Osprey Vacation Rentals

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.......

2 Bedroom Apartment in Osprey
Sleeps 5

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 Bedroom Vacation Home in Osprey
Sleeps 8
Pet Friendly

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.......

3 Bedroom Vacation Home in Osprey
Sleeps 5
Pet Friendly

2bd/2ba condo nestled in a quiet community. This upstairs unit offers large 16ft ceilings, fully furnished open and airy space with large LR, open kitchen, breakfast bar, large screen TV, Wifi, Desk and WFH area. Private deck with a unique secluded treehouse feeling in a condo! Great walk-ability and bike-ability 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.......

2 Bedroom Condo in Osprey
Sleeps 4
Pet Friendly

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.......

2 Bedroom Vacation Home in Osprey
Sleeps 5
Pet Friendly

Exclusive Single Family Home, private, electrically heated pool, close to beaches.
3 BR, 2BA, 6 people, garden, covered outside dining area.
You will find 3 bedrooms, a living room with separate dining space and 2 bathrooms on one floor. In the living room, there is a fireplace and a Smart-TV. Free WiFi throughout the house. In the pool area you can dine and relax under a covered seating area, your food prepared directly on the BBQ next to it.
From the caged pool area you have a view of.......

3 Bedroom Vacation Home in Osprey
Sleeps 6
Pet Friendly

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 .......

2 Bedroom Vacation Home in Osprey
Sleeps 4

This meticulously designed 3-bedroom, 2 bath home presents a blend of modern elegance and coastal charm, providing the ideal 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.
Indulge in the tranquility of your private lanai or take in sunset in your front patio with views of the intercostal. The lush surro.......

3 Bedroom Vacation Home in Osprey
Sleeps 5
Pet Friendly

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........

3 Bedroom Condo in Osprey
Sleeps 6
Pet Friendly

We think you will thoroughly enjoy your stay at this comfortable two bedroom, ground floor condo with a lovely water view to look forward to. The condo features a den with a queen size sofa bed, along with two televisions for your enjoyment. The master bedroom features a king size bed, a large bathroom with a walk-in shower, dual sinks and two walk-in closets and a water view. The second bedroom features a queen sized bed, walk-in closet and direct access to the second full bath. The unit featu.......

2 Bedroom Condo in Osprey
Sleeps 6

This beautiful 2 bedroom and 2 full baths condo is overlooking the water and canals, large screened in lanai with gorgeous sunsets, unit is on the top floor, elevator, big kitchen with all you need to make your meals and a large living room. The master bedroom has a king size bed and queen size in guest bedroom. Washer and dryer is in the unit. Located between Sarasota and Venice close to beaches, boating, golfing, shopping and many excellent restaurants. The amenities of this luxurious gated co.......

2 Bedroom Condo in Osprey
Sleeps 4

Great location at Osprey Harbor Villas located at the swing bridge going onto Casey Key. Located between Siesta Key and Venice and is a great area for walking, biking, boating and kayaking. Gated, secure and quiet complex with 2 under building parking spaces. You will enjoy the well laid out 1900 sqft suite. The master bath is gorgeous with a walk in shower and double vanities. Kitchen has new appliances and lots of cabinets, counter and bar space. Island serves as dining area. Large laun.......

3 Bedroom Condo in Osprey
Sleeps 6

Bay Street condominiums are a newer complex (2017)
in a beautiful gated community right off of Tamiami trail and a quick 10 minute drive from Nokomis beach or 15 minutes from white sandy beaches world renowned Siesta Key beaches. Screened lanai overlooks a large pond. Neutral updated decor gives a relaxing feel and sleeps 6. There’s a heated community pool and an exercise facility. 1528 square feet of living area. Unit has one interior flight of stairs to enter unit. Washer .......

3 Bedroom Condo in Osprey
Sleeps 6

Decisions, decisions...which beach to go to today? Siesta Key, Nokomis, Venice, Lido, Englewood.... Or bike ride on the Legacy Trail to the beach, perhaps kayak on Little Sarasota Bay (water sport rentals avail nearby). Did someone say Siesrs Key Rum tour ?? Or the Ringling Tour? Regardless of how you choose to vacation. Enjoy morning coffee on the lanai watching birds and the sun rise above the tree line. Relax in bed gazing Florida's tropical jungle while giant butterflies float by. Grill and .......

2 Bedroom Vacation Home in Osprey
Sleeps 4

Cozy three bedroom home located in a neighborhood sitting on the intercoastal. Enjoy taking our two kayaks out on the water. We provide some family games and books that you can enjoy and maybe take onto the covered lanai to watch a beautiful sunset. Nokomis Beach (5 minutes away) and Siesta beach are very close by. Enjoy an outdoor shower in the fenced in back yard after spending a day on the white sandy beach. Yard toys are here as well. Lots of incredible restaurants are nearby without the tra.......

3 Bedroom Vacation Home in Osprey
Sleeps 8

Idyllic beachfront home located on exclusive, unique Casey Key in Sarasota, Florida.

