Vacation rentals with outdoor seating in Key West

5 out of 5 average rating, 5 reviews

A spacious outdoor area features a large wooden swim spa, framed by vibrant greenery and decorative accents. A sun umbrella provides shade over one side, while light-colored tiles and wooden decking surround the spa, creating a relaxing ambiance. The sky is clear with soft clouds.

Home in Key Colony Beach

Huge Swim Spa~ Incredible Special Fall Pricing

3 Bedroom~ 2 Bath Duplex With Outdoor Solar Shower, on a Deep Water Canal in Key Colony Beach. Near The Vaca Cut Makes For Easy Access To The Gulf Of Mexico or Atlantic Ocean. Boat Dockage for up to a 34' Boat. Golf Course, Pickle Ball~Tennis Courts, and Great Playground. We have a Large Swim Spa in The Private Garden, Arcade Game Room~Ice Maker, Paddle Board, 2 Kayaks, 4 Fishing Rods & Bait, Margarita Machine, Outdoor Shower. Cabana Club Membership With Free Beach/ Ocean Access & Huge Pool.

A serene view overlooks the water at sunrise, with soft pastels reflecting on the surface. A white patio table and chairs are positioned under the covered porch, inviting relaxation. The horizon features gentle clouds and distant islands, creating a peaceful atmosphere.

4.91 out of 5 average rating, 33 reviews

Rise And Shine On The Water

Spectacular sunrise view! Room to park one vehicle, but we do have a free overflow lot if needed. Community amenities include tennis, pickle ball, bocce ball, heated pool, hot tub, designated swim area, pool table, ping pong, & darts. We provide bedding, towels, pots & pans. TV in living room & one bedroom. We will also have boat bumpers installed all along the concrete dock that will accommodate a 40' boat. We offer 100% money back if your rental is in the projection cone of a named hurricane.

An aerial view presents the cozy Venture Out Cottage alongside open water, surrounded by several charming homes. The structure features a light-colored exterior with a sloped roof, while nearby palm trees add a touch of greenery to the landscape.

4.83 out of 5 average rating, 64 reviews

Waterfront Venture Out Home

MANDATORY 125$ FEE NOT INCLUDED. PAID DIRECT TO VENTURE OUT COMMUNITY UPON ARRIVAL. Open water views from cozy Venture Out Cottage. Venture out community offers many amenities including Heated Pool, Hot Tub, Basketball Courts, Tennis Courts, Marina, Boat Ramp, Private Convenience Store, Children's Pool, Bath Houses, Laundry Facilities, Fish Cleaning Station, Horseshoes, Children's Play Area, Bocce Ball, 24 Hour Gated Security, Salt Water Swimming Area, Recreation Hall and Pickle Ball Court.

Tiny home in Big Pine Key

A covered patio area features a light wooden floor and is furnished with a white table and colored chairs. A ceiling fan is mounted above, and tropical plants surround the space, providing a natural ambiance. The entrance is accessed by a small set of steps.

4.93 out of 5 average rating, 74 reviews

Tiny Fish Haus

Come experience Tiny Home Living in this Park Model RV right next to the National Key Deer Refuge! . Relax on our covered patio next to a large Saltwater Swimming Pool, Cook dinner on a Blackstone grill , enjoy WIFI, Games, a Flat Screen TV , we have Premium Organic Bedding on our Queen beds for comfort. Turkish Towels for bath and beach..explore Big Pine Key with our 2 bicycles that are included .AirPurifier for clean air inside. 28 Miles to Key West. Keys Shuttle located next to our park

Condo in Key Colony Beach

A bright studio interior features two queen beds with white bedding and decorative orange pillows. Natural light enters through large windows, offering a view of the ocean. A colorful sofa and vibrant decor enhance the welcoming atmosphere.

4.96 out of 5 average rating, 253 reviews

Amazing Ocean Front Views Key Colony Beach

Ocean front Florida Keys Studio Condo in Key Colony Beach with private balcony, heated pool and sandy beach. Continental Inn Unit #40 is a studio condo with a tropical interior featuring 2 queen beds and kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

5 out of 5 average rating, 34 reviews

A modern two-story home features a clean white exterior with navy blue accents. A set of black stairs leads to a covered balcony adorned with potted plants. Large windows allow natural light to enter, while a gravel driveway provides ample space in front.

Home in Marathon

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

4.85 out of 5 average rating, 95 reviews

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

4.86 out of 5 average rating, 178 reviews

A clear blue pool is framed by palm trees and sun loungers in various shades of blue and green. A shaded umbrella provides cool relief over seating areas, with a charming green cottage visible in the background, surrounded by lush greenery.

Townhouse in Key West

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

4.69 out of 5 average rating, 16 reviews

A private balcony is furnished with a glass-top table and woven chairs, offering a serene view of palm trees and a sandy beach area. The calm water reflects a clear sky, creating a peaceful atmosphere for relaxation.

Home in Marathon

#7 Waterfront 4Bed 3Bath Pool Home

🌸Home #7 "BEACHY🏖KEEN" Full WATERFRONT View over the docks and beach and Ocean!🌸 Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming Pool 🤿and BBQ Patio. Includes Private Guest Beach🏖 with Kayaks and Paddle boards and Private powered ⛵Boat Dock right on the Gulf of Mexico! 🌅🥂 Kick back and completely🍷 relax in our Beautiful and 🍹comfortable home! Perfect for 🍻Adults and kids of all Ages!

4.96 out of 5 average rating, 112 reviews

A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.

Home in Marathon

Anglers Terrace, Condé Nast Traveler's Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

4.76 out of 5 average rating, 103 reviews

A modern fifth wheel is showcased on a gravel site, featuring a sleek exterior with decorative accents. Sunlight illuminates the space, surrounded by lush greenery and tropical plants. The entryway is easily accessible, providing a glimpse of the outdoor setting in a relaxed atmosphere.

Camper/RV in Marathon

New 2/2 Fifth Wheels

The ultimate escape from the mainland to relax and reload while enjoying the comforts of home. Enjoy the sun and sea and at night relax at your new 35ft fifth wheel with all the amenities of home. Two bedrooms and two baths with a full modern kitchen. Reclining chairs and HD tv's. Great WIFI to stream your favorite shows or game. Great central air conditioning and modern appliances. BBQ grills on grounds and a beautiful beach for nightly sunsets.

A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.