Holiday rentals in Spanish Harbor Key

4.89 out of 5 average rating, 177 reviews

An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

Cottage in Cudjoe Key

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

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5.0 out of 5 average rating, 47 reviews

Oceanfront Cottage with Open Water Views

Oceanview Serenity provides stunning open water views, and a 60 foot seawall for your boat. Comes with paddle board, kayaks, and more. Newly renovated 2BR cottage sleeps MAXIMUM OF FOUR (4) GUESTS, with a King in the Master BR and one Queen size bed Guest BR (both with new JW Marriott mattresses for comfort). All new appliances! Enjoy resort amenities like a pool, hot tub, tennis, and marina store. Just 30 minutes from Key West. One-time $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON

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Tiny home in Big Pine Key

A serene beach scene captures soft sands meeting clear waters under a bright blue sky. Lush palm trees frame the view, while visitors are seen enjoying the tranquil coastline and gentle waves. Green foliage and distant beach cabanas are also visible, enhancing the natural beauty.

4.88 out of 5 average rating, 130 reviews

Cottage 30 min from Key West, free parking, pool

Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

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4.77 out of 5 average rating, 147 reviews

Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.

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5.0 out of 5 average rating, 16 reviews

Home in Marathon

Luxury Waterfront Home - Marathon, FL Keys - 5BR

Welcome to Seven Sunsets – a waterfront retreat in Marathon’s brand-new Emerald Flats community, offering stunning ocean views and the iconic Seven Mile Bridge. With glowing sunset backdrops, marina views, and dockage for up to a 40’ boat, this five-bedroom home is perfect for families, boaters, and sunset lovers. Enjoy a small beach area with paddle boards, spacious indoor-outdoor living, and amenities like a fully stocked kitchen, in-home laundry, outdoor games, and pet-friendly policies.

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Cottage in Little Torch Key

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

4.89 out of 5 average rating, 184 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

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4.94 out of 5 average rating, 36 reviews

Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!

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5.0 out of 5 average rating, 4 reviews

Home in Marathon

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

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An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

4.96 out of 5 average rating, 208 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

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A spacious outdoor dining area features a glass-top table with several red chairs, set against a vibrant backdrop of greenery and water. The view of the calm sea and fluffy clouds can be seen in the distance, enhancing the tranquil setting.

4.88 out of 5 average rating, 42 reviews

Yellow Home - Receive $400 towards a Boat Rental!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our homes staying between the dates of Sept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026 Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home. Kayaks included. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

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A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

4.83 out of 5 average rating, 111 reviews

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

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