Holiday rentals near The Oaks Club
We found 5,872 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals close to The Oaks Club that provide the perfect home base for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include air conditioning and a pool. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - The Oaks Club
Showing deals for:19 Dec - 26 Dec
Image gallery for Modern near Siesta Beach
9.89.8 out of 10 rating
Exceptional
(45 reviews)
Modern near Siesta Beach
Sarasota, FL
8% off
Price is NZ$6,674
NZ$6,674
for 7 nights, 1 home
NZ$953 per night
includes taxes & fees
Image gallery for Bright Spacious Cottage Near Downtown, Restaurants, Shopping & Beaches
1010 out of 10 rating
Exceptional
(5 reviews)
Bright Spacious Cottage Near Downtown, Restaurants, Shopping & Beaches
Sarasota, FL
8% off
Price is NZ$4,996
NZ$4,996
for 7 nights, 1 home
NZ$714 per night
includes taxes & fees
Image gallery for Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
Sarasota, FL
7% off
Price is NZ$7,204
NZ$7,204
for 7 nights, 1 home
NZ$1,029 per night
includes taxes & fees
Image gallery for Hyde Park Villa w/ Saltwater Pool + Fire Place!
9.09.0 out of 10 rating
Wonderful
(14 reviews)
Hyde Park Villa w/ Saltwater Pool + Fire Place!
Sarasota, FL
7% off
Price is NZ$7,102
NZ$7,102
for 7 nights, 1 home
NZ$1,015 per night
includes taxes & fees
Image gallery for Sandy Feet Retreat | Private Pool + Ping Pong!
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Sandy Feet Retreat | Private Pool + Ping Pong!
Sarasota, FL
7% off
Price is NZ$9,279
NZ$9,279
for 7 nights, 1 home
NZ$1,326 per night
includes taxes & fees
Image gallery for Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
1010 out of 10 rating
Exceptional
(41 reviews)
Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
Sarasota, FL
8% off
Price is NZ$5,142
NZ$5,142
for 7 nights, 1 home
NZ$735 per night
includes taxes & fees
Image gallery for Sunshine Haven | HUGE Backyard, Private heated Pool + Fire Pit!
1010 out of 10 rating
Exceptional
(12 reviews)
Sunshine Haven | HUGE Backyard, Private heated Pool + Fire Pit!
Sarasota, FL
7% off
Price is NZ$6,390
NZ$6,390
for 7 nights, 1 home
NZ$913 per night
includes taxes & fees
Image gallery for Beachfront Paradise with Private Beach Access, Pools, Tennis, Cabana Rentals & More at Palm Bay Club
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Beachfront Paradise with Private Beach Access, Pools, Tennis, Cabana Rentals & More at Palm Bay Club
Siesta Key, FL
7% off
Price is NZ$7,134
NZ$7,134
for 7 nights, 1 apartment
NZ$1,019 per night
includes taxes & fees
Image gallery for Renovated Jamaica Royale Condo: Private Beach Access, Modern Comforts, and Steps to the Pool!
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Renovated Jamaica Royale Condo: Private Beach Access, Modern Comforts, and Steps to the Pool!
Siesta Key, FL
8% off
Price is NZ$5,859
NZ$5,859
for 7 nights, 1 apartment
NZ$837 per night
includes taxes & fees
Image gallery for Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
9.69.6 out of 10 rating
Exceptional
(22 reviews)
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Siesta Key, FL
8% off
Price is NZ$5,819
NZ$5,819
for 7 nights, 1 home
NZ$831 per night
includes taxes & fees
Image gallery for Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
1010 out of 10 rating
Exceptional
(34 reviews)
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Sarasota, FL
7% off
Price is NZ$4,968
NZ$4,968
for 7 nights, 1 home
NZ$710 per night
includes taxes & fees
Image gallery for Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
9.29.2 out of 10 rating
Wonderful
(25 reviews)
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Sarasota, FL
8% off
Price is NZ$3,232
NZ$3,232
for 7 nights, 1 home
NZ$462 per night
includes taxes & fees
Image gallery for Tropical Backyard Oasis! Prime Location Near Main St & Trolley to Lido Beach!
1010 out of 10 rating
Exceptional
(121 reviews)
Tropical Backyard Oasis! Prime Location Near Main St & Trolley to Lido Beach!
Sarasota, FL
8% off
Price is NZ$3,308
NZ$3,308
for 7 nights, 1 home
NZ$473 per night
includes taxes & fees
Image gallery for Lido Key Villa! Walk to Beach, St. Armand's Circle, Heated Pool, & Perfect Location!
9.09.0 out of 10 rating
Wonderful
(45 reviews)
Lido Key Villa! Walk to Beach, St. Armand's Circle, Heated Pool, & Perfect Location!
