Osprey Vacation Rentals

Apartment in Osprey

Enjoy memorable sunsets, with a private view and revel in all the local charm and activities the Casey Key area have to offer. Our villa has the perfect balance of ambiance and enjoyment you are looking for in your vacation to the Sarasota/Venice area. Only 7 miles from the #1 rated beach in America, Siesta Key Beach and 2 miles from the nearest boat ramp, perfectly nestled in Osprey, Fl between Sarasota and Venice. It has an open floor plan with a large open kitchen, dining and living room per.......

4.8 Star Review

Private Vacation Home in Osprey

The house is located in a quiet neighborhood in Osprey, just south of Sarasota. The upscale layout of the house features a large master bedroom in the right wing of the building with a large walk-in closet, a bathroom equipped with an oversize twin-shower and a bathtub with build-in whirlpool. The other three bedrooms are located in the left wing. The oversize living area is equipped with leather couches, The fully equipped kitchen is open to the living area just separated by a kitchen bar. Ther.......

4.5 Star Review

Private Vacation Home in Osprey

Summary:
Step into a sunlit, single-story retreat with two inviting bedrooms and two modern bathrooms. Designed for families or groups of friends, our home seamlessly blends comfort with elegance. Located just moments away, dive into the vibrant St. Armand's Circle or unwind on the pristine sands of Siesta Key and Nokomis Beaches.

The Space:
As hosts, we've ensured this space includes everything needed for a quality and memorable experience for up to 6 guests. We love helping our gu.......

4.0 Star Review

Private Vacation Home in Osprey

Absolutely the best value for your vacation dollar in the Sarasota-Osprey-Nokomis-Venice area! This pet friendly paradise is a single family 3 bedroom-2 bath home with heated pool that has it all. Large, extremely well equipped kitchen with double ovens, cooktop island, and granite countertops. Both bathrooms are newly remodeled, travertine floors throughout, fresh linens and towels, freshly painted inside and out....topped with tasteful tropical decor. This home provides a serene, private s.......

4.8 Star Review

Condo in Osprey

If peace, natural beauty, tranquility, nearby beaches, and physical activity are what you are looking for then this is it!

Feel the sultry tropical gulf breezes while enjoying reading a book in the serene private inner courtyard, listen to the crickets at night while gently swaying in your hammock on the lanai, take a dip in one of 2 pools (one of them geothermal), play a game of tennis, kayak the Intracoastal waterway, ride your bike along the Legacy Trail or to Casey Key where you’ll.......

2 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Private Vacation Home in Osprey

Welcome to Casey Key of Siesta ! This luxurious, newly remodeled 2,900 sq. ft. Osprey home will offer you the most splendid stay, right in the heart of comfort. We are just across from the beautiful Casey Key

Our home’s curb appeal is unlike any other! When staying with us, you’ll find yourself in the midst of splendor. The private, covered swimming pool and spacious lawn makes this 5 BR/3.5 bath house a perfect fit for family vacations. Beautiful tropical Mango tree and red flambo.......

5 Bedrooms - Sleeps 8
Vacation Rental in Osprey

Condo in Osprey

2bd/2ba condo nestled in a quiet community. This upstairs unit offers large 16ft ceilings, newly decorated and updated LR/Kit Combo with breakfast bar, large screen TV, Wifi, Private deck and lots of light. Great walkability and bikeability with the bike trail nearby. Walk to the gulf, restaurants, kayak/paddleboard rentals, stores, sunset cruise, etc. Community offers 2 pools, tennis, pickleball, gym, walking paths and a gorgeous sunset over the gulf. .......

2 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Private Vacation Home in Osprey

House share with a professional female for female. Welcome to the gem on the coast enjoy the many peaceful beaches!
Located Close to beaches. Close to public golf, public tennis courts a few blocks away, and local kayaking, biking distance to restaurants on the water(Casey Key fish house, The Point). Biking on the Legacy Trail adjoining. Tennis/basketball courts and track field county park located just two blocks away. Siesta Beach 18 minutes, downtown Sarasota and St. Armonds 20 m. drive. SR.......

