Vacation Rentals in Islandside Golf Course at Longboat Key Club, FL: Compare 10+ Sites & Save

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2989 Best Vacation Rentals in Islandside Golf Course at Longboat Key Club (Starting from $207)

Exquisite Gulf-Front Residence in Longboat Key
Exquisite Gulf-Front Residence in Longboat Key
Apartment
Longboat Key, FL, USA
0.6k from Islandside Golf Course at Longboat Key Club center

Bar, Internet, Security/Safety, Parking, Ev Charge Station, View, Pool

2 Bedrooms8 Guests
New to Booking
$450
Average price / night
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Inn on the Beach 7304 by FVC
Inn on the Beach 7304 by FVC
Apartment
Longboat Key, FL, 34228, United States
0.3k from Islandside Golf Course at Longboat Key Club center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$395
Average price / night
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Anything Is Possible
Anything Is Possible
House
Sarasota, FL, USA
1.7k from Islandside Golf Course at Longboat Key Club center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
9.0

Fabulous

4 reviews

$553
Average price / night
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Luxurious Beachfront Jr. Suite by FVC
Luxurious Beachfront Jr. Suite by FVC
Apartment
Longboat Key, FL, 34228, United States
0.4k from Islandside Golf Course at Longboat Key Club center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom2 Guests
9.4

Superb

79 reviews

$466
Average price / night
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Luxe Oasis - 517
Luxe Oasis - 517
House
Sarasota, FL, USA
1.8k from Islandside Golf Course at Longboat Key Club center

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

4 Bedrooms8 Guests
New to Booking
$948
Average price / night
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Precise Realty presents The Limetree Oasis
Precise Realty presents The Limetree Oasis
House
Longboat Key, FL, 34228, United States
0.6k from Islandside Golf Course at Longboat Key Club center

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

4 Bedrooms8 Guests
New to Booking
$547
Average price / night
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You Only Live Once
You Only Live Once
House
Sarasota, FL, USA
1.8k from Islandside Golf Course at Longboat Key Club center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$340
Average price / night
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Chic Pet Friendly Lido Key Home w Pool Near Beach & Shops: Rondy Home by RVA
Chic Pet Friendly Lido Key Home w Pool Near Beach & Shops: Rondy Home by RVA
House
Sarasota, FL, 34236, United States
0.7k from Islandside Golf Course at Longboat Key Club center

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

4 Bedrooms8 Guests
8.8

Fabulous

3 reviews

$458
Average price / night
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King Bed - Walk to St. Armand's Circle and Lido Beach in Minutes!
King Bed - Walk to St. Armand's Circle and Lido Beach in Minutes!
Apartment
Sarasota, FL, USA
2.1k from Islandside Golf Course at Longboat Key Club center

Transportation/Shuttle, Laundry, Ocean View, Oceanfront, Wellness Facilities, Sports/Activities, Fireplace/Heating

1 Bedroom4 Guests
6.9

Good

15 reviews

$239
Average price / night
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Newly remodeled beach house by Lido Beach and private pool
Newly remodeled beach house by Lido Beach and private pool
House
Sarasota, FL, 34236, United States
0.7k from Islandside Golf Course at Longboat Key Club center

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

4 Bedrooms10 Guests
9.8

Exceptional

28 reviews

$1304
Average price / night
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The Ringling Estate
The Ringling Estate
House
Sarasota, FL, USA
2.1k from Islandside Golf Course at Longboat Key Club center

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

6 Bedrooms16 Guests
New to Booking
$3450
Average price / night
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Lido Key Getaway With Heated Private Pool and Private Beach Access
Lido Key Getaway With Heated Private Pool and Private Beach Access
House
Sarasota, FL, 34236, United States
0.8k from Islandside Golf Course at Longboat Key Club center

AC, Internet, Kitchen, No Smoking, Pool, TV

3 Bedrooms6 Guests
New to Booking
$269
Average price / night
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Luxury Longboat Key Condo - Walk to Beach Access!
Luxury Longboat Key Condo - Walk to Beach Access!
Apartment
Longboat Key, FL, USA
2.2k from Islandside Golf Course at Longboat Key Club center

Apartments, Luxury, Accommodations, Parking, Spa, Lodgings, Beach, Hot tubs, Places to stay

2 Bedrooms4 Guests
New to Booking
$379
Average price / night
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Precise Realty presents The Waterway Escape
Precise Realty presents The Waterway Escape
House
Longboat Key, FL, 34228, United States
0.8k from Islandside Golf Course at Longboat Key Club center

