Holiday rentals with a hot tub in Vaca Key

5 out of 5 average rating, 63 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

Captains Quarters, Your 4BR Waterfront Oasis on a deep-water ocean canal. This meticulously remodeled home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ Luxury heated pool & spillover spa ⛵ Private 75ft dock with sailing kayaks for ocean adventures 🕹️ Epic game room with Golden Tee, Pack Man, foosball table, Ping Pong & Infinity Game Table 🍳 Outdoor patio with BBQ grill & waterfront dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

A spacious living area features a large sectional sofa with plush cushions and a wooden coffee table at its center. Nearby, a dining table accommodates several chairs. Bright windows allow natural light to fill the room, and a staircase leads to the upper level.

5 out of 5 average rating, 22 reviews

Oceanview Luxury Retreat 12 Guest 6 Beds Pool&Dock

Enjoy Ocean views and stay in luxury at this brand new five bedroom four bathroom Marathon masterpiece including a pool and 40 feet of dockage overlooking the Atlantic Ocean. The spacious kitchen, cocktail lounge and living area with a giant TV make for a wonderful relaxing stay. Five bedrooms and four full bathrooms will accommodate large groups. Upstairs find two master suites and a third suite with direct bathroom access. Unique pool has both sun and shade with optional pool heat for a fee.

An aerial view captures the duplex home situated near a canal with multiple boats docked along the water. The vibrant homes are seen in a tangle of greens and blues, with sandy pathways and lush landscaping complementing the serene coastal environment.

5 out of 5 average rating, 29 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

This 2 bed/2 bath Duplex home is located on the water just 4 homes away from the open Atlantic Ocean. Bring your boat or rent one! Paddle with our 4 comp kayaks right from our dock. Go 8 min drive to Sombrero Beach. We have you covered with comp beach towels and beach chairs. We have fishing rods, nets, underwater green light, outdoor freezer and bait station for you to use while staying in our home. Fish right from your very own dock and cook the fresh catch in our BBQ. VACA-24-53

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5 out of 5 average rating, 56 reviews

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Welcome to Paradise Palms: ⭑ 1750 sqft liveable space on 10,500 sqft estate ⭑ Private home, deck, patio & backyard, overlooking a beautiful scenic landscape ⭑ Crystal pool, hot tub, movie theater, remote workspace, game room with arcade & more ⭑ Secure parking for up to six vehicles, boat trailer parking, RV and EV charging ⭑ 10 min to sombrero beach & just minutes to all island attractions ⭑ Fully stocked kitchen ⭑ Extremely safe neighborhood License #VACA-24-20 License #VACA-24-32

A private dock is seen along a deep water canal, with a boat and jet ski moored nearby. Lush palm trees frame the waterfront space, while a two-story residence with a balcony stands in the background under a clear blue sky.

4.98 out of 5 average rating, 41 reviews

Waterfront home with direct Atlantic Ocean access

Located in Marathon, FL where you are close to local shops, grocery stores, boat ramp, plenty of boat/jet ski/water sport rentals, fishing charters, etc. Enjoy 60 feet of private dockage and a great outdoor area equipped with a grill, bar, sink, outdoor shower, bathroom and furniture. This deep water canal has a straight shot channel that leads you to the Atlantic Ocean and is a short boat ride to the Gulf. Come experience the great fishing and boating Marathon has to offer! VACA-22-137

A renovated house is set on a corner lot, surrounded by palm trees and coral stone landscaping. The exterior features light yellow walls and white accents. A gravel driveway offers ample parking space, complementing the tranquil tropical environment.

4.93 out of 5 average rating, 147 reviews

Marathon Star - home with hot tub

Completely renovated 3 bedroom house in Marathon. Conveniently located near the Florida Keys Aquarium Encounters and the Marathon Lady. Enjoy a private hot tub and outdoor grill after a long day of Florida sunshine! Our home is not on the water but there is plenty of parking space for your boat trailer if needed. We hope our wonderful space becomes a great home away from home. ***Please see below for more information regarding hurricane season cancellation policy.

A wooden dock extends over calm waters, featuring several brown adirondack chairs positioned for relaxation. Lush palm trees and tropical foliage line the shore, while a glimpse of a covered seating area and distant homes adds to the coastal atmosphere.

4.98 out of 5 average rating, 44 reviews

Oceanfront w/ Dock, Hot Tub & Secluded

Buchanan Keys Cottage Take a step back into “Old Keys” living. Once Upon A Tide; there was a sense of tranquility & peacefulness found throughout the Keys, like the one you will uncover when choosing to stay at this private, serene, 1/1 oceanfront cottage. Located on Grassy Key, this beautiful home is just 10 minutes from the City of Marathon. Far enough to be away from the hustle & bustle, but close enough to make a grocery/store run a “Keys breeze”.

A tranquil pool is surrounded by lush palm trees, offering a serene atmosphere. The water reflects sunlight, while seating options are provided by the poolside. The design features a curved edge and a spa section, creating an inviting outdoor retreat.

5 out of 5 average rating, 11 reviews

The Roseate House at Grassy Key Lic. #VACA-25-222

Lic. #VACA-25-222: Make The Roseate House at Grassy Key your next get away. Relax, fish, swim and explore at your own personal resort. The home is perfect for couples, family or girls retreat. Families return year after year to create their memories. Honeymooners appreciate the privacy as well as the attention to detail. Come live among the treetops in this vintage conch Key West style cottage situated half way between Key Largo and Key West.

A private backyard features a hot tub and a shallow pool, surrounded by tropical greenery. Lounge chairs in teal are positioned nearby, and a grill is placed on the concrete patio. The canal is visible in the background, lined with palm trees.

4.93 out of 5 average rating, 44 reviews

Waterfront w/pool and hot tub

Professionally decorated, spacious, canal view keys home located in Key Colony Beach, the “Gem” of the Florida Keys. Featuring 2BR 2BA accommodating up to 6 ppl in a large & open living room & backyard, provided w/2 bikes, 2kayaks, grill, and 2 minutes walk to Sunset park, it is the perfect Florida Keys getaway for your family. This location is in the heart of the Florida Keys only 45 minutes from Key West and 35 minutes to Islamorada.

4.95 out of 5 average rating, 128 reviews

The living area features contemporary furnishings and large windows, allowing for bright natural light and views of the waterways. A dining table is positioned beside the seating area. The spacious lanai showcases an outdoor dining setup with a view of the dock and water.

Home in Key Colony Beach

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

4.95 out of 5 average rating, 140 reviews

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!

A spacious canal front home is displayed, featuring a large outdoor pool and spa area. The porch overlooks the water, surrounded by lush greenery. Lounge chairs line the pool deck, with a private dock accessible directly from the pool area.