Vacation Rentals with Private Pool in Islamorada, FL: Compare 10+ Sites & Save

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98 Best Vacation Rentals with Private Pool in Islamorada (Starting from $316)

Cozy Islamorada retreat!
Cozy Islamorada retreat!
House
Islamorada, FL, 33036, United States
0.1k from Islamorada center

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

4 Bedrooms8 Guests
New to Booking
$461
Average price / night
Check Availability
Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!
Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!
House
Islamorada, FL, 33036, United States
0.2k from Islamorada center

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

2 Bedrooms3 Guests
New to Booking
$318
Average price / night
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Charming 3BR retreat in Islamorada, perfect for family getaways!
Charming 3BR retreat in Islamorada, perfect for family getaways!
House
Islamorada, FL, 33036, United States
0.2k from Islamorada center

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

3 Bedrooms6 Guests
New to Booking
$567
Average price / night
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Spacious 4BR home in Islamorada with a heated pool, perfect for family getaways!
Spacious 4BR home in Islamorada with a heated pool, perfect for family getaways!
House
Islamorada, FL, 33036, United States
0.3k from Islamorada center

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

4 Bedrooms8 Guests
New to Booking
$515
Average price / night
Check Availability
Experience comfort at Mini Ray's of Sunshine in Islamorada, perfect for families!
Experience comfort at Mini Ray's of Sunshine in Islamorada, perfect for families!
House
Islamorada, FL, 33036, United States
0.3k from Islamorada center

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

4 Bedrooms10 Guests
New to Booking
$517
Average price / night
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Islamorada Beach Beachfront, Fire Pit & Pool
Islamorada Beach Beachfront, Fire Pit & Pool
House
Islamorada, FL, 33036, United States
0.4k from Islamorada center

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

6 Bedrooms12 Guests
8.0

Good

1 reviews

$2804
Average price / night
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Beautiful Pool home in Islamorada
Beautiful Pool home in Islamorada
House
Islamorada, FL, 33036, United States
0.4k from Islamorada center

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

3 Bedrooms6 Guests
New to Booking
$316
Average price / night
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Discover One Too Mini, a cozy 3-bedroom getaway in Islamorada, perfect for 8!
Discover One Too Mini, a cozy 3-bedroom getaway in Islamorada, perfect for 8!
House
Islamorada, FL, 33036, United States
0.5k from Islamorada center

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

3 Bedrooms8 Guests
New to Booking
$497
Average price / night
Check Availability
Southern Diversion Estate  Islamorada
Southern Diversion Estate Islamorada
House
Islamorada, FL, 33036, United States
0.6k from Islamorada center

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

5 Bedrooms16 Guests
9.8

Exceptional

84 reviews

$2096
Average price / night
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Discover Sea Ranch in Islamorada: spacious 4BR home with private pool and stunning views.
Discover Sea Ranch in Islamorada: spacious 4BR home with private pool and stunning views.
House
Islamorada, FL, 33036, United States
0.7k from Islamorada center

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

4 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1600
Average price / night
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Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
House
Islamorada, FL, 33036, United States
0.8k from Islamorada center

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

9 Bedrooms18 Guests
New to Booking
$2378
Average price / night
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Discover 'The Oasis': a stunning 3-bedroom retreat in Islamorada with a heated private pool.
Discover 'The Oasis': a stunning 3-bedroom retreat in Islamorada with a heated private pool.
House
Islamorada, FL, 33036, United States
0.8k from Islamorada center

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

3 Bedrooms8 Guests
8.0

Good

1 reviews

$2145
Average price / night
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Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests.
Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests.
House
Islamorada, FL, 33036, United States
0.9k from Islamorada center

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

5 Bedrooms10 Guests
New to Booking
$1516
Average price / night
Check Availability
Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
House
Islamorada, FL, 33036, United States
1.1k from Islamorada center

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

5 Bedrooms10 Guests
10.0

Exceptional

84 reviews

$1494
Average price / night
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3‑Acre Oceanfront Estate w/ Pool ON the Atlantic, 2 Homes & Beach
3‑Acre Oceanfront Estate w/ Pool ON the Atlantic, 2 Homes & Beach
House
Islamorada, FL, 33036, United States
1.1k from Islamorada center

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

3 Bedrooms8 Guests
10.0

Exceptional

49 reviews

$1409
Average price / night
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Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More!
Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More!
House
Islamorada, FL, 33036, United States
1.2k from Islamorada center

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

8 Bedrooms22 Guests
New to Booking
$3309
Average price / night
Check Availability
10 Bedroom Private Ocean Front Estate
10 Bedroom Private Ocean Front Estate
Villa
Islamorada, FL, 33036, United States
1.4k from Islamorada center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

10 Bedrooms22 Guests
10.0

Exceptional

1 reviews

$3453
Average price / night
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Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.7k from Islamorada center

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

3 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$645
Average price / night
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Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.
Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.
House
Islamorada, FL, 33036, United States
1.7k from Islamorada center

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

5 Bedrooms10 Guests
10.0

Exceptional

72 reviews

$1453
Average price / night
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Isla Key Acaí: Waterfront Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Isla Key Acaí: Waterfront Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.8k from Islamorada center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$673
Average price / night
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Islamorada Happy Tarpon House: Heated Pool - Deep Water  Boat Dock- Family Fun!
Islamorada Happy Tarpon House: Heated Pool - Deep Water Boat Dock- Family Fun!
House
Islamorada, FL, 33036, United States
1.8k from Islamorada center

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

3 Bedrooms6 Guests
10.0

Exceptional

62 reviews

$873
Average price / night
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5 bedroom - Deep Dockage & Heated Pool in Islamorada.
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
House
Islamorada, FL, 33036, United States
1.9k from Islamorada center

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

5 Bedrooms10 Guests
10.0

Exceptional

124 reviews

$1350
Average price / night
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Spacious 5BR home in Islamorada, perfect for 14 guests with ocean views.
Spacious 5BR home in Islamorada, perfect for 14 guests with ocean views.
House
Islamorada, FL, 33036, United States
2.0k from Islamorada center

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

5 Bedrooms14 Guests
9.2

Superb

12 reviews

$1283
Average price / night
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Waterfront, boat dock, private oasis in the heart of Islamorada! Pool & Sunsets!
Waterfront, boat dock, private oasis in the heart of Islamorada! Pool & Sunsets!
House
Islamorada, FL, 33036, United States
2.2k from Islamorada center

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

4 Bedrooms7 Guests
10.0

Exceptional

5 reviews

$1566
Average price / night
Check Availability
Experience luxury at Heart of Morada, a 3-bedroom condo in beautiful Islamorada.
Experience luxury at Heart of Morada, a 3-bedroom condo in beautiful Islamorada.
House
Islamorada, FL, 33036, United States
2.2k from Islamorada center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$1114
Average price / night
Check Availability
Seaside Sanctuary in the Heart of Islamorada
Seaside Sanctuary in the Heart of Islamorada
House
Islamorada, FL, 33036, United States
2.3k from Islamorada center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$1163
Average price / night
Check Availability
Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Villa
Islamorada, FL, 33036, United States
2.3k from Islamorada center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$654
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 Islamorada.

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Islamorada Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 98 verified vacation rentals with a private pool in Islamorada. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Islamorada vary depending on the property size, location, and travel season. Rates typically start from around $316 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 Islamorada also welcome pets. Currently, 19 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 Islamorada often include additional features such as Kitchen, Laundry, and Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Islamorada 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.