Vacation Rentals By Owner In Osprey, FL

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 setting with no neighbors on either side, located between golf courses and state park property. Yet with all this privacy you are only one mile from Publix grocery, CVS, WalMart, post office, restaurants, ...even Costco is just 2 miles away! This tropically landscaped paradise features screened in heated pool, outside sitting area, large flat screen TVs ....even beach chairs, coolers, and umbrellas for your trips to Siesta Key Beach, approximately seven miles away.brTo complete your stress free vacation have the added peace of mind knowing that we are 17 year veterans in the vacation home rental business. We know how to make the rental process seamless and enjoyable, handling every question and request you may have....even down to local restaurant advice. We are local owners so if you have any questions at all about our property, feel free to contact us. Other features of our house include:br br*Electronic entry system....no keys to worry about returning.br*Simply the best cleaning professional in the area...spotless upon your arrivalbr*Pool professionally cleaned and maintainedbr*Direct cell lines to owners for any questionsbr*High speed Internetbr*”Smart” TV in the living roombr*Outdoor gas grill by poolbr*Weekly yard and pool maintenancebr*Beach chairs, umbrellas, and coolers brbrWe offer 30 day rentals. brbrOur winter rates start 11/1 and end 4/30.brThe monthly rate is $5000brbrThe spring, summer, and fall rates start 5/1 and end 10/31. brThe monthly rate is $4000brbrWant to stay more than a week but less than a month brWe offer discounts. Please inquire.

Pet Friendly Paradise Close To Sarasota-Venice

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(4)

$263.93

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!

4-bedroom heated pool house 5 minutes to the beach

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(2)

$257.53

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 the highway if you need it. Plenty of room for your boat, RV, camper and vehicles. The large yard has beautiful trees and an 8 foot vinyl privacy fence all the way around to keep pets and family happy. We have everything you need to leave your worries behind and have a great stay.

4-bedroom heated Pool house in lovely Osprey, 5 minutes to the beach

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(10)

$290.08

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.brbrThe heart of the home is the kitchen, a modern haven for culinary inspiration. Fully stocked with premium appliances, cookware, and everything you need—from your morning coffee ritual to a gourmet dinner—preparing meals becomes a delight.brbrEmbrace the sun, sand, and surf! The cottage comes equipped with beach chairs, towels, and all the essentials for a perfect day by the water. Just grab your gear and let the beach adventures begin.brbrWe’ve anticipated every detail to make your stay effortless and enjoyable. From luxurious toiletries and plush towels to all the everyday essentials, every convenience is at your fingertips. Whether you’re here for a quick getaway or an extended retreat, comfort and ease are always part of the experience.

Cottage

Cozy Cottage in south Sarasota Florida, Close to Beaches!

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(3)

$216.72

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.brbrThis particular unit has 595 sqft and was completely remodeled in 2013 and has a loft-like, architecturally designed, open concept space. brIt comfortably sleeps max 2 adults (king size bed) and a max of 2 children (full size bed). brMaximum number of guests 4 persons, this number may not be exceeded even with a baby. brIt 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, a big walk-in shower, a toilet, and separately a washing machine, as well as a dryer. The bedroom also features a small desk to place your laptop and access the free WLAN. Sited perfectly is a small patio facing the lake. brCommon area amenities include a pool and pool house specifically for Windsor Lodge residents and guests, and an expansive lobby available for private functions.brbrThe Oaks is a private club. The club facilities are NOT accessible for the Windsor Lodge guests (Golf, Tennis, Fitness, Restaurants, Community Pools). The pool at the Windsor Lodge is solely for the Windsor Lodge guests though.

Windsor Lodge Unit 7, studio, close to the beaches, pool access

Osprey, Florida, United States

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Bath

Sleeps

$233.91

Experience very private, exclusive Osprey like a local in this 3-bedroom condo. brbrThe 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. brbrTake 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, SUP - or just enjoy the views off your balcony for the flying fish and manatees. A quick drive to Nokomis Beach and Venice, but not that far from Siesta Key or Sarasota if you have the urge. brbrLuxury amenities include: heated swimming pool, two hot tubs, outdoor shower, kayak launch, picnic area, gas grils, gym, sauna, and a private clubhouse with a pool table. brbrShopping for everything you need is around the corner, but away from Rt 41 traffic and noise. Not a peep!. The condo stays comfortable year-round with heating and air conditioning. Whether you’re unwinding after a day of exploring or catching up on work, this wonderful condo provides a peaceful retreat. brbrWe're happy to assist with any questions while you stay at our condo. 2 parking spaces, covered and secured. The price includes all fees, nothing hidden.brbrHOA APPROVAL REQUIRED – MESSAGE HOST BEFORE REQUESTING TO BOOKbrbrComplex association requires renter application and background check allow 20 days for this prior to your arrival date.

