Holiday rentals with a sauna in Key West

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

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.

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!

Waterfront Sunset Harbor Club Resort+Amenites. 1BR

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. And with our Inspired Experiences program, you can leave Key West feeling fulfilled. Additional $500-$1000 SAVINGS available with 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 on certain 7-Night stays. All reservations require SUNDAY-SUNDAY check-in/check-out

Luxury on the Sea! 50' motor yacht in resort!

Enjoy exclusive use of this 50-foot yacht all to yourselves, with the opportunity to get close to ocean life. This yacht is docked at the Stock Island Marina, with complimentary use of a stunning waterfront swimming pool, pool side bar, sauna, private beach, fitness center, & a waterfront tiki hut. Come and go on the yacht anytime, day or night. Participating in an ocean excursion on this yacht is mandatory & comes at an extra charge. Inquire here about our other yachts in our fleet

Key Colony Beach canal home with Cabana Club

Located in the Gem of the Florida keys this home has everything you'll need to enjoy your tropical getaway. This 3 bedroom 2 bath canal residence has 2 queen and 1 King bed each with 50" smart TVs and a larger 65" TV in family room. Enjoy dining in one of the many restaurants in the area or prepare a home cooked meal in our large kitchen open to dining and family room. The patio offers 37.5' dock and sitting area to enjoy the sunny outdoors. Cabana Club included

Beach House Resort+Amenites, 2BR

We look forward to welcoming you to this rare BEACH Resort retreat. Feel the tropical breeze from the zero-entry lagoon pool; play table tennis, cornhole, and foosball; feast at Jimmy’s Ocean Blue Tiki Hut; or simply enjoy the Gulf of Mexico views from 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.

Feb. Save $!$ Oceanfront 4 Bikes/2Kayaks. KING bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Oceanview condo w/pool, jacuzzi

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 !

Key West Condo with Balcony Ocean View

Enjoy beautiful views of the Atlantic Ocean while enjoying a private balcony. Newly re-modeled kitchen. Air conditioning and ceiling fans located in every room. Amenities include pool, hot tub, and tennis courts. Just a few steps across the street in Smathers Beach which offers beach chairs, umbrellas, paddle boards, kayaks and sailboats available for rent. Two vehicles max. NO TRAILERS of any kind allowed to park on property.

Couples Getaway, Suites-Marlin Bay Resort & Marina

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.

Serenity by the Sea | La Brisa

Welcome to your island escape! This 2BR/2BA condo in the gated La Brisa complex is across from Smathers Beach and just a short ride to Duval Street. Enjoy an open-concept layout, coastal-chic décor, full kitchen, private balcony with salt pond views, and resort-style amenities including a 24-hr pool, hot tub, sauna, tennis, EV charging, and more. Perfect for beach days or exploring Key West—book your stay today!