Holiday rentals with a sauna in Key West

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

SEPT/OCT. Save$Oceanfront 4 BIKE/2 Kayak KING Bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. At MM# 23 only 25min to Key West. In a gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C *Fully equipped kitchen *Includes grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library. Too much to list! WE WILL NEED YOUR EMAIL WHEN YOU CONFIRM THE BOOKING IN ORDER TO SEND YOU THE REGISTRATION FORMS AND THE RULE PACKET.

Dock Pool Ramp Jacuzzi Ocean Views Kayaks

Newer constructed private home with a 65 ft. dock, pool, jacuzzi, ramp, instant ocean access, stunning ocean views. The house includes 3 bedrooms with 2 bathrooms. The master bedroom has a queen bed and a private bathroom, the second bedroom has a queen bed, and the third bedroom has a queen bed with a full-size trundle. The property boasts a spacious kitchen and living area, with a BBQ overlooking the ocean and canal from the covered patio. Plenty of parking for trucks and trailers. VACA-22-31

Beautiful 43 ' sportfish yacht

Come enjoy a yacht stay at Stock Island Yacht Club! Gorgeous facilities with Beach, pool, bar, and a gym!. The boat does not go out during the booking, but we can arrange a charter on it or other boats. We also rent street legal golf carts, outboard boats, and private backcountry sandbar charters. Come enjoy paradise on the Lisa Lynn! The marina has a small but gorgeous beach, amazing pool, and great tiki hut area. The tiki is at the end of a mangrove boardwalk, great place for a morning walk!

Near Duval, Waterfront Sunset Resort+Amenities

With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultimate island retreat. Mere minutes from iconic area attractions, it’s also a haven for relaxation with its tranquil pool and whirlpool spa. Check out 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 for an additional $500-$1000 SAVINGS on certain 7-Night stays. Some custom dates can be arranged for you, please inquire Reservations require a SUNDAY-SUNDAY check-in/check-out.

Spacious 3BR Villa in Duck Key | Fishing + Pools

This spacious three-bedroom villa offers a comfortable two-story layout ideal for families or groups seeking extra room during their Florida Keys getaway. The king master bedroom provides a relaxing retreat, while the additional bedrooms offer flexible sleeping arrangements. A full kitchen, dining area, and bright living room with a sleeper sofa make gathering easy. Enjoy a private balcony or patio and convenient access to all Hawks Cay Resort amenities!

Oceanview condo w/pool, jacuzzi and tennis court

Plan your next vacation at this peaceful, breathtaking, Ocean-view condo at La Brisa resort located across the street from largest beach on the island, Smathers Beach. Take advantage of the pool, tennis courts, hot tub, and sauna or just enjoy the Atlantic Ocean view from your private balcony. The condo is in a gated community with private parking and elevator access. Bring your family and lets enjoy your vacation in Key West 🌴☀️ No pets allowed !

Wide Canal Home with Cabana Club & Ice Machine

Relax at this wide canal-front Key Colony Beach home with Cabana Club access, space for up to 6 guests, a peaceful waterfront setting, BBQ grill, and commercial 500 lb ice machine. Enjoy mornings by the canal, afternoons at the Cabana Club pool and beach, and evenings near Sunset Park or local waterfront restaurants. A private boat lift is on-site but is not available for guest use; overnight boat dockage is not offered.

Pet & Family Friendly, Sleeps 8 - Marlin Bay

Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort featuring 13 luxury vacation homes, 74 private marina slips and a centrally located pool deck and clubhouse. We provide unparalleled service in an intimate setting allowing you to relax and unwind. We are located in Marathon in The Middle Keys, so you can easily explore all that The Keys have to offer.

Ashe Mare Villa | Waterfront + Water Access

Welcome to Ashe Mare Villa — Where Sunset Meets Soul, a waterfront retreat in Duck Key just minutes from Marathon. This 2-bedroom, 2.5-bath villa sleeps up to 6 with two queen en-suite bedrooms and a queen sofa bed. Enjoy a private waterfront patio, direct water access for swimming, fishing and launching kayaks, a full kitchen, Wi-Fi, Smart TVs, and easy access to the best of the Florida Keys.

Galleon Resort - Walk to Duval & Mallory Square!

Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the Jacuzzi or sauna during your stay or work out in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.

Affordable Beachfront Luxury Condo Sleeps 6

My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!