Condo

Spacious 3-BR + large den condo in private, quiet luxury Casey Key area

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(3)

$209.7

Luxurious apartment with fabulous lake view at the Windsor Lodge. Large living-/bedroom with kitchenette, sep. bath, community pool, sleeps 4.brbrOn 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 people (maximum 2 Adults+2Kids). Maximum number of guests 4 persons, this number may not be exceeded even with a baby.brThe WLAN for our guests is for free. A small seating area in the backyard offers a beautiful view of the lake. On the first floor, we provide a washer and dryer for our guests. The first floor is accessible with an elevator.brbrThe Oaks is a private club. The club facilities are NOT accessible for the Windsor Lodge guests (Golf, Tennis, Fitness, Restaurants, Community Pools). The pool at the Windsor Lodge is solely for the Windsor Lodge guests though.

Windsor Lodge Unit 3, studio, close to the beaches, pool access

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(4)

$224.99

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.brbrOn 595 sqft living space with stunning lake- and golf course views, an open space living area with King Size Bed awaits you. brThe kitchen is fully equipped: Fridge, Stove, dishes, glasses. The TV provides entertainment for everyone. brThe air-conditioning is installed with the highest standards. brYou also have access to free WLAN. A washer and a dryer is in the Windsor Lodge Building.brMaximum Occupancy 2 Adults+ 2 Kids. Maximum number of guests 4 persons, this number may not be exceeded even with a baby.brbrThe Oaks is a private club. The club facilities are NOT accessible for the Windsor Lodge guests (Golf, Tennis, Fitness, Restaurants, Community Pools). The pool at the Windsor Lodge is solely for the Windsor Lodge guests though.

Windsor Lodge Unit 18, studio, close to the beaches, pool access

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(5)

$224.99

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.brbrOn 595 sqft living space a living-, eating and sleeping area with kitchenette awaits you. brThe bathroom has a sink, a walk-in shower and a toilet. brThe kitchenette is equipped with a microwave, a fridge, 2 stove burners and a coffeemaker. brDishes, glasses and cutlery are provided for 4 people. brAir Condition, WiFi and TV are provided. brThe king size bed together with the queen size inflatable sleeping mattress are offering space for 4 people (maximum 2 Adults+2Kids). brMaximum number of guests 4 persons, this number may not be exceeded even with a baby.brOn the same floor, we provide a washer and dryer for our guests. brThe second floor is accessible with an elevator.brbrThe Oaks is a private club. The club facilities are NOT accessible for the Windsor Lodge guests (Golf, Tennis, Fitness, Restaurants, Community Pools). brThe pool at the Windsor Lodge is solely for the Windsor Lodge guests though.brbrThe Windsor Lodge with 20 Apartments is located within the prestigious The Oaks Golf and Country Club, in Osprey, only a few minutes away from the islands Casey Key and Siesta Key with their beautiful beaches. Restaurants (Mad Moes, Max's Table, Rosebuds, Roessler's) and grocery stores (Publix, Sprouts, Walmart) are all within the range of 4 miles.

Windsor Lodge Unit 15, studio, close to the beaches, pool access

Osprey, Florida, United States

Bed

Bath

Sleeps

$241.59

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.brbrLight and bright, furnished apartment with a wonderful view of the adjoining lake and the golf course from your private balcony. brOn 623 sqft living space a separate bedroom with king size bed, living - dining room, kitchenette with stove, oven, microwave, toaster, dishwasher, fridge, freezer, coffee machine. brThe bathroom has a big walk-in shower, a toilet, a sink and a washing machine and dryer. There are 1 TV and highspeed internet. brThe unit accommodates 2 adults and 2 children. Maximum number of guests 4 persons, this number may not be exceeded even with a baby.brYou can enjoy the Pool of the Windsor Lodge.brbrThe Oaks is a private club. The club facilities are NOT accessible for the Windsor Lodge guests (Golf, Tennis, Fitness, Restaurants, Community Pools). The pool at the Windsor Lodge is solely for the Windsor Lodge guests though.

Windsor Lodge Unit 20, studio, 1BR/1BA, close to beaches, balcony, pool access

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(1)

$209.7

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.brThe unit features an open and inviting layout with a comfortable living area that flows seamlessly into the sleeping space, creating a bright and relaxed atmosphere. A separate bathroom provides convenience and privacy. The living area is perfect for unwinding after a day spent at the beach, exploring Sarasota, or enjoying the amenities of The Oaks community.brGuests staying at Windsor Lodge have access to the community pool, offering a refreshing place to relax and enjoy Florida’s warm climate. The quiet, well-kept surroundings of The Oaks are known for their lush landscaping and tranquil ambiance.brUnit 19 is conveniently located close to beaches, shopping, restaurants, and Sarasota-area attractions, making it an excellent choice for both short stays and longer visits. Whether you’re looking to relax, enjoy the golf course views, or explore the Gulf Coast, Unit 19 at Windsor Lodge provides a comfortable and elegant home base in one of the area’s most desirable communities.

