Vacation Rentals with Pool in Holiday Harbor, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Pensacola
  6.  Holiday Harbor

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2222 Best Vacation Rentals with Pool in Holiday Harbor (Starting from $116)

Perdido Escape Spacious 3BR 3BA Condo Beach Pool
Perdido Escape Spacious 3BR 3BA Condo Beach Pool
Apartment
FL, USA
0.4k from Holiday Harbor center

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

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$400
Average price / night
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\"Lucky View\" | Private Pool | Boat Dock | Waterfront | Beach Getaways
\"Lucky View\" | Private Pool | Boat Dock | Waterfront | Beach Getaways
House
Pensacola, FL, 32507, United States
0.3k from Holiday Harbor center

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

3 Bedrooms15 Guests
9.0

Fabulous

4 reviews

$1420
Average price / night
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Sailmakers place 206
Sailmakers place 206
House
FL, USA
0.4k from Holiday Harbor center

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

3 Bedrooms6 Guests
New to Booking
$310
Average price / night
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Gulf Coast Beach Daze, at Lost Key Golf & Beach Club \n3-BR 2-BA Condo
Gulf Coast Beach Daze, at Lost Key Golf & Beach Club \n3-BR 2-BA Condo
Condo
Pensacola, FL, 32507, United States
0.4k from Holiday Harbor center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$347
Average price / night
Check Availability
Lost Key 403A
Lost Key 403A
Apartment
Perdido Key, FL, USA
0.4k from Holiday Harbor center

Apartments, Accommodations, Pools, 4-star, Lodgings, Hot tubs, Places to stay

3 Bedrooms8 Guests
New to Booking
$116
Average price / night
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Golf. BEACH. Pool. REPEAT! Experience the Lost Key Lifestyle! Free Golf!!
Golf. BEACH. Pool. REPEAT! Experience the Lost Key Lifestyle! Free Golf!!
Condo
Pensacola, FL, 32507, United States
0.4k from Holiday Harbor center

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

2 Bedrooms7 Guests
10.0

Exceptional

4 reviews

$266
Average price / night
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Santo Amaro 801B - Lost Key Golf & Beach
Santo Amaro 801B - Lost Key Golf & Beach
Apartment
Holiday Harbor, Pensacola, Florida, USA
0.4k from Holiday Harbor center

Apartments, Accommodations, Pools, Lodgings, Hot tubs, Places to stay, Accessible hotels

3 Bedrooms7 Guests
New to Booking
$292
Average price / night
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Sunset-View Resort Condo on Perdido Key
Sunset-View Resort Condo on Perdido Key
Condo
Pensacola, FL, 32507, United States
0.4k from Holiday Harbor center

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

2 Bedrooms6 Guests
New to Booking
$212
Average price / night
Check Availability
Lost Key 14338 Beach Heather Ct By Pkrm
Lost Key 14338 Beach Heather Ct By Pkrm
Apartment
Pensacola, FL, USA
0.4k from Holiday Harbor center

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

2 Bedrooms8 Guests
New to Booking
$278
Average price / night
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Eighth floor condo with pools and hot tub, WiFi, central AC, & Bluetooth system
Eighth floor condo with pools and hot tub, WiFi, central AC, & Bluetooth system
Condo
Perdido Key, FL, 32507, United States
0.4k from Holiday Harbor center

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

3 Bedrooms7 Guests
New to Booking
$332
Average price / night
Check Availability
Santo Amaro #705B at Lost Key
Santo Amaro #705B at Lost Key
Apartment
Perdido Key, FL, USA
0.4k from Holiday Harbor center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Hot tubs, Places to stay

3 Bedrooms8 Guests
New to Booking
$319
Average price / night
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Resort Condo w/ Screened Porch & Shared Pools, Hot Tubs, Beach Club, Golf, Gym
Resort Condo w/ Screened Porch & Shared Pools, Hot Tubs, Beach Club, Golf, Gym
Condo
Perdido Key, FL, 32507, United States
0.4k from Holiday Harbor center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Hot Tub, Kitchen, Microwave

3 Bedrooms8 Guests
New to Booking
$345
Average price / night
Check Availability
La Salbadora #402C at Lost Key
La Salbadora #402C at Lost Key
Apartment
Perdido Key, FL, USA
0.4k from Holiday Harbor center

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

2 Bedrooms6 Guests
New to Booking
$270
Average price / night
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Perdido House - Your Home Away with Private Pool and Dock
Perdido House - Your Home Away with Private Pool and Dock
House
Pensacola, FL, 32507, United States
0.4k from Holiday Harbor center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms12 Guests
9.8

