Short-Term 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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3618 Best Short-Term 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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Furnished and meticulous!  Near Nokomis, Venice and Siesta Beaches.
Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
Condo
Osprey, FL, 34229, United States
0.6k from The Oaks Club center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$249
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 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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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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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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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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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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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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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
2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!
2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!
Condo
Osprey, FL, 34229, United States
1.0k from The Oaks Club center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$193
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

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 Short-Term Rentals in The Oaks Club.

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The Oaks Club Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 3618 verified short-term rentals in The Oaks Club, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in The Oaks Club vary depending on location, property size, and travel dates. Rates typically start from around $139 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in The Oaks Club include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in The Oaks Club, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in The Oaks Club often include amenities such as Fireplace/Heating, Laundry, and Wellness Facilities, providing a comfortable and convenient stay.

Short-term rentals in The Oaks Club are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.