Top 30 Best Beach vacation rentals with pool in Islamorada, Florida

Latitude Key Vacations is a premier real estate and travel agency located at 3324 Northeast 32nd Street in Fort Lauderdale, Florida, United States.

Experience the ultimate Florida Keys vacation at Angler's Reef Resort Select Rentals by KeysCaribbean.

Anglers Reef Vacation Rental is a premier real estate and travel agency located at 109 Anglers Way in Islamorada, Florida.

Barefeet Vacation Rentals is a real estate and travel agency located at 103400 Overseas Highway in Key Largo, Florida.

Ocean Oasis at Ocean Pointe is a luxurious vacation destination located in Tavernier, Florida. This stunning institution offers a range of amenities including a pool, Jacuzzi, tennis and pickleball courts, a private beach, and a marina.

Islamorada Ocean Oasis is a premier real estate and travel agency located at 75831 Overseas Highway in Islamorada, Florida.

Sun Outdoors Islamorada is a charming lodging and RV park located at 87395 Old Highway in Islamorada, Florida, United States.

Located at 83409 Overseas Highway in Islamorada, Florida, the Chesapeake Beach Resort is a stunning seaside lodging destination that exceeds all expectations.

Coastal Vacation Rentals of the Florida Keys is a premier real estate and travel agency located at 82889 Overseas Highway in Islamorada, Florida, United States.

Keys Holiday Rentals is a premier real estate and travel agency located in the beautiful town of Islamorada, Florida.

Islamorada Vacation Rentals is a premier real estate and travel agency located in the picturesque town of Islamorada, Florida.

Freewheeler Vacations is a premier real estate and travel agency located in the beautiful coastal town of Islamorada, Florida.

Tropical Paradise in Venetian Shores is a luxurious retreat located at 141 Stromboli Drive in Islamorada, Florida. This stunning property offers guests a true taste of paradise with its lush tropical surroundings and breathtaking views.

Beach Park is a stunning oceanfront park located at 87000 Overseas Highway in Islamorada, Florida.

Island Villa Rental Properties is a premier real estate and travel agency located at 81681 Old Highway in Islamorada, Florida, United States.

The Beach House at Tarpon Point is a luxurious oceanfront home located at 77521 Overseas Highway in Islamorada, Florida.

Islamorada Vacation Rental is a premier lodging option located at 101 Leoni Drive in Islamorada, Florida.

Islamorada Vacation Rentals is a premier real estate agency located at 81610 Overseas Highway in Islamorada, Florida.

Florida Keys Vacation Rentals Inc. is a premier real estate and travel agency located at 85996 Overseas Highway in Islamorada, Florida.

Island Bay Resort is a tropical oasis located at 92530 Overseas Highway in Tavernier, Florida, United States. Our beachfront location on the Florida Bay offers stunning sunsets and a relaxing atmosphere surrounded by palm trees and flowering plants.

Little Basin Villas is a premier real estate and travel agency located in the picturesque Islamorada, Florida. Situated at 84 Johnston Road, our institution offers luxurious villas for rent or purchase in this stunning seaside town.

The Caribbean Resort, located at 117 Carroll Street in Islamorada, Florida, is a charming lodging option that offers a taste of the Caribbean right in the heart of the United States.

Coral Bay Resort, located at 75690 Overseas Highway in Islamorada, Florida, offers a relaxing and picturesque lodging experience. Guests can unwind in the fresh water heated pool after a day of exploring the waters.

Topsiders Resort is a charming lodging establishment located at 75500 Overseas Highway in the picturesque town of Islamorada, Florida. This tropical oasis offers guests a relaxing and comfortable stay in the heart of the Florida Keys.

Drop Anchor Resort & Marina is a charming lodging establishment located at 84959 Overseas Highway in the beautiful Islamorada, Florida.

Located at 80401 Old Highway in Islamorada, Florida, the Pines and Palms Resort is a charming lodging institution that offers boutique-style accommodations right on the Atlantic Ocean.

Executive Bay Club is a premier institution located at 87200 Overseas Highway in Islamorada, Florida. It offers a luxurious and exclusive experience for its members, featuring top-notch amenities and services.

Located at 81200 Overseas Highway in Islamorada, Florida, the Kon-Tiki Resort is a charming lodging institution that offers a unique and unforgettable vacation experience.

Located at 80241 Overseas Highway in Islamorada, Florida, La Siesta Resort & Villas offers a tropical island style getaway with spacious guest rooms, beachside cottages, and private vacation homes.

Breezy Palms Resort is a charming lodging destination located in the beautiful Islamorada, Florida. Situated at 80015 U.S. 1, this tropical oasis offers guests a relaxing and unforgettable experience in the heart of the Florida Keys.