4.0 Star Review

Private Vacation Home in Osprey

Welcome to LIME ON GREEN! CLEAN! Entire 2, 1 home centrally located between Sarasota & Venice. Siesta Key & Nokomis Beach are less than 6 miles away. Casey Key < 2 miles away. WIFI & smart televisions in each room. Washer & dryer located in garage. The kitchen has everything you need! Neighborhood is peaceful, friendly & pet friendly! New Bay Steet Dog Park is located within walking distance. We also have a Ford Focus that you can rent. Check it out on Turo. Host lives near & is available 24/7 s.......

5.0 Star Review

Private Vacation Home in Osprey

Enjoy an effortless stay on Florida’s Gulf Coast when you book this beautiful home in Osprey! You’ll have access to bikes, kayaks, and more at this 2-bedroom, 2-bathroom vacation rental. The local kayak launch is just a short walk away, so you can easily paddle into nearby Oscar Scherer State Park! When the beach calls your name, head 4 miles south to Nokomis Public Beach where you can swim, explore, and lounge in the sand. Keep the evening low-key with dinner and a drink on the covered pati.......

2 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Private Vacation Home in Osprey

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 is electrically and solar 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, 2 bikes as well as 2 kayaks........

3 Bedrooms - Sleeps 6
Vacation Rental in Osprey

Private Vacation Home in Osprey

A brand new 3 bedroom 2.5 bath custom smart home awaits you in beautiful Sarasota, FL. Quiet neighborhood. Located in the heart of Palmer Ranch Osprey FL, between Stonybrook Golf Club and Oaks Country Club. Right across the street Historic Spanish Point. Less than ten minutes south Casey Key Beach and north Downtown Sarasota and Siesta Key Beach. This unique, tropical paradise awaits you in beautiful Sarasota, FL Ideal for groups of families & friends. Covered Lanai patio with outdoor furniture........

5.0 Star Review

Villa in Osprey

Intercoastal, Blackburn Bay waterfront home with boating facilities near Casey Key and Siesta Key. On a point facing the setting sun. This is simply paradise.

The pier is long, and the water deep enough to handle most boat docking needs. The large, heated pool is a few steps from the screened lanai and the deck beckons "come watch the sunset". And while it won't replace one of the large beaches on the key, you can lay or play on our beach hidden by mangroves, and easily launch kayaks, et.......

4.4 Star Review

Private Vacation Home in Osprey

Beautiful, 4 bedroom, 2 bath home minutes from Siesta Key
Heated pool, play structure, bikes, and canoes available.
Located in a quiet neighborhood 3 mins away from a canal access, perfect for canoeing........

4.7 Star Review

Private Vacation Home in Osprey

Relax in private secluded luxury. Lush, ornamental plantings surround the beautiful backyard and pool deck. Spacious and private, the backyard features a covered lanai, open pool and spa and outdoor shower.

Patio deck includes outdoor grill area. Exterior lighting provides beauty and ambiance for evening entertaining or relaxing.

Coconut palms abundant with fruit overhang pool deck for tropical filtering of sun.
Jasmine, Frangipani, Bird of Paradise, Bougainvillea and .......

5.0 Star Review

Private Vacation Home in Osprey

We have a beautiful brand new home available for you and your family which is perfectly located in between siesta key Beach and Nokomis Beach a highly desired area. The house is conveniently located near costco, Walmart, publix and a variety of restaurants all within 5 minutes while also being within 15 minutes from the Sarasota boardwalk/downtown area. The interior of the home has brand new furniture and a comforting vacation theme with modern style.

The space
The home was built in 20.......

3 Bedrooms - Sleeps 9
Vacation Rental in Osprey

Apartment in Osprey

Modern and stylish furnished apartment in the Windsor Lodge at The Oaks. Beautiful bath, kitchen and patio with view towards the lake and golf course. Gated community.
This particular unit has 595 sqft and was completely remodeled and has a loft-like, architecturally designed, open concept space. It comfortably sleeps 4, has a complete, fully equipped kitchen with high-end finishes (Liebherr fridge and freezer), numerous design touches, and an ultra-modern feel. The bathroom has a double sink.......

1 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Apartment in Osprey

Luxurious apartment with fabulous lake view at the Windsor Lodge. Large living-/bedroom with kitchenette, sep. bath, community pool, sleeps 2 adults and 2 children.
On 520 sqft living space a big living-, eating and sleeping area with kitchenette awaits you. The bathroom has granite counter tops, a sink, a huge walk-in shower and a toilet. The kitchenette is equipped with a microwave, a fridge and a coffee maker. Dishes, glasses and cutlery are provided for 4 people. The TV provides entertai.......

