Osprey Vacation Rentals
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Vacation Rentals by Owner in Osprey Florida -- We have partnered directly with a major provider for By Owner Rentals, and now have the selection and value to offer our visitors searching for places to rent in Florida.
Villa in Osprey that sleeps the whole family
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.......
9.8 Star Review Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
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.......
Pet Friendly Paradise Close To Sarasota-Venice
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.......
Enjoy this Condo Hideaway Casey Key area of Sarasota Relax and Enjoy this Secret
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 Bedrooms
- Sleeps 4
Osprey Vacation Rental
Pets Allowed 
Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
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.......
Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock
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.......
A Tropical 2 Bedroom/2 Bath House w/ Pool and Dock
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 .......
Southbay Yacht and Racquet Club Retreat close to Casey Key and Nokomis Beach
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 Bedrooms
- Sleeps 5
Osprey Vacation Rental
Pets Allowed
3 Bedroom Penthouse with Stunning Sunset Views of Blackburn Bay!
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........
2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!
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.......
Just South of Sarasota Gorgeous Waterfront Condo 2 Bedrooms, 2 Baths.
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.......
Luxury Condo on the water with Intercostal view
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.......
Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
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 .......
Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025!
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 Bedrooms
- Sleeps 4
Osprey Vacation Rental
5 minutes to the BEACH! Beautiful neighborhood on intercoastal. Family friendly
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.......
Spacious 3-BR + large den condo in private, quiet luxury Casey Key area
Experience very private, exclusive Osprey like a local in this 3-bedroom condo.
The lovely space features two king beds and 2 twin beds. Guests can enjoy two bathrooms, including a jetted bathtub for a relaxing soak. A serene office area with queen pull out couch offers extra comfort and flexibility.
Take a stroll across the single lane swing bridge for a morning or after dinner/sunset walk or to the Casey Key Fish House or new Deep Lagoon Restaurant. Walk to waterski, kayak, SU.......
3 Bedrooms
- Sleeps 8
Osprey Vacation Rental
4-bedroom heated Pool house in lovely Osprey, 5 minutes to the beach
Picture yourself paddling a canoe to the Casey key fish house after you take a dip in your own large heated pool with room for your whole family to have a great time. Make dinners in the outdoor kitchen and check out the sunset at Nokomis beach 5 minutes away or siesta key beach 20 minutes away. 85 inch tv with room for everyone and dining room seats 12. 3 bathrooms to make everyone happy, the perfect place for a walk or a bike ride in serene Osprey. Your close to grocery stores, breweries and .......
4-bedroom heated pool house 5 minutes to the beach
Relax at this peaceful place to stay. The little heated pool is a big hit, outdoor kitchen and lanai is a great hang, Take a kayak to the beach bar, take a bike ride down the beautiful neighborhood or go to the beach Nokomis 5 min away siesta 15 min away. Breweries, grocery stores and Oscar Scherer park all nearby. Lots of space and fast wifi. Plenty of space for a big group to spread out. 2 master bedrooms both go out to the pool deck. We want to make this the best trip you ever have!.......
Idyllic Casey Key Beach House
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.......
Sarasota Vacation paradise!
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.......
Cozy home, pet friendly, private pool & close to beach. Minimum 60 days
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 Bedrooms
- Sleeps 5
Osprey Vacation Rental
Pets Allowed
Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis
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 .......
Cozy beach bungalow
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........
Luxurious 3/2 Waterfront Retreat in Osprey, FL!
While staying here, you will be able to walk over to Casey Key by crossing the romantic swing bridge each morning. Take in the view and sightings of pelicans, dolphins, and mullets jumping in the intercostal. You can walk over to the famous Casey Key Fish House or Deep Lagoon Seafood Restaurant. Rent a waterski jet, kayak, SUP or hire a water taxi and explore the beautiful intercostal waterways. Sit in the balcony or take a short drive down to the Nokomis Beach and North Jetty to catch a techno .......
3 Bedrooms
- Sleeps 5
Osprey Vacation Rental
Renovated Tranquil 3-Bdrm- w/ yard, workspace, great kitchen in Osprey dogs ok
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 .......
Sunny Coastal Escape
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.......
Charming Osprey Home
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 Spacious townhome in Osprey
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.......
Sarasota Home With Pool
This thoughtfully designed 3-bedroom, 2-bath home offers a refined and comfortable stay just minutes from Siesta Key and Nokomis Beach. Ideal for families and small groups, the home accommodates up to 8 guests with a layout that balances shared space and privacy.
Inside, the living area is open and inviting, flowing seamlessly into a fully equipped kitchen designed for both casual meals and entertaining. The bedrooms are well-appointed with ample storage, creating a restful environment fo.......
Condo Windsor Lodge The Oaks Unit 5 pool access
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 and 2 childr.......
1 Bedrooms
- Sleeps 2
Osprey Vacation Rental
Cozy Cottage in south Sarasota Florida, Close to Beaches!
Step inside and feel instantly at home in a space that effortlessly blends warmth, comfort, and style. Though the home is cozy, it’s overflowing with charm and character, making every corner feel inviting and uniquely delightful. Each room is thoughtfully curated with plush linens and inviting touches, ensuring a serene and restful night’s sleep. Extra pillows and cozy accents make it easy to sink in, unwind, and recharge after a day of adventure.
The heart of the home is the kitchen,.......
Windsor Lodge Unit 10, Studio, close to the beaches, pool access
Windsor Lodge at The Oaks Golf and Country Club: Luxurious, high quality furnished golf course 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 and a washing machine and drye.......
Windsor Lodge Unit 7, studio, close to the beaches, pool access
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 in 2013 and has a loft-like, architecturally designed, open concept space.
It comfortably sleeps max 2 adults (king size bed) and a max of 2 children (full size bed).
Maximum number of guests 4 persons, this number may not be exceeded even with a baby. <.......
Windsor Lodge Unit 20, studio, close to the beaches, pool access
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, kitchenette w.......
1 Bedrooms
- Sleeps 4
Osprey Vacation Rental
Windsor Lodge Unit 15, studio, close to the beaches, pool access
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 4.
On 595 sqft living space a living-, eating and sleeping area with kitchenette awaits you.
The bathroom has a sink, a walk-in shower and a toilet.
The kitchenette is equipped with a microwave, a fridge, 2 stove burners and a coffeemaker.
Dishes, glasses and cutlery are provided for 4 people.
Air Condition, .......
Windsor Lodge Unit #19, studio close to beaches
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 and .......