Set in lush tropical greenery including 61 palm trees, sea grapes, and Hibiscus plants, just a few backyard steps to a white sand beach and spectacular sunsets on the Gulf of America . Walk to historic Casey Key landmarks, including its unique swing bridge and famous Casey Key Fish House and Tiki bar, or glimpse playful Dolphins from your own private beach access.

Sarasota is a cultural seat, home.......

3 Bedroom Vacation Home in Osprey
Sleeps 6
Pet Friendly

Welcome to our new coastal retreat between Siesta Key Beach and Nokomis Beach. Enjoy quick access to Costco, Walmart, Publix, and restaurants within 5 min. Sarasota downtown is just 15 min away. Launch your boat 2.5 miles from here. Inside, find modern comforts and vacation vibes. Relax in stylish living spaces, cook in the well-equipped kitchen, and sleep soundly in comfy bedrooms. Enjoy outdoor dining and lush surroundings. High-speed Wi-Fi included! Book now for an unforgettable getaway.......

3 Bedroom Vacation Home in Osprey
Sleeps 8

Your cozy getaway awaits in Osprey at this lovely house. With 2 bedrooms including a king and queen bed, 2 bathrooms with shower amenities, and an additional office space with a twin bed, this property is perfect for a couple or family. Enjoy the private pool, Clubhouse amenities of a fitness room, pickle ball and tennis courts, pool and walking trails, marina facilities, and water views of the Intercoastal waterway. Siesta Key and Nokomis beaches nearby. We are dog friendly. Great restaurants .......

2 Bedroom Vacation Home in Osprey
Sleeps 5
Pet Friendly

Located in Osprey Fl, this beautiful recently renovated condo is a dream. With 1 cozy bedroom and a lovely living room, guests will feel right at home. Enjoy the tranquil surroundings and take advantage of amenities like WiFi, AC, and a fitness room, heated swimming pools, tennis and pickelball courts, walking and biking trails. Quiet neighborhood, 2nd floor with balconies, private court yard, Does not share walls with neighbors, Heated pools, tennis and pickleball courts,

Your vacation .......

1 Bedroom Condo in Osprey
Sleeps 3
Pet Friendly

Escape to our relaxing 2-bedroom home in Osprey, Florida, just minutes from the stunning beaches of the Gulf of Mexico, pristine golf courses and MLB spring training. This peaceful retreat sleeps up to 7 adults and offers a perfect blend of comfort & convenience. The master bedroom features a queen bed and the second bedroom has a bunkbed sleep system with a queen mattress on bottom and twin mattress elevated above. There is also an office with a daybed & trundle for additional sleeping space........

2 Bedroom Vacation Home in Osprey
Sleeps 7

Home away from home while you visit Osprey, Venice, and Siesta Key attractions. This perfectly located property boasts 3 bedrooms and a fully fenced yard with lush landscaping. With 2 modern bathrooms and a fully equipped gourmet kitchen, guests will feel right at home. Enjoy the soothing atmosphere of this quaint house and all that the Sarasota area has to offer. Less than a 5-minute drive to beaches, kayak access, bars, and local fares. Garage Parking, Outdoor Dining, and Easy access to the .......

3 Bedroom Vacation Home in Osprey
Sleeps 5
Pet Friendly

Step into a sunlit, single-story home with two bedrooms and two full bathrooms. Designed for families or small groups, this 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 guests find fun things to do, un.......

2 Bedroom Vacation Home in Osprey
Sleeps 6
Pet Friendly

Relax in this stylish 2BR/2BA private unit (duplex) just 10 minutes from Nokomis Beach. Enjoy a private lanai, a fully fenced in backyard, fast Wi-Fi, full kitchen, and Smart TV with Netflix. Perfect for couples, families, or mid-term stays. Close to Siesta Key, Venice, and St. Armands. Sleeps 6 people.

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 guests find fun things to do, .......

2 Bedroom Vacation Home in Osprey
Sleeps 6
Pet Friendly

Your Osprey adventure begins at this 2-bedroom townhome. Enjoy all of the local charm and activities the Casey Key area has to offer. Our townhome is the perfect balance of ambiance and serenity, tucked away from the bustling city while also being in close proximity to stores, beaches and water front dining. Only 7 miles from the #1 rated beach in America, Siesta Key Beach and only 2 miles from the nearest boat ramp, perfectly nestled in Osprey, Fl. between Sarasota and Venice, Fl. It has an op.......

2 Bedroom Vacation Home in Osprey
Sleeps 5

Windsor Lodge at The Oaks Golf and Country Club: Luxurious, high quality furnished golf course rental with community pool.

Enjoy a wonderful view of the adjoining lake and the golf course from your patio. On 595 sqft you fill find a combined living/sleeping area with king size murphy bed, kitchen with stove, oven, microwave, toaster, dishwasher, fridge/freezer, coffee maker. The bathroom has a big walk-in shower and 2 sinks. 2 TVs and free internet. The unit accommodates 2 adults........

