Vacation Rentals with Private Pool in Island Gallery West, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
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  6.  Island Gallery West

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1896 Best Vacation Rentals with Private Pool in Island Gallery West (Starting from $324)

Beach Front 2 Bedroom B
Beach Front 2 Bedroom B
House
Holmes Beach, FL, USA
0.9k from Island Gallery West center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

2 Bedrooms6 Guests
New to Booking
$1034
Average price / night
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Villa La Esperanza-203 Holmes Beach
Villa La Esperanza-203 Holmes Beach
House
Holmes Beach, FL, 34217, United States
0.1k from Island Gallery West center

AC, Balcony, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$612
Average price / night
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Anna Maria's Finest
Anna Maria's Finest
House
Anna Maria, FL, USA
2.7k from Island Gallery West center

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

3 Bedrooms6 Guests
8.2

Very Good

23 reviews

$891
Average price / night
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Dolphin Resort | Private Pool, Spa, Tiki Bar, Game Room & 3 Min Walk to Beach
Dolphin Resort | Private Pool, Spa, Tiki Bar, Game Room & 3 Min Walk to Beach
House
Holmes Beach, FL, 34217, United States
0.1k from Island Gallery West center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$573
Average price / night
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AM I Dreaming by AMI Locals
AM I Dreaming by AMI Locals
House
Island Gallery West, Holmes Beach, Florida, USA
3.5k from Island Gallery West center

Parking, Internet, Kitchen, Pet Friendly, Pool, Private Pool, Wheelchair Accessible

3 Bedrooms6 Guests
New to Booking
$425
Average price / night
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Hidden Haven / Private Pool & Hot Tub
Hidden Haven / Private Pool & Hot Tub
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

4 Bedrooms8 Guests
New to Booking
$823
Average price / night
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Bay Dreamin! Walk to the Beach, Pier, & Pine Ave! Heated Pool!
Bay Dreamin! Walk to the Beach, Pier, & Pine Ave! Heated Pool!
House
Anna Maria, FL, USA
3.7k from Island Gallery West center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach

5 Bedrooms8 Guests
New to Booking
$920
Average price / night
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Surf View ~ Walk to Beach/Rooftop Deck/Pool
Surf View ~ Walk to Beach/Rooftop Deck/Pool
House
Holmes Beach, FL, 34217, United States
0.1k from Island Gallery West center

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

8 Bedrooms16 Guests
New to Booking
$2697
Average price / night
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Anna Maria Island Retreat
Anna Maria Island Retreat
Apartment
Anna Maria, FL, USA
4.0k from Island Gallery West center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals

1 Bedroom6 Guests
6.7

Good

3 reviews

$532
Average price / night
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Lovely 3 bedroom duplex on Anna Maria Island, Private pool, pet friendly!
Lovely 3 bedroom duplex on Anna Maria Island, Private pool, pet friendly!
House
Holmes Beach, FL, 34217, United States
0.1k from Island Gallery West center

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

3 Bedrooms6 Guests
9.8

Exceptional

66 reviews

$604
Average price / night
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Aqua Paradise by AMI Locals
Aqua Paradise by AMI Locals
House
Island Gallery West, Holmes Beach, Florida, USA
5.0k from Island Gallery West center

Parking, Pool, Private Pool, Internet, Child Friendly

7 Bedrooms18 Guests
9.0

Fabulous

2 reviews

$795
Average price / night
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Charming Ground Level Resort Style 3 units Condo  of a TRIPLEX- unit A
Charming Ground Level Resort Style 3 units Condo of a TRIPLEX- unit A
Cottage
Holmes Beach, FL, 34217, United States
0.1k from Island Gallery West center

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

2 Bedrooms6 Guests
10.0

Exceptional

27 reviews

$402
Average price / night
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102 6Th St S- Upstairs Home
102 6Th St S- Upstairs Home
House
Bradenton Beach, FL, USA
5.1k from Island Gallery West center

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

3 Bedrooms6 Guests
New to Booking
$324
Average price / night
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Summer House-8 bedroom, Rooftop, short walk to the beach, private pool/spa and w
Summer House-8 bedroom, Rooftop, short walk to the beach, private pool/spa and w
House
Holmes Beach, FL, 34217, United States
0.1k from Island Gallery West center

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

8 Bedrooms20 Guests
9.4

Superb

26 reviews

$2238
Average price / night
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75 Palms! Sleeps 23! Luxury 1 acre lot Pool and Spa, Putting Green & Game Room!
75 Palms! Sleeps 23! Luxury 1 acre lot Pool and Spa, Putting Green & Game Room!
House
Bradenton, FL, USA
7.9k from Island Gallery West center

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

10 Bedrooms23 Guests
New to Booking
$2086
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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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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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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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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Honu Hale: Enjoy your tropical getaway!
Honu Hale: Enjoy your tropical getaway!
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

3 Bedrooms6 Guests
New to Booking
$620
Average price / night
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Beach Haven~Waterslide! Pool/Spa
Beach Haven~Waterslide! Pool/Spa
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

New to Booking
$2655
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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Black Pearl! NEW! Block and half to Beach!
Black Pearl! NEW! Block and half to Beach!
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

AC, Balcony, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1816
Average price / night
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Malibu Beach ~ Waterslide/Rooftop Views/Walk to Beach
Malibu Beach ~ Waterslide/Rooftop Views/Walk to Beach
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

8 Bedrooms16 Guests
New to Booking
$2073
Average price / night
Check Availability
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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Enclosed pool/spa - Stillpoint by SeaBreeze Vacation
Enclosed pool/spa - Stillpoint by SeaBreeze Vacation
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area

4 Bedrooms6 Guests
New to Booking
$548
Average price / night
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Peace 'n Paradise · Pool & Spa · 300 Yds Gulf
Peace 'n Paradise · Pool & Spa · 300 Yds Gulf
House
Holmes Beach, FL, 34217, United States
0.2k from Island Gallery West center

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

2 Bedrooms6 Guests
9.8

Exceptional

69 reviews

$503
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 with Private Pool in Island Gallery West.

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

Island Gallery West Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 1896 verified vacation rentals with a private pool in Island Gallery West. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Island Gallery West vary depending on the property size, location, and travel season. Rates typically start from around $324 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Island Gallery West also welcome pets. Currently, 23 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Island Gallery West often include additional features such as Private Pool, Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Island Gallery West include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.