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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Islamorada
  6.  Hurricane Monument

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326 Best Vacation Rentals with Pool in Hurricane Monument (Starting from $248)

Bayside Villas by Islander Resort
Bayside Villas by Islander Resort
Resort
Islamorada, FL, USA
0.3k from Hurricane Monument center

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

20 Bedrooms30 Guests
8.6

Fabulous

232 reviews

$345
Average price / night
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Beautiful Home located in Downtown Islamorada
Beautiful Home located in Downtown Islamorada
House
Islamorada, FL, 33036, United States
0.3k from Hurricane Monument center

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

2 Bedrooms5 Guests
New to Booking
$248
Average price / night
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Cheeca Lodge & Spa
Cheeca Lodge & Spa
Resort
Islamorada, FL, USA
0.5k from Hurricane Monument center

Luxury, Accommodations, Pools, Resorts, Parking, Spa, Golf, Romantic, 5-star

243 Bedrooms64 Guests
8.7

Fabulous

977 reviews

$865
Average price / night
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One Ten Palms ~ Charming Islamorada Beachfront Home with Heated Pool
One Ten Palms ~ Charming Islamorada Beachfront Home with Heated Pool
House
Islamorada, FL, 33036, United States
0.4k from Hurricane Monument center

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

3 Bedrooms10 Guests
New to Booking
$1482
Average price / night
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Islander Resort
Islander Resort
Resort
Islamorada, FL, USA
1.1k from Hurricane Monument 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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Beautiful bayfront house, private pool and dock, right in Downtown Islamorada
Beautiful bayfront house, private pool and dock, right in Downtown Islamorada
House
Islamorada, FL, 33036, United States
0.4k from Hurricane Monument center

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

3 Bedrooms6 Guests
9.8

Exceptional

12 reviews

$1430
Average price / night
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Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
1.6k from Hurricane Monument 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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Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
1.6k from Hurricane Monument 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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4-Bedroom Oceanfront Home in the Heart of Islamorada
4-Bedroom Oceanfront Home in the Heart of Islamorada
House
Islamorada, FL, 33036, United States
0.8k from Hurricane Monument center

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

4 Bedrooms8 Guests
New to Booking
$1041
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
1.6k from Hurricane Monument 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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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
0.8k from Hurricane Monument center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$654
Average price / night
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Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
1.6k from Hurricane Monument center

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

3 Bedrooms6 Guests
New to Booking
$617
Average price / night
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Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Villa
Islamorada, FL, 33036, United States
0.8k from Hurricane Monument center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$683
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
1.6k from Hurricane Monument 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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Just relisted! Discounts on longer stays ~ Heart of Islamorada ~ Boat Dockage
Just relisted! Discounts on longer stays ~ Heart of Islamorada ~ Boat Dockage
House
Islamorada, FL, 33036, United States
0.8k from Hurricane Monument center

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

4 Bedrooms8 Guests
10.0

Exceptional

50 reviews

$1040
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
1.6k from Hurricane Monument 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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New Islamorada Home w/Dock, 2 Pools, Kayaks & EV Charger
New Islamorada Home w/Dock, 2 Pools, Kayaks & EV Charger
House
Islamorada, FL, 33036, United States
0.8k from Hurricane Monument center

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

3 Bedrooms6 Guests
10.0

Exceptional

33 reviews

$995
Average price / night
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Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Villa
Islamorada, FL, USA
1.6k from Hurricane Monument 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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Islamorada Florida Bay Villa  Plunge Pool, Boat Dock, Amazing Sunset Views
Islamorada Florida Bay Villa Plunge Pool, Boat Dock, Amazing Sunset Views
Villa
Islamorada, FL, 33036, United States
0.8k from Hurricane Monument center

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

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$1074
Average price / night
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Pines & Palms Resort
Pines & Palms Resort
Resort
Hurricane Monument, Islamorada, Florida, USA
1.6k from Hurricane Monument center

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

24 Bedrooms44 Guests
9.0

Fabulous

762 reviews

$282
Average price / night
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Seaside Sanctuary in the Heart of Islamorada
Seaside Sanctuary in the Heart of Islamorada
House
Islamorada, FL, 33036, United States
0.9k from Hurricane Monument center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$1163
Average price / night
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Book Now! Discounted Pricing Last Minute Availability
Book Now! Discounted Pricing Last Minute Availability
House
Islamorada, FL, 33036, United States
0.9k from Hurricane Monument center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$1156
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
0.9k from Hurricane Monument center

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

4 Bedrooms7 Guests
10.0

Exceptional

5 reviews

$1566
Average price / night
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Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Villa
Islamorada, FL, 33036, United States
0.9k from Hurricane Monument center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$979
Average price / night
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Coral Cove Resort - ‘A Fisherman’s Dream’
Coral Cove Resort - ‘A Fisherman’s Dream’
House
Islamorada, FL, 33036, United States
0.9k from Hurricane Monument center

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

3 Bedrooms6 Guests
9.8

Exceptional

27 reviews

$287
Average price / night
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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
1.0k from Hurricane Monument center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$1114
Average price / night
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Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
Condo
Islamorada, FL, 33036, United States
1.1k from Hurricane Monument center

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

3 Bedrooms6 Guests
10.0

Exceptional

74 reviews

$662
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 Hurricane Monument.

Where to stay in Hurricane Monument? Best neighborhoods & areas

Hurricane Monument Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 326 verified vacation rentals with a pool in Hurricane Monument. 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 Hurricane Monument vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $248 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Hurricane Monument 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 Hurricane Monument welcome pets. Currently, 25 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 Hurricane Monument often include additional outdoor features such as Pool, Wellness Facilities, and Internet. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Hurricane Monument 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.