Serviced apartment vacation rentals in Key West

Ideal Location! Pets Allowed, Pool, Free Breakfast

Islamorada, a popular tropical holiday spot conveniently located about an hour south of Miami. It is renowned for its upscale, small-town vibe, picturesque bay and ocean vistas, year-round sunlight, boating, fishing, locally owned restaurants, and charming shops and galleries. Also referred to as the "Sport Fishing Capital of the World,", Islamorada draws anglers of all abilities. There is so much to discover in Islamorada, and we’re the perfect place to stay so you can experience it all.

Beach House Retreat + Premium Amenities, 2BR Condo

Indulge in the exclusive privilege of the resort’s private white sand beach, complete with BBQ grills, for the ultimate seaside retreat. Watersport rentals available Feel the tropical breeze as you dip into the zero-entry lagoon pool or join in fun games like table tennis, cornhole, and foosball. Enjoy delicious bites at Jimmy’s Ocean Blue Tiki Hut. Unlock $500-$1000 in SAVINGS on select 7-night reservations with 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢. PROPERTY REQUIRES SUNDAY-SUNDAY reservations.

Private Beach House Resort Oasis, 2-Bedroom Suite

Indulge in the exclusive privilege of the resort’s private white sand beach, complete with BBQ grills, for the ultimate seaside retreat. Watersport rentals available Feel the tropical breeze as you dip into the zero-entry lagoon pool or join in fun games like table tennis, cornhole, and foosball. Enjoy delicious bites at Jimmy’s Ocean Blue Tiki Hut. Unlock $500-$1000 in SAVINGS on select 7-night reservations with 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢. PROPERTY REQUIRES SUNDAY-SUNDAY reservations.

Islamorada Stay! Free Breakfast | Pool & Parking!

Islamorada, a popular tropical holiday spot conveniently located about an hour south of Miami. It is renowned for its upscale, small-town vibe, picturesque bay and ocean vistas, year-round sunlight, boating, fishing, locally owned restaurants, and charming shops and galleries. Also referred to as the "Sport Fishing Capital of the World,", Islamorada draws anglers of all abilities. There is so much to discover in Islamorada, and we’re the perfect place to stay so you can experience it all.

Convenient Location! Free Parking, Breakfast, Pool

Islamorada, a popular tropical holiday spot conveniently located about an hour south of Miami. It is renowned for its upscale, small-town vibe, picturesque bay and ocean vistas, year-round sunlight, boating, fishing, locally owned restaurants, and charming shops and galleries. Also referred to as the "Sport Fishing Capital of the World,", Islamorada draws anglers of all abilities. There is so much to discover in Islamorada, and we’re the perfect place to stay so you can experience it all.

Near Duval-Waterfront Sunset Harbor Resort

Imbibe the relaxed Key West lifestyle from a coveted location in the Heart of Old Town at this fantastic waterfront resort overlooking the Gulf of Mexico. Access to Resort Amenities included! Additional $500-$1000 SAVINGS available with 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 on certain 7-Night stays. All reservations require a FRI-FRI, SAT-SAT OR SUN-SUN STAY SHORT STAYS: 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 can provide shorter stays. Some stays shorter than 7-Nights *may incur a higher nightly rate

Near Southernmost Pointe Windward Resort+Amenities

Immerse yourself in the crystal-clear waters, our infinity pool calls your name or unwind at in the whirlpool spa. Challenge friends and family to a spirited game of beach volleyball. And if you're feeling competitive, our shuffleboard, ping pong, foosball, and pool tables await your skills. Additional $500-$1000 SAVINGS available with 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 on certain 7-Night stays, short stays or custom dates. All reservations require a FRI-FRI, SAT-SAT OR SUN-SUN STAY.

WATERFRONT GALLEON BEACH & MARINA, 2BR+Amenities

Perfectly nestled in the heart of Old Town Key West, overlooking the Gulf of Mexico in historic Old Town, your vacation resort residence puts you in an ideal location for enjoying the many charms of Key West. Sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. 7-Nights Stay Required [SATURDAY - SATURDAY STAY ONLY] SPECIAL RATES MAY BE AVAILABLE THROUGH CHIMERA VACATIONS

Waterfront Marina 2BR Mallory Condo+Amenities

Thank you for visiting Chimera Vacations 7-Night Required (Saturday-Saturday Check-In/Check-Out) Rejuvenate in this lush tropical surroundings located near the southernmost tip of Florida. Guest will have access to 2 Swimming Pools, a Whirlpool Hot Tub, Clubhouse, Barbecue Grill Area, a playground for younger guests. Enjoy the marina with available boat slips. The guest services desk is always at hand to help you arrange any and all island activities.

Knight's Key Suites Deluxe Double Room w/ Kitchen

One-of-a-kind place accommodations located next to the 7-Mile Bridge. These rooms feature two full beds that can accommodate up to four people. The room comes equipped with a kitchen. Perfect for long or short-term stays! Dear guest, we’re sorry to inform you that, due to unexpected circumstances beyond our control, the pool will be closed until Saturday 8/1/26. A significant leak was found and emergency repairs are necessary to fix the problem.

Knight's Key Suites Deluxe King Room w/ Kitchen

One-of-a-kind place accommodations located next to the 7-Mile Bridge. These rooms feature one king bed that can accommodate up to two people. The room comes equipped with a kitchen. Perfect for long or short-term stays! Dear guest, we’re sorry to inform you that, due to unexpected circumstances beyond our control, the pool will be closed until Saturday 8/1/26. A significant leak was found and emergency repairs are necessary to fix the problem.

Coconut Mallory Resort: 2-BR, sleep 6, Kitchen

Coconut Mallory Resort and Marina: 2-Bedrooms, sleep 6, Full Kitchen. Fixed week rental, 7 nights blocks, Friday or Saturday changeover only. This is a 2 bedroom, 2 bathroom condo unit that features a full kitchen and a flat panel television. All newly refurbished and decorated in an island inspired elegance. The unit also has a private balcony, access to both resort pools, and the resort marina. Maximum occupancy of six.