1 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Apartment in Osprey

Windsor Lodge at The Oaks Unit #15: Quiet condo with living-/bedroom, kitchenette, separate bath, pool and a beautiful view of the lake, pool and golf course - sleeps 2 people.
On 549 sqft living space a living-, eating and sleeping area with king size bed and a kitchenette awaits you. The bathroom has a sink, a bathtub shower and a toilet. The kitchenette is equipped with a microwave, a fridge, 2 stove burners and a Keurig coffeemaker. Dishes, glasses and cutlery are provided for 4 people. A.......

1 Bedrooms - Sleeps 2
Vacation Rental in Osprey

Apartment in Osprey

Luxurious, beautiful golf course rental, in the gated community of The Oaks Golf and Country Club. Open living room and bedroom, with separate bathroom. Community Pool.
On 580 sqft living space with stunning lake- and golf course views, an open space living- and sleeping area, as well as a separate bathroom, awaits you. The kitchenette is equipped with a fridge, microwave, hotplate and coffee maker. Dishes, glasses, cutlery are provided for 4 people. The TV provides entertainment for everyon.......

1 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Condo in Osprey

Luxurious, beautiful golf course rental with stunning views, in the gated community of The Oaks Golf and Country Club. Community Pool.

On 580 sqft living space with stunning lake- and golf course views, an open space living- and dining area, a separate bedroom as well as an en-suite bathroom, awaits you. The kitchenette is fully equipped: Fridge, Stove, Dishwasher, dishes, glasses, cutlery are provided for 4 people. The TV provides entertainment for everyone. The air-conditioning is inst.......

1 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Apartment in Osprey

Windsor Lodge at The Oaks Golf and Country Club: Luxurious, high quality furnished rental, fabulous lake views. Large living-/bedroom with kitchenette, separate bath, covered patio, washer/dryer and pool.
Completely furnished studio with a wonderful view of the adjoining lake and the golf course behind it. On 680 sqft living space a living-, eating and sleeping area awaits you. The bathroom has 2 separate sinks, a walk-in shower, a toilet, a washing machine and dryer. The kitchenette includes.......

1 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Condo in Osprey

Windsor Lodge at The Oaks Golf and Country Club: Luxurious, high quality furnished golf course rental, fabulous lake views. Separate bedroom, living room with kitchenette, separate bath, covered balcony, washer/dryer within unit and community pool.

Light and bright, furnished apartment with a wonderful view of the adjoining lake and the golf course from your private balcony. On 623 sqft living space a separate bedroom with king size bed, living - dining room, kitchenette with stove, oven,.......

1 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Condo in Osprey

Spectacular sunset views from this completely renovated and elegantly appointed 3 bedroom plus den condominium. Incredible location just east of Blackburn Point Bridge leading to prestigious Casey Key Road. Just 5 minute drive, golf cart or bike ride to Nokomis Public Beach. This elegant building is located next to the fabulous new Deep Lagoon Restaurant and across the road from the famous Casey Key Fish House. We just purchased in April and are looking forward to having great reviews this seaso.......

3 Bedrooms - Sleeps 8
Vacation Rental in Osprey

Private Vacation Home in Osprey

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. .......

1 Bedrooms - Sleeps 6
Vacation Rental in Osprey

Condo in Osprey

This newly constructed property (2017) is located within a small gated enclave that offers resort style pool, club house, and fitness center. The property is located a stones throw from a local park and around the corner from a major shopping center.

Enjoy nearby access to Ospreys historic Spanish Point offering serine nature walks through lush tropical waterfront landscapes. Drive to exclusive Casey Key to enjoy the ocean views; minutes to Venice Beach, Nokomis Beach or world-famous Sie.......

4.8 Star Review

Private Vacation Home in Osprey

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 Flor.......

2 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Private Vacation Home in Osprey

***Please note home is in the process of being furnished. New photos will be published once the furnishing is complete.
This meticulously designed 3-bedroom, 2 bath home presents a blend of modern elegance and coastal charm, providing the ideal winter retreat.
The home features a large stone fireplace and wood beams in the family room which is open to the kitchen. The kitchen offers all new stainless steel appliances, quartzite counters, ample cabinetry for the culinary enthusiast.
In.......