Sarasota, FL
6% off
Price is NZ$4,324
NZ$4,324
for 7 nights, 1 apartment
NZ$618 per night
includes taxes & fees
Image gallery for Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!
Siesta Key, FL
5% off
Price is NZ$4,250
NZ$4,250
for 7 nights, 1 apartment
NZ$607 per night
includes taxes & fees
Image gallery for Cozy, Upscale, Modern Studio, Walk to Lido Beach, Heated Pool, $185 Free Activities Daily
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Cozy, Upscale, Modern Studio, Walk to Lido Beach, Heated Pool, $185 Free Activities Daily
Sarasota, FL
9% off
Price is NZ$4,144
NZ$4,144
for 7 nights, 1 apartment
NZ$592 per night
includes taxes & fees
Image gallery for 2 Cottages Rented Together | Amazing Heated Pool | Near Beaches
1010 out of 10 rating
Exceptional
(58 reviews)
2 Cottages Rented Together | Amazing Heated Pool | Near Beaches
Sarasota, FL
8% off
Price is NZ$8,673
NZ$8,673
for 7 nights, 1 home
NZ$1,239 per night
includes taxes & fees
Image gallery for Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
9.49.4 out of 10 rating
Exceptional
(64 reviews)
Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
Sarasota, FL
7% off
Price is NZ$3,166
NZ$3,166
for 7 nights, 1 home
NZ$452 per night
includes taxes & fees
Image gallery for Newly Updated Jamaica Royale Villa: Private Beach, Pools, & Free Daily Activities!
9.69.6 out of 10 rating
Exceptional
(79 reviews)
Newly Updated Jamaica Royale Villa: Private Beach, Pools, & Free Daily Activities!
Siesta Key, FL
7% off
Price is NZ$7,614
NZ$7,614
for 7 nights, 1 apartment
NZ$1,088 per night
includes taxes & fees
Image gallery for Unbeatable Ocean Views from Multiple Rooms and Balcony, Private Beach | Free Excursion
9.49.4 out of 10 rating
Exceptional
(48 reviews)
Unbeatable Ocean Views from Multiple Rooms and Balcony, Private Beach | Free Excursion
Siesta Key, FL
6% off
Price is NZ$16,452
NZ$16,452
for 7 nights, 1 apartment
NZ$2,350 per night
includes taxes & fees
Image gallery for Spacious 5th-Floor Condo with Floor-to-Ceiling Views | Steps to Siesta Key Beach | Pool & Amenities!
9.09.0 out of 10 rating
Wonderful
(46 reviews)
Spacious 5th-Floor Condo with Floor-to-Ceiling Views | Steps to Siesta Key Beach | Pool & Amenities!
Siesta Key, FL
9% off
Price is NZ$7,232
NZ$7,232
for 7 nights, 1 apartment
NZ$1,033 per night
includes taxes & fees
Image gallery for Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
1010 out of 10 rating
Exceptional
(239 reviews)
Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
Siesta Key, FL
8% off
Price is NZ$4,099
NZ$4,099
for 7 nights, 1 apartment
NZ$586 per night
includes taxes & fees
Image gallery for Pool home in Sarasota, Florida. Short drive to Siesta Key beach
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Pool home in Sarasota, Florida. Short drive to Siesta Key beach
Sarasota, FL
7% off
Price is NZ$3,047
NZ$3,047
for 7 nights, 1 home
NZ$435 per night
includes taxes & fees
Image gallery for Lower Pricing! Palm Bay Private Beach, 2 Heated Pools | Hot Tub | Bay Sunrises, Ready to Book!
9.29.2 out of 10 rating
Wonderful
(99 reviews)
Lower Pricing! Palm Bay Private Beach, 2 Heated Pools | Hot Tub | Bay Sunrises, Ready to Book!
Siesta Key, FL
7% off
Price is NZ$7,136
NZ$7,136
for 7 nights, 1 apartment
NZ$1,019 per night
includes taxes & fees
Find spaces that suit your style
Find the best place to stay - The Oaks Club
Windsor Lodge Unit 3, studio, close to the beaches, pool access
Sleeps 4 · 1 bedroom · 1 bathroom
8.88.8 out of 10
Excellentexcellent
3 reviews(3 reviews)
Pool House Overlooking Lake on Skye Ranch
Sleeps 6 · 3 bedrooms · 3 bathrooms
SIESTA KEY #1 BEACH:4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE
Sleeps 28 · 8 bedrooms · 8 bathrooms
9.89.8 out of 10
Exceptionalexceptional
118 reviews(118 reviews)
2-bedroom Spacious townhome in Osprey
Sleeps 5 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Windsor Lodge Unit 15, studio, close to the beaches, pool access
Sleeps 2 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Homey Comfort Meets Championship Golf–Ground Floor Condo in Stoneybrook Sarasota
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value