Vacation Rentals in The Oaks Club, FL: Compare 10+ Sites & Save

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  4.  Florida
  5.  Sarasota
  6.  The Oaks Club

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2032 Best Vacation Rentals in The Oaks Club (Starting from $139)

Windsor Lodge Unit 20, studio, 1BR 1BA close to the beaches, pool access
Windsor Lodge Unit 20, studio, 1BR 1BA close to the beaches, pool access
Apartment
Osprey, FL, USA
0.7k from The Oaks Club center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$176
Average price / night
Check Availability
Windsor Lodge Unit 3, studio, close to the beaches, pool access
Windsor Lodge Unit 3, studio, close to the beaches, pool access
Apartment
Osprey, FL, 34229, United States
0.4k from The Oaks Club center

AC, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
8.8

Fabulous

3 reviews

$209
Average price / night
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Windsor Lodge Unit 3 close to the Beaches Siesta Key
Windsor Lodge Unit 3 close to the Beaches Siesta Key
Apartment
Osprey, FL, USA
0.7k from The Oaks Club center

Apartments, Accommodations, Pools, Parking, Cabins, Lodgings, Places to stay, Family, Self-catering

1 Bedroom4 Guests
9.0

Fabulous

1 reviews

$206
Average price / night
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Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
House
Osprey, FL, 34229, United States
0.4k from The Oaks Club center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

5 reviews

$248
Average price / night
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Windsor Lodge Unit #19, studio close to beaches
Windsor Lodge Unit #19, studio close to beaches
Apartment
Osprey, FL, USA
0.7k from The Oaks Club center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$223
Average price / night
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Cozy Cottage in south Sarasota Florida, Close to Beaches!
Cozy Cottage in south Sarasota Florida, Close to Beaches!
Cottage
Osprey, FL, 34229, United States
0.5k from The Oaks Club center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

3 Bedrooms6 Guests
9.8

Exceptional

9 reviews

$275
Average price / night
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Bay Acres Bungalow - A
Bay Acres Bungalow - A
Apartment
Osprey, FL, USA
1.0k from The Oaks Club center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay, Bungalows

2 Bedrooms6 Guests
New to Booking
$323
Average price / night
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Windsor Lodge Unit 20, studio, 1BR/1BA, close to beaches, balcony, pool access
Windsor Lodge Unit 20, studio, 1BR/1BA, close to beaches, balcony, pool access
Apartment
Osprey, FL, 34229, United States
0.5k from The Oaks Club center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
New to Booking
$241
Average price / night
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Bay Acres Bungalow
Bay Acres Bungalow
House
Osprey, FL, USA
1.0k from The Oaks Club center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Bungalows

2 Bedrooms12 Guests
New to Booking
$543
Average price / night
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Newly Renovated Tranquil 3-Bdrm Home in Osprey- Close to Beaches Dogs Okay
Newly Renovated Tranquil 3-Bdrm Home in Osprey- Close to Beaches Dogs Okay
House
Osprey, FL, 34229, United States
0.5k from The Oaks Club center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$189
Average price / night
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Bay Acres Bungalow - B
Bay Acres Bungalow - B
House
Osprey, FL, USA
1.1k from The Oaks Club center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Bungalows

2 Bedrooms6 Guests
New to Booking
$288
Average price / night
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Cozy beach bungalow
Cozy beach bungalow
House
Osprey, FL, 34229, United States
0.6k from The Oaks Club center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$218
Average price / night
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King Bed & Patio, Minutes to the Beach
King Bed & Patio, Minutes to the Beach
House
Osprey, FL, USA
1.1k from The Oaks Club center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
7.3

Good

3 reviews

$278
Average price / night
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Windsor Lodge Unit 10, Studio, close to the beaches, pool access
Windsor Lodge Unit 10, Studio, close to the beaches, pool access
Apartment
Osprey, FL, 34229, United States
0.7k from The Oaks Club center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