1 Bedroom Condo in Osprey
Sleeps 2

Unit 10 at Windsor Lodge is a cozy and functional vacation rental located within the gated community of The Oaks Golf and Country Club. This unit is ideal for guests seeking a comfortable stay in a quiet, upscale golf community close to Sarasota’s beaches, dining, and shopping.

The unit features a Murphy full-size bed in the living area, allowing the space to function as a living room during the day and easily transform into a sleeping area at night. An additional inflatable mattress i.......

1 Bedroom Apartment in Osprey
Sleeps 4

Modern, Loft-Style Studio near Siesta Key!

Completely remodeled with an architect-designed, open-concept layout, this stylish 595 sq ft apartment offers an ultra-modern feel. It features premium high-end finishes, a fully equipped kitchen (including a Liebherr fridge/freezer), and beautiful design touches throughout.

Sleeping Arrangements:

Comfortably sleeps up to 2 adults on the premium King-size bed and up to 2 children on the additional Full-size bed.

The Highl.......

1 Bedroom Apartment in Osprey
Sleeps 4

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, sleepercouch, kit.......

1 Bedroom Condo in Osprey
Sleeps 4

Unit 15 at Windsor Lodge is a comfortable and inviting vacation rental located within the gated community of The Oaks Golf and Country Club. This unit is ideal for couples or small groups seeking a peaceful stay in an upscale golf community close to Sarasota’s beaches, shopping, and dining.

The unit features a comfortable king-size bed, providing a restful night’s sleep, as well as an additional inflatable mattress for extra guests when needed. The thoughtfully arranged interior offe.......

1 Bedroom Apartment in Osprey
Sleeps 4

Unit 19 at Windsor Lodge is a charming and well-appointed 1-bedroom, 1-bath vacation rental located within the gated community of The Oaks Golf and Country Club. Surrounded by beautifully maintained grounds and a peaceful golf course setting, this unit is ideal for couples or solo travelers seeking comfort, privacy, and a refined Florida lifestyle.

The unit features an open and inviting layout with a comfortable living area that flows seamlessly into the sleeping space, creating a bright.......

1 Bedroom Apartment in Osprey
Sleeps 4

Unit 18 at Windsor Lodge in The Oaks is a comfortable 1-bedroom, 1-bath vacation unit located within the prestigious Oaks Club community. This inviting retreat is ideal for couples or small groups, offering sleeping accommodations for additional guests with a sleeper sofa in the living area. Guests also have access to the community pool, providing a refreshing option for relaxation during their stay.

The unit features bright and welcoming living spaces designed for comfort and ease. The .......

1 Bedroom Apartment in Osprey
Sleeps 4

On 595 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 entertainment for everyone, the air-conditioning (or heating) is installed with the highest standards. The kingsize bed together with the sleeping sofa are offering space for 4 .......

1 Bedroom Apartment in Osprey
Sleeps 4

Welcome to Edgewater at HIDDEN BAY COMMUNITY, offering luxurious waterfront living. This 3 bedroom 2.5 bath waterfront condo is immaculate and the perfect place for a seasonal snow bird rental, annual rental or Florida vacation (1 month minimum). Relax on the spacious lanai that reveals a view of the bay and AMAZING SUNSETS. The unit has an elegant foyer and comes with a separate laundry room with washer, dryer, sink and plenty of storage. There is a 1/2 bath off of the kitchen and a separate wa.......

3 Bedroom Condo in Osprey
Sleeps 6
Pet Friendly

Welcome to our clean and comfortable entire home, perfect for families, couples, or business travelers. Enjoy a quiet neighborhood with easy access to shops, restaurants, and major roads. The house features cozy bedrooms, a fully equipped kitchen, fast Wi-Fi, and free parking. Relax, unwind, and feel at home during your stay. Ideal for short or extended visits year-round. Book with confidence and enjoy a stress-free stay........

3 Bedroom Vacation Home in Osprey
Sleeps 10
Pet Friendly

Mid-century home located midway between Sarasota and Venice FL. Peaceful views of South creek flowing into the Sarasota inter coastal waterway. Tranquil and calming home perfect for couples or families looking to escape the daily hustle and unwind. Cool off in the pool during the day or take a dip in the evening. Kayaks available to launch off private dock. Kayak directly into Oscar Scherer State Park or the inter coastal . Manatees can be seen moving along the canal. Nokomis beach is a 10 minut.......

3 Bedroom Vacation Home in Osprey
Sleeps 6

Look no further than this private guesthouse that is a great retreat for the family. Enjoy the pool, hot tub on a nice warm day. Go swing the tennis racket on the private courts. Or take a quick drive to Nokomis Beach to lay out, catch some rays, or enjoy the water. This 3 bedroom private guesthouse will be perfect for the family vacation. Enjoy the newly renovated home with custom kitchen, waterfall showers, high speed internet and a private balcony. You will not want to miss this! .......

3 Bedroom Condo in Osprey
Sleeps 7
Pet Friendly