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

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378 Best Vacation Rentals with Pool in Islamorada (Starting from $252)

Beacon Reef 222
Beacon Reef 222
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$252
Average price / night
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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
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Chesapeake Beach Resort
Chesapeake Beach Resort
Resort
Islamorada, FL, USA
0.5k from Islamorada center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

45 Bedrooms75 Guests
8.0

Good

846 reviews

$536
Average price / night
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BOOK YOUR DREAM VACATION at  BEACON REEF - SPECIAL MAY DEAL
BOOK YOUR DREAM VACATION at BEACON REEF - SPECIAL MAY DEAL
Condo
Islamorada, FL, 33036, United States
0.2k from Islamorada center

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

2 Bedrooms4 Guests
9.4

Superb

9 reviews

$321
Average price / night
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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Resort
Islamorada, FL, USA
1.4k from Islamorada center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

26 Bedrooms69 Guests
8.4

Very Good

26 reviews

$649
Average price / night
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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
Check Availability
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
1.5k from Islamorada center

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

3 Bedrooms6 Guests
New to Booking
$802
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
Check Availability
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
1.5k from Islamorada center

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

3 Bedrooms6 Guests
New to Booking
$737
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
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Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Villa
Islamorada, FL, USA
1.5k from Islamorada center

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

3 Bedrooms6 Guests
New to Booking
$627
Average price / night
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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
Check Availability
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
1.5k from Islamorada center

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

3 Bedrooms6 Guests
New to Booking
$617
Average price / night
Check Availability
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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Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
House
Islamorada, FL, USA
1.5k from Islamorada center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$966
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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Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
House
Islamorada, FL, USA
1.5k from Islamorada center

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

3 Bedrooms6 Guests
New to Booking
$1186
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
Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Villa
Islamorada, FL, USA
1.5k from Islamorada center

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

3 Bedrooms6 Guests
New to Booking
$1281
Average price / night
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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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Islander Resort
Islander Resort
Resort
Islamorada, FL, USA
2.0k from Islamorada center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Beach

107 Bedrooms68 Guests
8.7

Fabulous

1451 reviews

$348
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
Check Availability
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
Check Availability
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
Check Availability
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
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 Islamorada.

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Islamorada Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 378 verified vacation rentals with a pool in Islamorada. 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 Islamorada vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $252 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Islamorada 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 Islamorada welcome pets. Currently, 24 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 Islamorada often include additional outdoor features such as Pool, Internet, and Wellness Facilities. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Islamorada 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.