1 Bedroom4 Guests
10.0

Exceptional

4 reviews

$218
Average price / night
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Modern luxe getaway for families near Siesta Key
Modern luxe getaway for families near Siesta Key
House
Osprey, FL, USA
1.3k from The Oaks Club center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
8.5

Very Good

2 reviews

$317
Average price / night
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Windsor Lodge Unit 15, studio, close to the beaches, pool access
Windsor Lodge Unit 15, studio, close to the beaches, pool access
Apartment
Osprey, FL, 34229, United States
0.7k from The Oaks Club center

AC, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
9.2

Superb

5 reviews

$222
Average price / night
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Pool, Hot tub, Close to Beaches, Shopping, More!
Pool, Hot tub, Close to Beaches, Shopping, More!
House
The Oaks Club, Osprey, Florida, USA
1.3k from The Oaks Club center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Jacuzzis

3 Bedrooms8 Guests
New to Booking
$425
Average price / night
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Cute 3/2 Siesta home steps from Siesta waters
Cute 3/2 Siesta home steps from Siesta waters
House
Sarasota, FL, USA
2.7k from The Oaks Club center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$252
Average price / night
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Charming Osprey Home
Charming Osprey Home
House
Osprey, FL, 34229, United States
0.7k from The Oaks Club center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$414
Average price / night
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5 Mi to Beach Family Retreat in Sarasota!
5 Mi to Beach Family Retreat in Sarasota!
House
Sarasota, FL, USA
2.8k from The Oaks Club center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$177
Average price / night
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Fall is the best time! To vacation here,\nAvail ALL Autumn till NYE 2025!
Fall is the best time! To vacation here,\nAvail ALL Autumn till NYE 2025!
House
Osprey, FL, 34229, United States
0.7k from The Oaks Club center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
New to Booking
$139
Average price / night
Check Availability
Windsor Lodge Unit 7, studio, close to the beaches, pool access
Windsor Lodge Unit 7, studio, close to the beaches, pool access
Apartment
Osprey, FL, 34229, United States
0.9k from The Oaks Club center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Pool, Washer

1 Bedroom4 Guests
9.4

Superb

3 reviews

$216
Average price / night
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Warm & Cozy Family Home in a Quiet Neighborhood
Warm & Cozy Family Home in a Quiet Neighborhood
House
Osprey, FL, 34229, United States
0.9k from The Oaks Club center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms10 Guests
New to Booking
$320
Average price / night
Check Availability
Sunny Coastal Escape
Sunny Coastal Escape
House
Osprey, FL, 34229, United States
1.0k from The Oaks Club center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$418
Average price / night
Check Availability
Windsor Lodge Unit 5, studio, close to the beaches, pool access
Windsor Lodge Unit 5, studio, close to the beaches, pool access
Apartment
Osprey, FL, 34229, United States
1.1k from The Oaks Club center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

1 Bedroom2 Guests
New to Booking
$217
Average price / night
Check Availability
Windsor Lodge Unit 18, studio, close to the beaches, pool access
Windsor Lodge Unit 18, studio, close to the beaches, pool access
Apartment
Osprey, FL, 34229, United States
1.1k from The Oaks Club center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

1 Bedroom4 Guests
9.6

Exceptional

4 reviews

$222
Average price / night
Check Availability
Sarasota Vacation paradise!
Sarasota Vacation paradise!
House
Osprey, FL, 34229, United States
1.1k from The Oaks Club center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, Washer

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$324
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in The Oaks Club.

Where to stay in The Oaks Club? Best neighborhoods & areas

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Frequently Asked Questions

You can explore 2032 verified vacation rentals in The Oaks Club. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in The Oaks Club vary depending on the season, property size, and location. Rates typically start from around $139 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in The Oaks Club include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in The Oaks Club welcome pets. Currently, 38 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in The Oaks Club often include amenities such as Fireplace/Heating, Laundry, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.