Family-Friendly Vacation Rentals in Island Gallery West, FL: Compare 10+ Sites & Save

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2238 Best Family Vacation Rentals in Island Gallery West (Starting from $150)

Luxury 2BD Oceanfront Condo plus Private Parking, 2 Minute Walk to the Beach!
Luxury 2BD Oceanfront Condo plus Private Parking, 2 Minute Walk to the Beach!
Apartment
Holmes Beach, FL, USA
0.1k from Island Gallery West center

Apartments, Luxury, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay

2 Bedrooms6 Guests
9.9

Exceptional

28 reviews

$317
Average price / night
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By the Sand cozy 3 story house Steps from the Sand of Holmes Beach.
By the Sand cozy 3 story house Steps from the Sand of Holmes Beach.
House
Holmes Beach, FL, 34217, United States
0.1k from Island Gallery West center

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

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$531
Average price / night
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Surf View (AMIL)
Surf View (AMIL)
House
Holmes Beach, FL, USA
0.1k from Island Gallery West center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$1416
Average price / night
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Island Townhouse - 200 Steps to the Beach
Island Townhouse - 200 Steps to the Beach
House
Holmes Beach, FL, 34217, United States
0.1k from Island Gallery West center

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

2 Bedrooms4 Guests
9.8

Exceptional

81 reviews

$273
Average price / night
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7 Doors Down villa
7 Doors Down villa
Villa
Holmes Beach, FL, USA
0.1k from Island Gallery West center

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

3 Bedrooms6 Guests
New to Booking
$301
Average price / night
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Beachy Blue by Beach Boutique Rentals
Beachy Blue by Beach Boutique Rentals
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

4 Bedrooms8 Guests
7.0

Good

2 reviews

$813
Average price / night
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1 Step Closer villa
1 Step Closer villa
House
Holmes Beach, FL, USA
0.1k from Island Gallery West center

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

2 Bedrooms6 Guests
New to Booking
$261
Average price / night
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Beautiful New Pool/Spa, Steps to Sand & Restaurants, Golf Cart Included
Beautiful New Pool/Spa, Steps to Sand & Restaurants, Golf Cart Included
Cottage
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

2 Bedrooms6 Guests
10.0

Exceptional

11 reviews

$758
Average price / night
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Seahorse Villa East home
Seahorse Villa East home
Villa
Holmes Beach, FL, USA
0.1k from Island Gallery West center

Air Conditioner, Internet, Kitchen, Pet Friendly, Child Friendly

1 Bedroom4 Guests
New to Booking
$150
Average price / night
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2 Min Walk to Beach, Bikes, Paddleboards, Heated Pool, Hot Tub, Fireplace
2 Min Walk to Beach, Bikes, Paddleboards, Heated Pool, Hot Tub, Fireplace
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Free Parking, Heater

4 Bedrooms8 Guests
New to Booking
$1937
Average price / night
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Peace 'n Paradise
Peace 'n Paradise
House
Holmes Beach, FL, USA
0.2k from Island Gallery West center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$348
Average price / night
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Enjoyable 6 Minute Walk to Beach and Heated Saltwater Pool for ONLY Your Family.
Enjoyable 6 Minute Walk to Beach and Heated Saltwater Pool for ONLY Your Family.
Condo
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$508
Average price / night
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Coral Escape
Coral Escape
House
Holmes Beach, FL, USA
0.2k from Island Gallery West center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

6 Bedrooms12 Guests
New to Booking
$954
Average price / night
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Luxury Villa · Heated Saltwater Pool & Spa · Steps to Beach
Luxury Villa · Heated Saltwater Pool & Spa · Steps to Beach
Villa
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

4 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$601
Average price / night
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Malibu Beach
Malibu Beach
House
Holmes Beach, FL, USA
0.2k from Island Gallery West center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

8 Bedrooms16 Guests
New to Booking
$1170
Average price / night
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MI Island Time · Pool · Murphy Bed · 3-5 Min
MI Island Time · Pool · Murphy Bed · 3-5 Min
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$623
Average price / night
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Sun Daze
Sun Daze
House
Holmes Beach, FL, USA
0.2k from Island Gallery West center

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

2 Bedrooms4 Guests
New to Booking
$360
Average price / night
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Direct Beachfront 2 BD Condo On Florida’s Beautiful Gulf Coast!
Direct Beachfront 2 BD Condo On Florida’s Beautiful Gulf Coast!
Condo
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

2 Bedrooms4 Guests
10.0

Exceptional

124 reviews

$523
Average price / night
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Ainsley Beach House
Ainsley Beach House
House
Holmes Beach, FL, USA
0.2k from Island Gallery West center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1344
Average price / night
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Serendipity
Serendipity
House
Holmes Beach, FL, USA
0.2k from Island Gallery West center

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

3 Bedrooms6 Guests
New to Booking
$521
Average price / night
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PRIVATE HOUSE and Pool on AMI.  Close to beach, shopping, restaurants, marina.
PRIVATE HOUSE and Pool on AMI. Close to beach, shopping, restaurants, marina.
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$726
Average price / night
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Private Pool - Carefree Cottage by SeaBreeze Vacation
Private Pool - Carefree Cottage by SeaBreeze Vacation
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

3 Bedrooms6 Guests
10.0

Exceptional

40 reviews

$773
Average price / night
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Captain's Quarters: 1 Block to Beach, Dog Friendly, Pool
Captain's Quarters: 1 Block to Beach, Dog Friendly, Pool
House
Holmes Beach, FL, 34217, United States
0.3k from Island Gallery West center

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

3 Bedrooms6 Guests
10.0

Exceptional

54 reviews

$325
Average price / night
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Anna Maria 2 Family Home w/ pool, beach/3 blocks.
Anna Maria 2 Family Home w/ pool, beach/3 blocks.
House
Holmes Beach, FL, 34217, United States
0.3k from Island Gallery West center

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

3 Bedrooms6 Guests
10.0

Exceptional

61 reviews

$409
Average price / night
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Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wifi, Steps to Beach
Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wifi, Steps to Beach
House
Holmes Beach, FL, 34217, United States
0.3k from Island Gallery West center

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

3 Bedrooms6 Guests
9.8

Exceptional

58 reviews

$549
Average price / night
Check Availability
Beachfront - Sun Plaza West 214 by SeaBreeze Vacation
Beachfront - Sun Plaza West 214 by SeaBreeze Vacation
Condo
Holmes Beach, FL, 34217, United States
0.3k from Island Gallery West center

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

2 Bedrooms5 Guests
9.4

Superb

18 reviews

$511
Average price / night
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Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life
Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life
House
Holmes Beach, FL, 34217, United States
0.3k from Island Gallery West center

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

2 Bedrooms6 Guests
9.6

Exceptional

39 reviews

$762
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 Island Gallery West.

Where to stay in Island Gallery West? Best neighborhoods & areas

Island Gallery West Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2238 verified family-friendly vacation rentals in Island Gallery West. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Island Gallery West vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $150 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Island Gallery West 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 Island Gallery West 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 Island Gallery West often include amenities such as Child Friendly, Fireplace/Heating, and Pool. 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.