Windsor Lodge Unit #19, studio close to beaches

Osprey, Florida, United States

Bed

Bath

Sleeps

$221.17

Windsor Lodge at The Oaks Golf and Country Club: Luxurious, high quality furnished golf course rental with community pool.brEnjoy a wonderful view of the adjoining lake and the golf course from your patio. brOn 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. br2 TVs and free internet. The unit accommodates 2 adults. Maximum number of guests 2 persons, this number may not be exceeded even with a baby or a child.brbrThe Oaks is a private club. The club facilities are NOT accessible for the Windsor Lodge guests (Golf, Tennis, Fitness, Restaurants, Community Pools). The pool at the Windsor Lodge is solely for the Windsor Lodge guests though.

Windsor Lodge Unit 5, studio, close to the beaches, pool access

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(28)

$262.59

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. There’s a second living room with a large glass door to the pool deck as well as a separate luxury dining area. The villa is air-conditioned with central controls. It is surrounded by a large scale yard with beautiful old tropical as well as citrus fruit trees. The large screened pool area is located in the back of the L-shaped villa. The seating area on the pool deck is partly roofed and overlooks the generously sized heated pool as well as a beautiful waterfall.brbrKeywords: house, near beaches, pool, jaccuzi, spa

Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(4)

$217.99

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.brbrCompletely furnished studio with a wonderful view of the adjoining lake and the golf course behind it. brOn 680 sqft living space a living-, eating and sleeping area awaits you. brThe bathroom has 2 separate sinks, a walk-in shower, a toilet and a washing machine and dryer. brThe kitchenette includes dishwasher and refrigerator as well as granite countertops, two burner stove, microwave and Keurig coffeemaker. brThe Smart TV provides entertainment for everyone. brThe Full Size has a TempurPedic mattress and the sleeping sofa offers space for additional 2 people. brMaximum Occupancy 2 Adults+2 Kids.brMaximum number of guests 4 persons, this number may not be exceeded even with a baby.brbrThe Oaks is a private club. The club facilities are NOT accessible for the Windsor Lodge guests (Golf, Tennis, Fitness, Restaurants, Community Pools). The pool at the Windsor Lodge is solely for the Windsor Lodge guests though.

Windsor Lodge Unit 10, Studio, close to the beaches, pool access

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(2)

$136.57

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, brbrYour vacation retreat at 751 Pine Run in Osprey, FL, offers a charming, laid-back experience with easy access to both nature and modern conveniences. Nestled in a wooded area off Blackburn Point Rd, this quiet coastal village is an escape from the crowded coastline, with no busy downtown but plenty to explore nearby.brJust a short walk brings you to outdoor malls with landscaped sidewalks, fountains, and a mix of local shops, including a grocery store, pharmacy, and several restaurants. Venturing toward the Gulf, you'll experience a classic Florida vibe with parks, fishing piers, a boardwalk, and the newly opened Blue Lagoon restaurant, where you can catch dolphins playing in the water and breathtaking sunsets.brCross the historic turn-style bridge over the Intracoastal Waterway to reach Casey Key Tiki Bar and Restaurant. Here, you’ll find water taxis, jet ski rentals, kayak rentals, and fishing excursions—everything you need for a day on the water. Beyond another small bridge is Casey Key Road, a scenic route lined with beautiful homes, including that of famed author Stephen King, who drew inspiration for his novel Duma Key from this very area. Further down Casey Road you will reach the public beachesbrFor more nature-filled activities, head a mile south on Highway 41 to Oscar Scherer State Park. This park offers scenic kayaking, a swimming lake, hiking trails, camping, and regular events, including a Thursday morning blueberry pancake breakfast. Whether you're looking for quiet relaxation or coastal adventure, your retreat in Osprey gives you the best of both worlds.brbrbrWe look forward to welcoming you to our place.brbr* Consecutive Monthly (4 weeks) Discount *: a 10% discount will be applied to each additional consecutive month after the first month.. to be appied at signing and included with deposit refund.

Condo

Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(2)

$255.46

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 traffic of the bigger cities.br This place feels like home away from home.brThe king bedroom has an attached bathroom with a shower. There is a queen bedroom that is also attached to a full bath. The third bedroom has a full over full bunk bed as well as a twin bed. We also have a gaming console for entertaining the kids. We have a well stocked kitchen with the tools you need to make dinner, smoothies, panini's, and more so you can make yourself right at home as well as a grill outdoors for your use.

5 minutes to the BEACH! Beautiful neighborhood on intercoastal. Family friendly

Osprey, Florida, United States

Bed

Bath

Sleeps

$286.21

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 in charming Venice and Sarasota. Book now and enjoy everything this superb house has to offer.

Cozy home, pet friendly, private pool & close to beach. Minimum 60 days

Osprey, Florida, United States

Bed

Bath

Sleeps

$143.51

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 gorgeous sunset over the gulf. Kayak and paddle board rentals nearby. Walk to restaurants. 2 pools to enjoy. Gas grilling area with fire pit for use. Non smoking relaxed atmosphere. Quiet community with mature trees and nature trails.

Condo

Enjoy this Condo Hideaway Casey Key area of Sarasota Relax and Enjoy this Secret

Osprey, Florida, United States

Bed

Bath

Sleeps

Exceptional(36)

$142.22