Vacation Rentals with Pool in Harbor Island, CA: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  California

  5.  San Diego
  6.  Harbor Island

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421 Best Vacation Rentals with Pool in Harbor Island (Starting from $165)

DoubleTree by Hilton San Diego Bayside
DoubleTree by Hilton San Diego Bayside
Resort
San Diego, CA, USA
2.1k from Harbor Island center

Accommodations, Pools, Resorts, Parking, Romantic, 3-star, Lodgings, Hot tubs, Places to stay

291 Bedrooms56 Guests
7.8

Good

415 reviews

$272
Average price / night
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\"1 to 16 Guests - Main House + Guest House & Pool\"
\"1 to 16 Guests - Main House + Guest House & Pool\"
House
San Diego, CA, 92106, United States
2.5k from Harbor Island center

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

6 Bedrooms16 Guests
10.0

Exceptional

2 reviews

$1647
Average price / night
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Stunning Views, Rooftop Vista, Pool & Spa
Stunning Views, Rooftop Vista, Pool & Spa
Villa
San Diego, CA, USA
2.6k from Harbor Island center

Pool, Air Conditioner, Security/Safety, Hot Tub, View, Pet Friendly, Barbecue/Outdoor Cooking

1 Bedroom12 Guests
New to Booking
$855
Average price / night
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Luxury 5BD/4BA Mission Hills/Stunning Rooftop + Skyline Views
Luxury 5BD/4BA Mission Hills/Stunning Rooftop + Skyline Views
House
San Diego, CA, 92110, United States
2.6k from Harbor Island center

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

5 Bedrooms14 Guests
9.4

Superb

216 reviews

$1225
Average price / night
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Downtown San Diego Condo with Pool and Rooftop Access
Downtown San Diego Condo with Pool and Rooftop Access
Apartment
San Diego, CA, USA
2.8k from Harbor Island center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Hot tubs, Places to stay, Condos

1 Bedroom2 Guests
New to Booking
$169
Average price / night
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Enjoy Casa De Glory! City & Ocean Views  by NOVIQ
Enjoy Casa De Glory! City & Ocean Views by NOVIQ
House
San Diego, CA, 92103, United States
2.8k from Harbor Island center

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

6 Bedrooms13 Guests
8.0

Good

5 reviews

$1604
Average price / night
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Sunset Views Spa Pool Game Room BBQ Firepit
Sunset Views Spa Pool Game Room BBQ Firepit
House
San Diego, CA, USA
2.8k from Harbor Island center

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

1 Bedroom8 Guests
New to Booking
$1092
Average price / night
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Private Luxury Resort Home in ♥ of the City - Pool ♥ Spa ♥ Outdoor Lounge ♥ Casa Paradiso
Private Luxury Resort Home in ♥ of the City - Pool ♥ Spa ♥ Outdoor Lounge ♥ Casa Paradiso
House
San Diego, CA, 92103, United States
2.8k from Harbor Island center

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

4 Bedrooms10 Guests
10.0

Exceptional

159 reviews

$1615
Average price / night
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“Backyard Is OMG” Spa Pool BBQ Game Room Views
“Backyard Is OMG” Spa Pool BBQ Game Room Views
House
San Diego, CA, USA
2.8k from Harbor Island center

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

1 Bedroom10 Guests
New to Booking
$1766
Average price / night
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OMG!! A BLUE LAGOON IN THE ♥ OF THE CITY? POOL, GAME ROOM, VIEWS, LUXURY
OMG!! A BLUE LAGOON IN THE ♥ OF THE CITY? POOL, GAME ROOM, VIEWS, LUXURY
House
San Diego, CA, 92103, United States
2.8k from Harbor Island center

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

4 Bedrooms8 Guests
10.0

Exceptional

82 reviews

$1440
Average price / night
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Epic Resort Villa: Pool Spa Firepit View Games
Epic Resort Villa: Pool Spa Firepit View Games
House
Harbor Island, San Diego, California, USA
2.8k from Harbor Island center

Sports/Activities, Fireplace/Heating, Accessibility, Internet, Hot Tub, Guest Services, Pool

1 Bedroom10 Guests
New to Booking
$804
Average price / night
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BLUE LAGOON➕ BONUS APT ♦ GAMES ♦ POOL ♦ VIEWS ♦ LUXURY  - THIS PLACE IS NUTS!
BLUE LAGOON➕ BONUS APT ♦ GAMES ♦ POOL ♦ VIEWS ♦ LUXURY - THIS PLACE IS NUTS!
House
San Diego, CA, 92103, United States
2.8k from Harbor Island center

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

5 Bedrooms10 Guests
10.0

Exceptional

17 reviews

$1799
Average price / night
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Luxury Pool Haven Scenic Views and Summer Fireworks
Luxury Pool Haven Scenic Views and Summer Fireworks
Villa
San Diego, CA, USA
2.9k from Harbor Island center

