida's world-renowned weather? Look no further because Sunny Oasis is waiting for you! We are located just 2 miles from the beach and 3 miles from Venice Downtown, you are choosing the right place! There is large heated Infinity pool with hot tub, spacious 1-acre courtyard with monkey bars, zip line and much more for the whole family! Make some memories at this unique and family-friendly place.

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!

Venice Beach Studio

Start your day off right with a cup of coffee watching the birds, squirrels play in our quiet backyard. You will have a private entrance and parking space as well as the entire studio to yourself. We are located 2.5 miles from the sands of Venice Beach and 2.5 miles off route 75 and downtown Venice. Enjoy all the amenities of home with Roku TV, high speed internet, queen size bed, cooking utensils, beach towels and chairs. A washer/dryer available upon request with stays of 3 days or more.

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!

Lovely Beachside Efficiency

Nicely decorated beachside efficiency perfect for a cozy couples getaway. Located in our tropical courtyard, you're just a few steps from beautiful Nokomis Beach and the heated pool. Play all day in the sun and surf and get a good night's sleep in the queen size bed. The bathroom offers a spacious shower and soft towels . The kitchen has everything you'll need for a quick meal or walk to a nearby waterside restaurant. Explore Florida's Gulf Coast and come "Home" to A Beach Retreat.

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!

Peaceful Glamorous 2 Bed Resort

This beautiful condominium is located in the heart of Sarasota, just a few miles away from Siesta Key beach, which is beach number one in the USA, and the greater areas of Sarasota. Supermarkets like Costco, Wal-Mart, Target, and Publix are near by within one mile drive. Sarasota Sharks Inc. at the Selby Aquatic Center. If it's your first time in Sarasota, you will enjoy the convenient location of this beautiful condominium. Come, relax and we hope you enjoy your stay.

Posh Siesta Key Beach Getway

March Special DISCOUNT message for details Beach home under 11 minutes to Siesta Key beach & attractions : 20 minutes to the airport 15 minutes to UTC Hammock Fire pit Foosball Backyard patio seating Grill Cozy Decor Comfy beds Fully stocked kitchen Fully stocked bathrooms Minutes to shops & restaurants Quite and safe location Escape to this beautiful home in quiet South Sarasota The perfect blend of comfort, location, and charm for your beach tea

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).

Cozy Cottage by the Bay

Enjoy this modern yet rustic looking guest cottage in historic Osprey, one of Sarasota County's first settlements. Walk to the bayfront, restaurants, shopping, library, and parks. A short drive takes you to our famous Gulf beaches and all that Sarasota and Venice has to offer. Hurricane Milton: Yes, we are cleaned up and have power and internet!

Charming Osprey Home

Your family will be close to everything when you stay in this centrally located, single-story duplex unit. Designed for families, small groups, or traveling professionals. This unit is fully furnished with all the necessities you need to make your stay relaxing and enjoyable, and some nice-to-haves, including Netflix and complimentary coffee.