Holiday rentals with outdoor seating in Monroe County

4.98 out of 5 average rating, 230 reviews

A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.

Home in Key Largo

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

4.9 out of 5 average rating, 223 reviews

A wraparound balcony offers panoramic views of Biscayne Bay and the Miami skyline. The scenic vista is complemented by lush greenery below and various buildings in the foreground. The sky is bright with scattered clouds, enhancing the sense of openness and tranquility.

Flat in Miami

Stunning Studio w/Bay & City View Free Park/Pool

INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! in Coconut Grove, this privately owned & renovated deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

4.99 out of 5 average rating, 111 reviews

Guest house in Miami

Casa Palma Guesthouse with Private Patio & Garden

Make your Miami stay peaceful and memorable at Casa Palma, a centrally located guesthouse minutes away from the best of Miami! Great restaurants, wine shop and a supermarket in walking distance. Free and very close-by Coral Way trolley line takes you to Coral Gables, Brickell, downtown and Port of Miami cruise hub. Close drives to Little Havana, Coconut Grove, Coral Gables & Brickell. Easy 15-20 minute drives to Miami International Airport, Wynwood, South Beach or lovely Key Biscayne beaches.

A spacious bedroom features a comfortable bed with a light-colored quilt, complemented by wooden accents. Natural light filters through, illuminating the room's earthy tones. A small nightstand and artwork depicting a bird add character, while a private bathroom entrance is visible in the background.

4.89 out of 5 average rating, 245 reviews

Quiet Guest Suite, Private Entrance, Patio+Parking

Take it easy at this unique and tranquil getaway in our 1930's Spanish Villa in the center of Little Havana and Coral Gables in the heart of Shenandoah. Your Guest Suite is equipped with a private entrance, private garden, and parking. Casita Amorcita is designed to give you the feeling of 'home' and 'love,' with the guest experience in mind. All linens are 100% cotton. Here you will have all that you need to rest, recover, recharge, and enjoy. We look forward to welcoming you home.

A spacious driveway curves past vibrant tropical plants and palm trees leading to a welcoming entrance of the property. The house features a warm orange exterior with decorative elements and a large garage door, complementing the lush landscaping.

4.9 out of 5 average rating, 390 reviews

Guest Suite-Exterior Entrance, SelfCheckin.

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place for you. We are conveniently located between Key Largo and Downtown Miami, in an upscale community. You’ll feel safe and welcome here! -GATEWAY to the Keys and Everglades -Private entrance -Self Check-in -Free Parking -Fast WIFI -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

Apartment in Key Colony Beach

A bright and airy studio room features two queen-sized beds with crisp white bedding and anchor-themed decorative pillows. Light blue accents are present throughout, complemented by coastal artwork on the walls. Large windows allow natural light to fill the space, enhancing its serene atmosphere.

4.92 out of 5 average rating, 333 reviews

Coastal Key Colony Beach Condo, Oceanfront Complex

Lovely coastal Keys studio condo in Key Colony Beach oceanfront complex with heated pool and private beach. Unit #17 has new beds with memory foam mattress toppers and renovated kitchen with granite countertops stocked with everything needed to cook a complete meal (dishes, cookware, appliances and of course blender, 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.

A welcoming entrance is highlighted by two chairs positioned on a patterned rug. Potted plants are arranged around the space, accompanied by a decorative light fixture. A ceiling fan is visible above, and a door leads into the private room, creating an inviting atmosphere.

4.96 out of 5 average rating, 142 reviews

Adorable private studio

Relaxing, private, peaceful and centrally-located studio. You do not share your space with anyone. Walking distance to restaurants, supermarket, bus stop, Gym and Florida International University. Conveniently close to Miami Airport, Kendall Regional Hospital, Dolphin Mall, TopGolf, Everglades Airboat Expeditions, City Place Doral with Fresh Market, shops, Movie Theaters, Comedy Club, live music and more. Eleven miles from Bayside and Wynwood Walls. The beach? A short 15-mile drive!

4.82 out of 5 average rating, 264 reviews

Private Guest Suite

Beautiful lake view GUEST SUITE. It includes a private bedroom with private bathroom & entrance. The room sleeps up to 4 guests in a bunk bed consisting of 2 twin beds and a full size bed on the lower level. Room has a TV, mini-fridge, & access to an outdoor area to enjoy the great lake view. There is an additional $20 per person per night fee for more than 2 guests. Note: there is no kitchen access therefore no cooking on premises. Miami Beach = 26 miles Miami Airport = 19 miles

4.93 out of 5 average rating, 372 reviews

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

4.94 out of 5 average rating, 159 reviews

A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.

Houseboat in Key West

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

4.96 out of 5 average rating, 127 reviews

Tiny home in Miami

Private Gated VERY Tiny House • Coconut Grove

Quiet, respectful solo guests only. Owner onsite. No visitors. ULTRA small Tiny House (10x10) in walkable Coconut Grove with AC, fast WiFi, tiny kitchen, fridge & private outdoor shower. Gated, peaceful setting near cafés, parks, bayfront paths & the Village. Eco-focused urban glamping in Miami for minimal luggage, early nights & guests who value calm, safety, nature & a no-TV, no-frills stay.

A cozy living area is featured with a light gray sofa positioned beside a circular coffee table. An accent wall displays a decorative sign, while shelves are neatly arranged with books and decorative items. A soft glow is provided by a floor lamp in the corner.