Holiday rentals in Lower Sugarloaf Key

Key Lime Retreat

Weekly Treat! Downtown vacation experience for entire family. Located in the hearth of Historic Seaport location in Key West. Conveniently walking distance to Duval St shopping, offices, entertainment, restaurants, bars, and everything Key West has to offer. There is not much to say about this condo, The location talks for itself! It’s a must have Key West experience on a quite gated community just steps away from Duval St. It’s a true Gem to experience the Key West living to the fullest extend.

Yellow Home Free Pontoon Rental! See details

If you book your stay for the days shown below March 30th - April 15th, 2025 April 23rd - May 3rd,  2025 May 17th - May 31st, 2025 June 6th - June 13th, 2025 Receive a free 2 day boat rental for a week reservation, 1 day for a 3 days or more reservation. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

Ocean Side Paradise Awaits!

This gated oceanfront property spans over 7 acres and boasts an Olympic size pool overlooking the mesmerizing Atlantic Ocean. Take advantage of the many tiki huts, fishing dock, air-conditioned clubhouse, and grilling station to cook up your fresh catch. Our turnkey townhouse is perfect for a short vacation or a longer-term stay. Everything in the complex, from the facilities to the furnishings, is brand new. Don't miss the opportunity to experience paradise at its finest. Book your stay now!

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach

No hidden fees! Casa Azul blends luxury and laid-back island vibes in the heart of Key Largo. With Superhost status and hundreds of 5-star reviews, a perfect escape. Voted the #1 Vacation Rental in Key Largo, it’s ideal for families, couples, and groups alike. Enjoy a free golf cart, fast Wi-Fi, 2 pools, private beach, saltwater lagoon, kayaks, tennis and pickleball courts with gear, marina access, boat ramp, trailer parking, and optional slip rentals. Salt Life meets luxury - this is the one.

2/1 Oceanfront Apartment with Dockage

The Seaside Vista is a luxurious ocean front retreat located in Key Largo. Only 1 hour from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From great dining, to water sports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled , enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer. MC Permit #: 21302180

Modern and Coastal Ocean Pointe 2307

Are you looking for a Caribbean Vacation in a tropical resort without leaving the USA? Look no further than our Ocean view 2 bedroom and 2 bath condo at Ocean Pointe Suites! Our property offers: 24 hour front gate security, Heated Junior Olympic Pool with 15 person hot tub, tropical Beach, Marina, Tennis/Pickle ball courts. Enjoy our newly re opened ISLAND GRILL pool bar! We are located 60 miles from Miami International Airport and 90 miles from Fort Lauderdale International Airport.

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

This mid-rise home is fully furnished with high ceilings throughout! The living room offers a flat screen television with sleeper sofa. Master bedroom features a queen bed with full bathroom and flat screen television. Guest bedroom features a full size bed and half bath. Additional amenities include large open porch with table and chairs, gas grill and central air conditioning and heat. Free WiFi offered in unit and in Community Recreation Center.

Oceanfront Resort W/Indoor Pickleball - Spacious!

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. This 3/3.5 villa is located in Key Largo's most upscale oceanfront resort. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simply desire the very best in luxury accommodations.

Florida Keys Getaway - Slps 4 - Ocean View

Check out this recently remodeled 1-bedroom condo with relaxing and tasteful beach decor - perfect for your Keys Getaway. Ideally located between Key Largo and Islamorada, it offers the best of both worlds! Ocean Pointe is an oceanfront condo property that's just steps away from all the Keys have to offer - the world's best fishing, diving, snorkeling, paddle boarding, and kayaking.