Vacation rentals with beach access in Big Pine Key

4.94 out of 5 average rating, 140 reviews

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

Cottage in Cudjoe Key

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

4.96 out of 5 average rating, 114 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Condo in Key Colony Beach

A spacious bed is adorned with crisp white linens and a vibrant throw pillow featuring a fish design. Large windows frame the room, allowing natural light to illuminate the interior while offering views of the ocean and nearby palm trees.

4.96 out of 5 average rating, 220 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

A backyard area features white sand, surrounding palm trees, and a tall American flag. The A-frame house is visible in the background, complemented by a wooden dock leading to the water. Lounge chairs are arranged neatly, enhancing the outdoor space's appeal.

4.99 out of 5 average rating, 108 reviews

ABeachBungalow-60’dock w/ access to pool and beach

"A Beach Bungalow" A-frame has everything you need for a relaxing vacation. 2 bedroom, 2 bath Key Colony Beach rental home with easy ocean access. Fully equipped kitchen with all new appliances. Living room with dining area, flat screen tv, wifi, cable, bbq and beautiful views of the water. Master bedroom with king bed and bathroom with large shower. 2nd bedroom (loft) with 2 twin beds and closet. Tackle room to store gear with extra refrigerator. Boat trailer parking on site.

4.87 out of 5 average rating, 115 reviews

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.

Home in Cudjoe Key

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!

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

4.97 out of 5 average rating, 107 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

Condo in Key Colony Beach

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

4.87 out of 5 average rating, 135 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

4.92 out of 5 average rating, 170 reviews

A serene pool area features a clear blue water swimming pool surrounded by lounge chairs and umbrellas. A lush landscape of palm trees and green foliage complements the setting, with a charming cottage visible in the background.

Townhouse in Key West

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat 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, kayaks, paddle boards and golf carts can be rented locally

4.91 out of 5 average rating, 116 reviews

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.

Home in Cudjoe Key

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.

4.95 out of 5 average rating, 110 reviews

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

A vibrant sunset paints the sky in shades of orange and pink, reflecting off the tranquil canal water. Palm trees frame the scene, while nearby boats are anchored along the dock. The peaceful ambiance captures the essence of coastal living in Key Colony Beach.

4.98 out of 5 average rating, 130 reviews

Paradise found!Key Colony Beach,Cabana Club.

Second Wind is on the 9th Street canal, a beautiful corner lot with exceptional views and ocean breezes. Cabana Club! Dockage for a 20 ft boat. A two-minute walk to Sunset Park in the wonderful community of Key Colony Beach! Open floor plan with cathedral ceiling, large deck with seating for six overlooking the pristine turquoise canal. It is the perfect place for your Florida Keys getaway!

4.95 out of 5 average rating, 128 reviews

A pathway is lined with thatched roofing, leading toward a cozy cottage illuminated by soft light. The wooden dock extends over calm waters, framed by lush greenery. Subtle, colored lighting enhances the natural textures of the setting, creating a serene atmosphere.

Cabin in Marathon

Conch Key Cottages with SailboatorBoatslip incuded

We are located on Conch Key in the Florida Keys. We have a two bedroom traditional Conch house on the water boat slip included. Exclusive use of a Com-Pac, 23 foot sailboat, kayaks and bicycles. Note use of sailboat if qualified and after initial orientation and check out. Please verify potential use of sailboat prior to reservation

Popular amenities for Big Pine Key beach access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.83 out of 5 average rating, 18 reviews

An aerial view of the beachfront condo building is captured, revealing its three stories and proximity to the ocean. Surrounding palm trees enhance the tropical ambiance, while the serene blue water reflects sunlight. A small parking area is visible in front of the property.

Apartment in Marathon

Seaside Villa~ Charming Beachfront Condo w/ Pool!

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

4.9 out of 5 average rating, 152 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

A warm-toned room features wood-paneled walls accented by natural light from two windows. A spacious bed with an orange bedspread is positioned alongside a cozy seating area comprising two cream-colored couches facing a small round table.

4.84 out of 5 average rating, 824 reviews

Duval Balcony - Street Suite

A decorative wooden sign is mounted on a white post, featuring the text 'Center Court Historic Inn & Cottages' in bold letters. Lush tropical greenery surrounds the area, with palm trees and vibrant plants visible, creating a welcoming entrance to the property.

4.95 out of 5 average rating, 337 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

Apartment in Key Colony Beach

The room features two spacious beds with light-colored bedding, complemented by decorative pillows. A ceiling fan is present above, while large windows with shutters allow natural light. Colorful artwork depicting flamingos adorns the walls beside bedside tables and lamps.

5 out of 5 average rating, 9 reviews

2 Bdrm Oceanfront Complex Private Beach & Pool

A private balcony features a round table surrounded by four chairs, providing a comfortable space to enjoy the ocean view. Lush greenery and palm trees are visible in the background, with the tranquil ocean further enhancing the outdoor setting.