Exceptional

126 reviews

$546
Average price / night
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14070 Canal Drive By Pkrm
14070 Canal Drive By Pkrm
House
Pensacola, FL, USA
0.4k from Holiday Harbor center

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

3 Bedrooms12 Guests
New to Booking
$644
Average price / night
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Coastal Elegance: Beautiful Townhome Embodies The Lost Key Lifestyle!
Coastal Elegance: Beautiful Townhome Embodies The Lost Key Lifestyle!
Condo
Pensacola, FL, 32507, United States
0.4k from Holiday Harbor center

AC, Balcony, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms12 Guests
9.8

Exceptional

22 reviews

$362
Average price / night
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Lost Key B702
Lost Key B702
House
Perdido Key, FL, USA
0.4k from Holiday Harbor center

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

2 Bedrooms6 Guests
New to Booking
$206
Average price / night
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Family Fun Awaits: The Sweet & Salty Coastal-Casual Haven with Inviting Pool!
Family Fun Awaits: The Sweet & Salty Coastal-Casual Haven with Inviting Pool!
House
Pensacola, FL, 32507, United States
0.4k from Holiday Harbor center

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

3 Bedrooms12 Guests
10.0

Exceptional

22 reviews

$437
Average price / night
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Lost Key B304
Lost Key B304
House
Perdido Key, FL, USA
0.4k from Holiday Harbor center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$212
Average price / night
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Find your way to Lost Key! Enjoy Free Golf & A VIP Beach Club On The Gulf!
Find your way to Lost Key! Enjoy Free Golf & A VIP Beach Club On The Gulf!
Condo
Perdido Key, FL, 32507, United States
0.4k from Holiday Harbor center

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

3 Bedrooms6 Guests
9.0

Fabulous

10 reviews

$310
Average price / night
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9 Min to Private Beach + POOL + Beautiful Home!
9 Min to Private Beach + POOL + Beautiful Home!
House
Pensacola, FL, 32507, United States
0.5k from Holiday Harbor center

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

4 Bedrooms13 Guests
New to Booking
$773
Average price / night
Check Availability
🌴Beach Club Access + Shuttle | Onsite Golf Course ⛳ Lost Key 201C
🌴Beach Club Access + Shuttle | Onsite Golf Course ⛳ Lost Key 201C
Condo
Perdido Key, FL, 32507, United States
0.5k from Holiday Harbor center

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

4 Bedrooms8 Guests
New to Booking
$402
Average price / night
Check Availability
Resort Condo w/ Screened Porch & Shared Pools, Hot Tubs, Gym, Beach Club, Golf
Resort Condo w/ Screened Porch & Shared Pools, Hot Tubs, Gym, Beach Club, Golf
Condo
Perdido Key, FL, 32507, United States
0.5k from Holiday Harbor center

AC, Barbecue, Dryer, Elevator, Heater, Hot Tub, Kitchen, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$389
Average price / night
Check Availability
Golf getaway near the beach with shared pool, balcony, & WiFi - gorgeous view
Golf getaway near the beach with shared pool, balcony, & WiFi - gorgeous view
Condo
Perdido Key, FL, 32507, United States
0.5k from Holiday Harbor center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Heater, Internet, Kitchen

2 Bedrooms6 Guests
New to Booking
$230
Average price / night
Check Availability
The Stay 'N' Play Condo! Free Golf! Private Beach Club!
The Stay 'N' Play Condo! Free Golf! Private Beach Club!
Condo
Perdido Key, FL, 32507, United States
0.5k from Holiday Harbor center

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

3 Bedrooms8 Guests
8.4

Very Good

5 reviews

$226
Average price / night
Check Availability
Right On Lost Key Golf Course With Beach Club Privileges! Free Golf too!
Right On Lost Key Golf Course With Beach Club Privileges! Free Golf too!
Condo
Perdido Key, FL, 32507, United States
0.5k from Holiday Harbor center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Heater, Hot Tub

2 Bedrooms6 Guests
8.0

Good

1 reviews

$278
Average price / night
Check Availability
Lost Key Penthouse! Unit 1001A In Perdido Key, FL With Gorgeous Panoramic Views!
Lost Key Penthouse! Unit 1001A In Perdido Key, FL With Gorgeous Panoramic Views!
Condo
Pensacola, FL, 32507, United States
0.6k from Holiday Harbor center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$383
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 Pool in Holiday Harbor.

Stay Near Holiday Harbor's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Holiday Harbor Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 2222 verified vacation rentals with a pool in Holiday Harbor. 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 Holiday Harbor vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $116 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Holiday Harbor 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 Holiday Harbor welcome pets. Currently, 21 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 Holiday Harbor often include additional outdoor features such as Pool, Fireplace/Heating, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Holiday Harbor 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.