Islamorada, Florida

Wander Islamorada Retreat

7 bedrooms7 beds5 baths15 guests4.9 (7)

About the property

Wander Islamorada Retreat offers an exceptional collection of amenities designed for comfort, entertainment, and relaxation. Outside, guests can enjoy a stunning heated waterfront pool surrounded by a tropical lounge area and a tiki cabana for shaded relaxation. The property features a 35-foot-wide deep-water dock, perfect for accommodating larger boats—an especially valuable feature for Islamorada travelers looking to explore the Keys by water or enjoy world-class fishing and boating. Guests also have access to two paddleboards and two kayaks for on-the-water adventures, as well as ample parking with dedicated boat trailer space. Additional conveniences include laundry facilities, elegant indoor and outdoor dining areas, and thoughtfully designed spaces that blend island charm with elevated comfort.

Wander Islamorada Retreat offers an exceptional collection of amenities designed for comfort, entertainment, and relaxation. Outside, guests can enjoy a stunning heated waterfront pool surrounded by a tropical lounge area and a tiki cabana for shaded relaxation. The property features a 35-foot-wide deep-water dock, perfect for accommodating larger boats—an especially valuable feature for Islamorada travelers looking to explore the Keys by water or enjoy world-class fishing and boating. Guests also have access to two paddleboards and two kayaks for on-the-water adventures, as well as ample parking with dedicated boat trailer space. Additional conveniences include laundry facilities, elegant indoor and outdoor dining areas, and thoughtfully designed spaces that blend island charm with elevated comfort.

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jun 30, 2026$1,350.50Not Available7
Jul 1, 2026$1,443Not Available7
Jul 2, 2026$2,316.50Not Available7
Jul 3, 2026$2,316.50Not Available7
Jul 4, 2026$2,316.50Not Available7
Jul 5, 2026$2,316.50Not Available7
Jul 6, 2026$1,350.50Available7
Jul 7, 2026$1,350.50Available7
Jul 8, 2026$1,350.50Available7
Jul 9, 2026$1,350.50Not Available7
Jul 10, 2026$1,496.50Not Available7
Jul 11, 2026$1,599Not Available7
Jul 12, 2026$1,443Not Available7
Jul 13, 2026$1,443Not Available7
Jul 14, 2026$1,443Not Available7
Jul 15, 2026$1,443Not Available7
Jul 16, 2026$1,443Available7
Jul 17, 2026$1,599Available7
Jul 18, 2026$1,517Not Available7
Jul 19, 2026$1,461.50Not Available7
Jul 20, 2026$1,461.50Not Available7
Jul 21, 2026$1,461.50Not Available7
Jul 22, 2026$1,480Not Available7
Jul 23, 2026$1,480Not Available7
Jul 24, 2026$1,640Not Available7
Jul 25, 2026$1,640Not Available7
Jul 26, 2026$1,498.50Not Available7
Jul 27, 2026$1,498.50Not Available7
Jul 28, 2026$1,517Not Available7
Jul 29, 2026$1,517Not Available7
Jul 30, 2026$1,535.50Not Available7
Jul 31, 2026$1,722Not Available7
Aug 1, 2026$1,424.37Not Available7
Aug 2, 2026$1,328Not Available7
Aug 3, 2026$1,344.60Not Available7
Aug 4, 2026$1,344.60Not Available7
Aug 5, 2026$1,361.20Not Available7
Aug 6, 2026$1,377.80Not Available7
Aug 7, 2026$1,514.52Not Available7
Aug 8, 2026$1,514.52Available7
Aug 9, 2026$1,411Available7
Aug 10, 2026$1,427.60Available7
Aug 11, 2026$1,444.20Available7
Aug 12, 2026$1,444.20Available7
Aug 13, 2026$1,460.80Available7
Aug 14, 2026$1,586.64Available7
Aug 15, 2026$1,604.67Available7
Aug 16, 2026$1,477.40Available7
Aug 17, 2026$1,494Available7
Aug 18, 2026$1,494Available7
Aug 19, 2026$1,494Available7
Aug 20, 2026$1,510.60Available7
Aug 21, 2026$1,640.73Available7
Aug 22, 2026$1,640.73Available7
Aug 23, 2026$1,510.60Available7
Aug 24, 2026$1,510.60Available7
Aug 25, 2026$1,527.20Available7
Aug 26, 2026$1,527.20Available7
Aug 27, 2026$1,527.20Available7
Aug 28, 2026$1,658.76Available7
Aug 29, 2026$1,658.76Available7
Aug 30, 2026$1,527.20Available7
Aug 31, 2026$1,527.20Available7
Sep 1, 2026$1,431.52Available7
Sep 2, 2026$1,431.52Available7
Sep 3, 2026$1,431.52Available7
Sep 4, 2026$2,030.08Available7
Sep 5, 2026$2,030.08Available7
Sep 6, 2026$2,030.08Available7
Sep 7, 2026$2,030.08Available7
Sep 8, 2026$1,431.52Available7
Sep 9, 2026$1,431.52Available7
Sep 10, 2026$1,431.52Available7
Sep 11, 2026$1,530.88Available7
Sep 12, 2026$1,530.88Available7
Sep 13, 2026$1,431.52Available7
Sep 14, 2026$1,431.52Available7
Sep 15, 2026$1,431.52Available7
Sep 16, 2026$1,431.52Available7
Sep 17, 2026$1,431.52Available7
Sep 18, 2026$1,530.88Available7
Sep 19, 2026$1,530.88Available7
Sep 20, 2026$1,431.52Available7
Sep 21, 2026$1,431.52Available7
Sep 22, 2026$1,431.52Available7
Sep 23, 2026$1,431.52Available7
Sep 24, 2026$1,431.52Available7
Sep 25, 2026$1,530.88Available7
Sep 26, 2026$1,530.88Available7
Sep 27, 2026$1,431.52Available7
Sep 28, 2026$1,431.52Available7

Amenities

Waterfront
Ocean view
Boat dock
Pool outdoor
Fire pit
BBQ Area
Patio
Balcony

4.9 · 7 reviews

C
coolke77
May 2026

Visits from the manatees, tarpon fishing, enjoying the sunsets, paddling the mangroves from the dock and to Lorelei’s for a cocktail, evenings in the tiki hut laughing with family, pool games, snapper fishing from the dock, catching up and relaxing with family in a beautifully designed home.

S
sylviaw62021
April 2026

C
Christopher g.
April 2026

The house was absolutely perfect for our group! We enjoyed the cleanliness, the location, the dock and private pool! The overall experience was a 15 out of 10! We would definitely recommend Wander as a management company to anyone in the future.

Where you'll be

Islamorada, Florida, 33036, United States

Set in the heart of the Florida Keys, this area offers endless opportunities for relaxation and adventure. Spend your days snorkeling or diving in the crystal-clear waters of the nearby reefs, kayaking through mangrove tunnels, or embarking on a world-class fishing excursion in the sportfishing capital of the world. Explore the local marinas, art galleries, and boutiques that showcase the island’s creative spirit, or enjoy fresh seafood and tropical cocktails at vibrant waterfront restaurants. For a touch of nature, visit the nearby parks and beaches for paddleboarding, sunset walks, and dolphin spotting.

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Contact us for cancellation policy details prior to booking.

Property rules

Not suitable for children (2–12 years).
Not suitable for infants (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 15 guests.