Vacation Rentals with Pool in Theater of the Sea, FL: Compare 10+ Sites & Save

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  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Islamorada
  6.  Theater of the Sea

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418 Best Vacation Rentals with Pool in Theater of the Sea (Starting from $222)

Oceanfront Islamorada Townhome with Dock and Pool
Oceanfront Islamorada Townhome with Dock and Pool
House
Islamorada, FL, USA
0.2k from Theater of the Sea center

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

3 Bedrooms7 Guests
New to Booking
$764
Average price / night
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NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
House
Islamorada, FL, 33036, United States
0.1k from Theater of the Sea center

AC, Arcade, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$756
Average price / night
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Drop Anchor Resort & Marina
Drop Anchor Resort & Marina
Resort
Islamorada, FL, USA
0.5k from Theater of the Sea center

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

18 Bedrooms43 Guests
7.7

Good

341 reviews

$377
Average price / night
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Oceanfront Panoramic Bliss • 3 Stories, Paddleboards, Gameroom & Boat Dockage
Oceanfront Panoramic Bliss • 3 Stories, Paddleboards, Gameroom & Boat Dockage
House
Islamorada, FL, 33036, United States
0.2k from Theater of the Sea center

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

3 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$817
Average price / night
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Anglers Reef Vacation Rental
Anglers Reef Vacation Rental
Villa
Islamorada, FL, USA
0.7k from Theater of the Sea center

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

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$495
Average price / night
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Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-Friendly
Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-Friendly
House
Islamorada, FL, 33036, United States
0.2k from Theater of the Sea center

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

3 Bedrooms7 Guests
10.0

Exceptional

5 reviews

$757
Average price / night
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Anglers Reef Paradise
Anglers Reef Paradise
House
Islamorada, FL, USA
0.7k from Theater of the Sea center

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

2 Bedrooms6 Guests
9.6

Exceptional

19 reviews

$400
Average price / night
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At The Sandbar: Partial Ocean View, Htd Pool, Free Dockage, GameRoom, EV Charger
At The Sandbar: Partial Ocean View, Htd Pool, Free Dockage, GameRoom, EV Charger
House
Islamorada, FL, 33036, United States
0.3k from Theater of the Sea center

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

3 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$628
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
0.8k from Theater of the Sea 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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Oceanfront Paradise w/ Speakeasy, Karaoke, Pool & Dock for Endless Play
Oceanfront Paradise w/ Speakeasy, Karaoke, Pool & Dock for Endless Play
House
Islamorada, FL, 33036, United States
0.3k from Theater of the Sea center

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

3 Bedrooms8 Guests
New to Booking
$766
Average price / night
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Chesapeake Beach Resort
Chesapeake Beach Resort
Resort
Islamorada, FL, USA
1.7k from Theater of the Sea 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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Island Time: Partial Ocean View, Ensuite bedrooms, Free Dockage, Htd Pool
Island Time: Partial Ocean View, Ensuite bedrooms, Free Dockage, Htd Pool
Villa
Islamorada, FL, 33036, United States
0.3k from Theater of the Sea center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$613
Average price / night
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Beacon Reef 222
Beacon Reef 222
House
Islamorada, FL, USA
2.5k from Theater of the Sea 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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Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
House
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

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

2 Bedrooms6 Guests
10.0

Exceptional

48 reviews

$450
Average price / night
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Ragged Edge Resort & Marina
Ragged Edge Resort & Marina
Resort
Islamorada, FL, USA
3.1k from Theater of the Sea center

Accommodations, Pools, Resorts, Parking, Lodgings, Places to stay, Family, Self-catering

14 Bedrooms35 Guests
9.1

Superb

157 reviews

$248
Average price / night
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Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
6.0

Review score

1 reviews

$296
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
3.7k from Theater of the Sea 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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Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
New to Booking
$296
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
3.7k from Theater of the Sea 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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Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
8.0

Good

1 reviews

$296
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
3.7k from Theater of the Sea 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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Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$295
Average price / night
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Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom2 Guests
New to Booking
$295
Average price / night
Check Availability
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$295
Average price / night
Check Availability
Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!
Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Balcony, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Housekeeping, Internet

1 Bedroom4 Guests
8.4

Very Good

5 reviews

$222
Average price / night
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Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Pool, Parking
Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Pool, Parking
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Balcony, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Microwave

1 Bedroom4 Guests
8.6

Fabulous

7 reviews

$222
Average price / night
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Beach View Unit in Islamorada! Pets Allowed, Parking, Pool!
Beach View Unit in Islamorada! Pets Allowed, Parking, Pool!
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Balcony, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Microwave

1 Bedroom4 Guests
8.6

Fabulous

22 reviews

$223
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 Theater of the Sea.

Where to stay in Theater of the Sea? Best neighborhoods & areas

Theater of the Sea Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 418 verified vacation rentals with a pool in Theater of the Sea. 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 Theater of the Sea vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $222 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Theater of the Sea 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 Theater of the Sea welcome pets. Currently, 52 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 Theater of the Sea often include additional outdoor features such as Pool, View, and Internet. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Theater of the Sea 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.