3 Bedrooms - Sleeps 5
Vacation Rental in Osprey

Condo in Osprey

SORRY RENTED JAN. FEB. AND MARCH 2022. AVAILABLE DECEMBER 2021 and APRIL 2022. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer and dryer inside unit. Nicely renovated with closet barn .......

2 Bedrooms - Sleeps 4
Vacation Rental in Osprey

Private Vacation Home in Osprey

Comfy cozy cute private drive studio with queen bed. Small fridge, coffee maker, toaster oven and microwave if you decide to cook. SHORT DRIVE to SIESTA KEY BEACH ? AND NOKOMIS ? BEACH. Very close to grocery and restaurants. We have everything you need for a fun day at the beach. Come and enjoy you stay in a quiet neighborhood. PLEASE READ THE DETAILS IN ALL THE PICTURES. Last picture keyless entry instructions.


KEYLESS ENTRY IS VERY SENSITIVE TO TOUCH! key available Steps
1........

4.6 Star Review

Private Vacation Home in Osprey

Outstanding water front views! Tall swaying palms. Heated hot tub/Infinity Pool. Fish, explore the canals, and intercoastal right from your back yard. At end of cul-de-sac this Sorento Shores home is the perfect get away! Use the kayaks, paddleboard, and bicycles. 3 mi to Nokomis beach, 5 mi to Venice Jetty, 10 mi to Siesta Key.

Beautiful oversized lot at end of cul-de-sac. Extra large lanai with tropical plants. Outstanding water views. Oversized garage with 4 bicycles, 4 kayaks and a pa.......

3 Bedrooms - Sleeps 8
Vacation Rental in Osprey

Condo in Osprey

Relaxed yet refined, this 3-bedroom Penthouse embodies a laid back attitude and care free state of mind . Get sun-drenched by the pool or enjoy a friendly tennis match on private courts. Entertaining is effortless in the fully upgraded spacious and open kitchen. 5 minutes to Nokomis Beach. 15 minutes to Siesta Key. 1 minute to Publix or Walmart. Both Master Bedrooms feature king beds and guest bedroom a queen bed. Washer/Dryer is in home........

3 Bedrooms - Sleeps 6
Vacation Rental in Osprey

Condo in Osprey

Relaxed yet Refined, this 2-bedroom condo embodies a laid back attitude and care free state of mind. Get sun-drenched by the pool, or enjoy a friendly tennis match on private courts. Entertaining is effortless in the fully upgraded spacious and open kitchen where even a casual get together becomes memorable. 5 min to Nokomis beach, 15 min to Siesta Key Beach. 1 min to Publix or Walmart. Master features king bed and guest bedroom a queen bed. Washer Dryer is in unit........

4.4 Star Review

Condo in Osprey

Sparkling pool view, tennis courts, and ample open space on Blackburn Bay. 2 Oversized Master EnSuite with King sized bed, walk in closet, and private access to enlarged screened patio. Dedicated garage parking space in building with direct access to elevators. Enjoy exquisite finishes in this tastefully renovated condominium. Large Enjoy sunsets every night on the screened in Balcony. There is no better peaceful quiet location to spend the season in style........

5.0 Star Review

Private Vacation Home in Osprey

Summary:
This amazing new listing offers 2 bedrooms and 2 bathrooms, perfect for a relaxing getaway with family or friends. Inside, you'll find a spacious and well-appointed living area with comfortable furnishings and all the amenities you need to make your stay comfortable. In the area, you'll find a variety of exciting experiences such as The St. Armands Circle shops, nightlife, and Nokomis Beach.

The Space:
As hosts, we've ensured this space includes everything needed for a qual.......

2 Bedrooms - Sleeps 6
Vacation Rental in Osprey

Condo in Osprey

New listing available from FEBRUARY 1ST, 2023. If you are looking for the perfect Florida lifestyle, romantic get away, this is it.
Conveniently located between Sarasota and Venice, #1 Siesta Key beach close by, minutes to Nokomis Beach and Jetty, Venice downtown, golf and Legacy Bike Trail .
This darling two-bedroom, two-bath, impeccably maintained is waiting for you.
Located on the second floor with a one-car garage, this condominium features a light and bright feel and has an ope.......

4.0 Star Review