Family-Friendly 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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1013 Best Family Vacation Rentals in The Oaks Club (Starting from $85)

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
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Windsor Lodge Unit #19, studio close to beaches
Windsor Lodge Unit #19, studio close to beaches
Apartment
Osprey, FL, 34229, United States
0.7k from The Oaks Club center

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

1 Bedroom4 Guests
New to Booking
$209
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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Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock
Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock
House
Osprey, FL, 34229, United States
1.2k from The Oaks Club center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

12 reviews

$298
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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2-bedroom Spacious townhome in Osprey
2-bedroom Spacious townhome in Osprey
House
Osprey, FL, 34229, United States
1.3k from The Oaks Club center

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

2 Bedrooms5 Guests
10.0

Exceptional

17 reviews

$143
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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Villa in Osprey that sleeps the whole family
Villa in Osprey that sleeps the whole family
Apartment
Osprey, FL, 34229, United States
1.3k from The Oaks Club center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms5 Guests
9.8

Exceptional

36 reviews

$130
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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Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis
Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis
Condo
Osprey, FL, 34229, United States
2.1k from The Oaks Club center

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

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$136
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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☀Coastal Gem☀Heated pool & amazing location!☀
☀Coastal Gem☀Heated pool & amazing location!☀
House
Sarasota, FL, 34231, United States
2.4k from The Oaks Club center

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

2 Bedrooms6 Guests
9.8

Exceptional

8 reviews

$343
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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Idyllic Casey Key Beach House
Idyllic Casey Key Beach House
House
Osprey, FL, 34229, United States
2.5k from The Oaks Club center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.6

Exceptional

37 reviews

$685
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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 Sarasota home in the Heart of the Gulfs most beautiful beaches.
Sarasota home in the Heart of the Gulfs most beautiful beaches.
House
Sarasota, FL, 34231, United States
2.5k from The Oaks Club center

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

3 Bedrooms6 Guests
10.0

Exceptional

30 reviews

$238
Average price / night
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Sarasota - Dunmore 8730
Sarasota - Dunmore 8730
House
Sarasota, FL, USA
3.1k from The Oaks Club center

Guest Services, Security/Safety, Pool, Barbecue/Outdoor Cooking, Child Friendly

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$180
Average price / night
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Dune walkway to water! A perfect beach bungalow, built for relaxation
Dune walkway to water! A perfect beach bungalow, built for relaxation
House
Nokomis, FL, 34275, United States
2.8k from The Oaks Club center

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

3 Bedrooms6 Guests
9.8

Exceptional

56 reviews

$492
Average price / night
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Tropical Shores Retreat-10 Min to Siesta Key Beach
Tropical Shores Retreat-10 Min to Siesta Key Beach
House
Sarasota, FL, USA
3.3k from The Oaks Club center

Air Conditioner, Parking, Security/Safety, Pet Friendly, Child Friendly

3 Bedrooms9 Guests
New to Booking
$292
Average price / night
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Adorable Cottage On Casey Key
Adorable Cottage On Casey Key
House
Nokomis, FL, 34275, United States
2.8k from The Oaks Club center

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

3 Bedrooms8 Guests
9.8

Exceptional

11 reviews

$871
Average price / night
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Pinestone Condo On Palmer Ranch
Pinestone Condo On Palmer Ranch
House
Sarasota, FL, USA
3.3k from The Oaks Club center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay, Condos

2 Bedrooms4 Guests
New to Booking
$292
Average price / night
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Now available!!  Spacious Private home, near beaches and all!
Now available!! Spacious Private home, near beaches and all!
House
Sarasota, FL, 34231, United States
2.9k from The Oaks Club center

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

3 Bedrooms6 Guests
9.2

Superb

18 reviews

$417
Average price / night
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Osprey Coastal Retreat Near Siesta Key
Osprey Coastal Retreat Near Siesta Key
House
Osprey, FL, USA
3.4k from The Oaks Club center

View, Sports/Activities, Guest Services, Internet, Fireplace/Heating, Parking, Balcony/Terrace

3 Bedrooms8 Guests
New to Booking
$85
Average price / night
Check Availability
Sprawling Island Retreat with New Pool, Spa, and Private Gulf Beach Access!
Sprawling Island Retreat with New Pool, Spa, and Private Gulf Beach Access!
House
Nokomis, FL, 34275, United States
3.0k from The Oaks Club center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms6 Guests
9.8

Exceptional

16 reviews

$427
Average price / night
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5-Bedroom Sarasota Retreat with Heated Pool mins to Siesta Beach/NO CLEANING FEE
5-Bedroom Sarasota Retreat with Heated Pool mins to Siesta Beach/NO CLEANING FEE
House
Sarasota, FL, 34231, United States
3.1k from The Oaks Club center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

5 Bedrooms9 Guests
10.0

Exceptional

8 reviews

$553
Average price / night
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Villa Colleen 4 BR 4 BA, solar heated Pool near Siesta Key Beach
Villa Colleen 4 BR 4 BA, solar heated Pool near Siesta Key Beach
House
Sarasota, FL, 34231, United States
3.1k from The Oaks Club center

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

4 Bedrooms8 Guests
9.8

Exceptional

31 reviews

$332
Average price / night
Check Availability
Siesta Key Modern Retreat with Heated Pool & Spa
Siesta Key Modern Retreat with Heated Pool & Spa
House
Sarasota, FL, 34231, United States
3.2k from The Oaks Club center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$693
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 Family Vacation Rentals in The Oaks Club.

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

The Oaks Club Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1013 verified family-friendly vacation rentals in The Oaks Club. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in The Oaks Club vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $85 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in The Oaks Club offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in The Oaks Club are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in The Oaks Club often include amenities such as Child Friendly, Fireplace/Heating, and Laundry. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.