Anchors Aweigh 10% off Fall 2025!

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.

Welcome to Anchors Aweigh – Your Oceanfront Escape on Summerland Key!

Discover the perfect blend of relaxation and adventure at Anchors Aweigh, a stunning open-water retreat designed for families and friends. With two distinct living areas, this spacious home is ideal for multiple families or extended stays. Unwind as you watch the sunset over the water, sip a refreshing drink under the Tiki hut, or take a dip in the inviting pool. Whether you're basking in the sun, exploring the crystal-clear waters of Niles Channel, or simply enjoying the ocean breeze, every moment here is pure bliss. For those seeking adventure, you're just 30 minutes from Key West and Marathon, where endless dining, shopping, and outdoor activities await. Make Anchors Aweigh your home away from home—where breathtaking views, coastal comfort, and unforgettable memories come together. Book your stay today!

SLEEPS MAXIMUM OF 10 GUESTS (there are no interior stairs between levels, only access is via exterior stairs):

Bedroom 1 (Upstairs): King Bed, Smart TV (no cable/satellite TV)

Bedroom 2 (Upstairs): Queen Bed, Smart TV (no cable/satellite TV)

Bedroom 3 (Downstairs): Two Queen Beds

Living Room (Upstairs): Sofa, Loveseat, Chair, Smart TV (no cable/satellite TV)

Living Room (Downstairs): Sofa with Pull Out Queen Bed, Smart TV (no cable/satellite TV)

Kitchen (Upstairs): Nicely equipped (all things necessary to prepare and serve a meal)

Kitchenette (Downstairs): Lightly equipped (no stove/oven)

AMENITIES:

- Saltwater Heated Pool (20'x12', ~4' depth, heated to ~85 degrees Nov-Apr)

- 60' of Waterfront, 180' pier with ~32' of dockage and 3-4' depth at end of pier (boat lift not available for guest use)

- Tiki

- Outdoor Seating

- Propane BBQ Grill

- Parking for a maximum of 4 vehicles (including boat trailers) on the property. RVs may not be parked on the property.

- Outdoor Shower (cold water only)

- Linen's and towels provided

IMPORTANT POLICIES FOR YOUR STAY:

Age & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing.

Peak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking.

Pet Policy: Up to two friendly and well-behaved dogs will be considered with prior approval, payment of a $10/night pet fee, and registration with a third-party pet screening service (fee applies for pets, free for service animals). Please review our pet policy before booking—we will provide the registration link after you confirm your reservation.

Smoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment.

Mid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay.

Boating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations.

Local Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure.

Construction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction.

Photo Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time.

Security Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the front driveway, and pier. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.