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

5 Bedrooms14 Guests
New to Booking
$1349
Average price / night
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Urban Hi-Tech 2 BR Escape in Little Italy~Near Bay, Gas Lamp & Beaches!
Urban Hi-Tech 2 BR Escape in Little Italy~Near Bay, Gas Lamp & Beaches!
Condo
San Diego, CA, 92101, United States
2.8k from Harbor Island center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$191
Average price / night
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Luxury Point Loma Retreat Pool Spa Views
Luxury Point Loma Retreat Pool Spa Views
House
San Diego, CA, USA
3.0k from Harbor Island center

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

1 Bedroom12 Guests
New to Booking
$1047
Average price / night
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Luxury 2-bedroom condo with ocean views in Little Italy.
Luxury 2-bedroom condo with ocean views in Little Italy.
Condo
San Diego, CA, 92101, United States
2.9k from Harbor Island center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater

2 Bedrooms4 Guests
New to Booking
$165
Average price / night
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The zinnia-Downtown SDiego Marina View Stay
The zinnia-Downtown SDiego Marina View Stay
Apartment
San Diego, CA, USA
3.1k from Harbor Island center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$431
Average price / night
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☀️26’ SunDeck w/Ocean VIEWS  SUNSETS! - Fast Wifi
☀️26’ SunDeck w/Ocean VIEWS SUNSETS! - Fast Wifi
House
San Diego, CA, 92103, United States
2.9k from Harbor Island center

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

2 Bedrooms6 Guests
9.8

Exceptional

76 reviews

$552
Average price / night
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Downtown San Diego Condo 1 Mi to Gaslamp Quarter
Downtown San Diego Condo 1 Mi to Gaslamp Quarter
Apartment
San Diego, CA, USA
3.3k from Harbor Island center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Hot tubs, Places to stay, Condos

2 Bedrooms4 Guests
New to Booking
$213
Average price / night
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Luxury 5BR Private Pool Home w/ Panoramic Ocean Bay & City Views – Sleeps 12+
Luxury 5BR Private Pool Home w/ Panoramic Ocean Bay & City Views – Sleeps 12+
House
San Diego, CA, 92106, United States
2.9k from Harbor Island center

Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
10.0

Exceptional

147 reviews

$1460
Average price / night
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The Pool Side Hideaway with Golf Cart
The Pool Side Hideaway with Golf Cart
Apartment
San Diego, CA, USA
3.3k from Harbor Island center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Beach, Hot tubs

4 Bedrooms10 Guests
9.4

Superb

16 reviews

$1256
Average price / night
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Open for Summer/Pool and Spa/A/C/Pool Table/Pet Friendly
Open for Summer/Pool and Spa/A/C/Pool Table/Pet Friendly
House
San Diego, CA, 92110, United States
3.0k from Harbor Island center

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

4 Bedrooms10 Guests
9.4

Superb

6 reviews

$1186
Average price / night
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Pt Loma Condo - Across from Pechanga Arena and Central to Beaches and Downtown
Pt Loma Condo - Across from Pechanga Arena and Central to Beaches and Downtown
Condo
San Diego, CA, 92110, United States
3.0k from Harbor Island center

Balcony, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
10.0

Exceptional

5 reviews

$231
Average price / night
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Modern Luxury Executive Condo In The Most Prestigious Tower In Little Italy!
Modern Luxury Executive Condo In The Most Prestigious Tower In Little Italy!
Condo
San Diego, CA, 92101, United States
3.0k from Harbor Island center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Hot Tub, Internet

1 Bedroom3 Guests
10.0

Exceptional

17 reviews

$180
Average price / night
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Luxury furnished 2B/2BA, stunning views, premier Little Italy boutique high rise
Luxury furnished 2B/2BA, stunning views, premier Little Italy boutique high rise
Condo
San Diego, CA, 92101, United States
3.0k from Harbor Island center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

2 Bedrooms2 Guests
10.0

Exceptional

15 reviews

$194
Average price / night
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Heart & Soul of San Diego in Old Town. Private w/heated pool & Jacuzzi NEAR ALL.
Heart & Soul of San Diego in Old Town. Private w/heated pool & Jacuzzi NEAR ALL.
House
San Diego, CA, 92110, United States
3.0k from Harbor Island center

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

5 Bedrooms14 Guests
10.0

Exceptional

22 reviews

$1202
Average price / night
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Heart & Soul of San Diego W/ heated pool NEAR ALL.
Heart & Soul of San Diego W/ heated pool NEAR ALL.
House
San Diego, CA, 92110, United States
3.0k from Harbor Island center

AC, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms8 Guests
9.0

Fabulous

6 reviews

$775
Average price / night
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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 Pool in Harbor Island.

Where to stay in Harbor Island? Best neighborhoods & areas

Harbor Island Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 421 verified vacation rentals with a pool in Harbor Island. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Harbor Island vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $165 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Harbor Island offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Harbor Island welcome pets. Currently, 42 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Harbor Island often include additional outdoor features such as Pool, Wellness Facilities, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Harbor Island offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.