5 out of 5 average rating, 3 reviews

Oceanview condo w/pool, jacuzzi

4.97 out of 5 average rating, 108 reviews

A light-filled living room features a blue sofa, a comfortable chair, and a glass coffee table. Large sliding doors open to a balcony with ocean views. A soft area rug lies on the tiled floor, adding warmth to the space, while sunlight illuminates the room.

Apartment in Marathon

Beachfront Condo w/ Ocean Views in Marathon

The modern building is designed with balconies overlooking a serene pool area. A turquoise pool is bordered by lounge chairs and palm trees, creating a refreshing outdoor space. The backdrop features a clear sky and a sandy waterfront, enhancing the tranquil ambiance.

4.91 out of 5 average rating, 34 reviews

Oceanfront Condo in Key West, FL

House rentals with beach access

5 out of 5 average rating, 7 reviews

KCB Tropical Escape

5 out of 5 average rating, 18 reviews

Two pelicans are perched on a wooden dock, surrounded by rippling water. The dock is supported by green posts, providing a serene setting in a tropical landscape. Subtle foliage in the foreground enhances the natural ambiance of the scene.

Home in Cudjoe Key

Oceanside home 111, dock,kayaks,bikes,pool,fishing

The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.

4.91 out of 5 average rating, 182 reviews

Beachfront Villa - Florida Keys

A light-filled living area features a comfortable seating arrangement with leather sofas and a large area rug. A television is housed within a white entertainment unit, flanked by decorative glass vases. Expansive sliding glass doors open to the outside, providing an airy ambiance.

4.95 out of 5 average rating, 58 reviews

Sea Glass Beach Bungalow in Key Colony Beach!

An aerial view captures the waterfront property with a heated pool and outdoor seating areas, surrounded by lush palm trees. The private canal is visible, along with neighboring homes. Blue skies enhance the tropical setting, creating a serene atmosphere perfect for relaxation.

4.9 out of 5 average rating, 10 reviews

Grand Blue/Dock/HtdPool/PoolTable/GameRoom/MinGolf

The waterfront patio features a wooden dock leading into the calm water, surrounded by neatly arranged lounge chairs and palm trees. The single-story home is seen in the background with large glass doors and windows, allowing for ample natural light.

5 out of 5 average rating, 31 reviews

Boat Dock+King Beds & Cabana Club

A comfortable brown leather sofa is adorned with striped decorative cushions and a prominent 'love home' pillow. A wooden coffee table holds various brochures and a remote. In the background, fishing rods are visible, and a neutral-colored wall adds to the relaxed atmosphere.

4.89 out of 5 average rating, 28 reviews

Pet Friendly Half-Duplex Cottage w/40' Slip Option

A private pool is bordered by lush palm trees and a thatched Tiki Hut. Lounge chairs are arranged around the pool area, and colorful outdoor decor adds a cheerful touch. Clear blue skies and sunshine illuminate the space, creating an inviting outdoor retreat.

4.92 out of 5 average rating, 24 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

Condo rentals with beach access

4.88 out of 5 average rating, 109 reviews

A row of townhomes is positioned along the water's edge, surrounded by well-maintained landscaping. Lush green trees provide shade, and the calm water reflects the serene environment. The horizon reveals a glimpse of distant trees and open water.

Condo in Duck Key

Villa 5027 on Duck Key BOAT SLIP available

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 300 reviews

Affordable Beachfront Luxury Condo Sleeps 6

A living room is presented with a combination of modern and inviting elements. A flat-screen TV is mounted on the wall, complemented by two seating areas featuring comfortable sofas and chairs. Natural light filters through the balcony doors, enhancing the space's brightness.

4.99 out of 5 average rating, 75 reviews

The Palms

Condo in Key Colony Beach

An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.

5 out of 5 average rating, 20 reviews

Private Beach in Marathons Key Colony Beach

A charming two-story building with light pastel-colored siding and white railings is shown. The entrance features a circular window and a welcoming porch with comfortable seating. Lush greenery and a white picket fence frame the entrance, enhancing the inviting exterior.

4.9 out of 5 average rating, 182 reviews

A Perfect Getaway

A spacious balcony is furnished with a dining table and chairs, offering views of the ocean and nature preserve. Lounge chairs provide a comfortable space for relaxation, while vibrant table settings enhance the inviting atmosphere. The sky reflects soft colors of sunset, creating a serene backdrop.

4.89 out of 5 average rating, 18 reviews

Atlantic Reflections at The Beach

A clear, inviting outdoor pool is surrounded by lush tropical landscaping. Palm trees are scattered around, softening the edges of the pool area. A multi-story building with a light-colored exterior provides a backdrop, featuring several balconies with white railings.

5 out of 5 average rating, 9 reviews

Hyatt Beach House-Quiet Key West Spot!

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.