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

2 Bedrooms4 Guests
New to Booking
$495
Average price / night
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Five Palms - 354
Five Palms - 354
House
Bailey Hall, FL, USA
2.2k from Islandside Golf Course at Longboat Key Club center

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

5 Bedrooms10 Guests
New to Booking
$3556
Average price / night
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Lido Key Luxury Pool Home–Perfect for Families Lido Shores Sanctuary by RVA
Lido Key Luxury Pool Home–Perfect for Families Lido Shores Sanctuary by RVA
House
Sarasota, FL, 34236, United States
0.9k from Islandside Golf Course at Longboat Key Club center

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

4 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$672
Average price / night
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Dream Island
Dream Island
House
Sarasota, FL, USA
2.2k from Islandside Golf Course at Longboat Key Club center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

8 Bedrooms16 Guests
New to Booking
$1455
Average price / night
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Waterfront Coastal 3 BR/3 BTH w/ Pool, 50ft. Boat Dock, Walk to Beach
Waterfront Coastal 3 BR/3 BTH w/ Pool, 50ft. Boat Dock, Walk to Beach
House
Longboat Key, FL, 34228, United States
0.9k from Islandside Golf Course at Longboat Key Club center

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

3 Bedrooms8 Guests
10.0

Exceptional

39 reviews

$627
Average price / night
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The Shore House
The Shore House
House
Bailey Hall, FL, USA
2.2k from Islandside Golf Course at Longboat Key Club center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

7 Bedrooms19 Guests
10.0

Exceptional

1 reviews

$1811
Average price / night
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Country Club Shores 4brm pool home by FVC
Country Club Shores 4brm pool home by FVC
House
Longboat Key, FL, 34228, United States
1.0k from Islandside Golf Course at Longboat Key Club center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms7 Guests
New to Booking
$527
Average price / night
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John Ringling House
John Ringling House
House
Sarasota, FL, USA
2.2k from Islandside Golf Course at Longboat Key Club center

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

3 Bedrooms10 Guests
8.0

Good

2 reviews

$1428
Average price / night
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Tropical Canal Home–Pool, Sun & Water Access: Paradise Cottage in LBK by RVA
Tropical Canal Home–Pool, Sun & Water Access: Paradise Cottage in LBK by RVA
House
Longboat Key, FL, 34228, United States
1.0k from Islandside Golf Course at Longboat Key Club center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$308
Average price / night
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Villa Sereno Summary:
Villa Sereno Summary:
House
Longboat Key, FL, 34228, United States
1.2k from Islandside Golf Course at Longboat Key Club center

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

5 Bedrooms10 Guests
New to Booking
$885
Average price / night
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Beach and Boaters Paradise! Heated pool, Fish off the dock, walk to the beach!
Beach and Boaters Paradise! Heated pool, Fish off the dock, walk to the beach!
House
Longboat Key, FL, 34228, United States
1.4k from Islandside Golf Course at Longboat Key Club center

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

4 Bedrooms8 Guests
10.0

Exceptional

37 reviews

$433
Average price / night
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3 bedroom pool home by FVC
3 bedroom pool home by FVC
House
Sarasota, FL, 34236, United States
1.5k from Islandside Golf Course at Longboat Key Club center

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

3 Bedrooms8 Guests
7.0

Good

2 reviews

$1276
Average price / night
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Tranquil Waterfront home- Water, peace, sunshine, & sand, this is your place. \n
Tranquil Waterfront home- Water, peace, sunshine, & sand, this is your place. \n
House
Longboat Key, FL, 34228, United States
1.7k from Islandside Golf Course at Longboat Key Club center

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

3 Bedrooms6 Guests
New to Booking
$232
Average price / night
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Charming Longboat Key 3-bedroom house with 3 min walk to beach
Charming Longboat Key 3-bedroom house with 3 min walk to beach
House
Longboat Key, FL, 34228, United States
1.7k from Islandside Golf Course at Longboat Key Club center

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

3 Bedrooms6 Guests
New to Booking
$207
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 Islandside Golf Course at Longboat Key Club.

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Frequently Asked Questions

You can explore 2989 verified vacation rentals in Islandside Golf Course at Longboat Key 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 Islandside Golf Course at Longboat Key Club vary depending on the season, property size, and location. Rates typically start from around $207 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 Islandside Golf Course at Longboat Key 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 Islandside Golf Course at Longboat Key Club welcome pets. Currently, 48 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 Islandside Golf Course at Longboat Key Club often include amenities such as Pool, Wellness Facilities, and Fireplace/Heating. 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.