Holiday rentals with a pool in Big Pine Key

4.95 out of 5 average rating, 370 reviews

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

4.94 out of 5 average rating, 151 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.

Apartment in Key Colony Beach

A spacious bedroom features a king bed with light bedding and decorative throw pillows. Large windows offer unobstructed ocean views and allow natural light to fill the room. A comfortable seating area is positioned nearby, facing the beach and tiki huts.

4.91 out of 5 average rating, 201 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Palm trees are seen swaying gently in the breeze, framing the entrance to the cottage, which features a welcoming front porch with two wooden chairs. The interior showcases a modern dining area, complete with a chandelier and decorative plants. A plunge pool is visible in the outdoor space, surrounded by tropical greenery.

4.93 out of 5 average rating, 104 reviews

Florida Keys Cottage with Pool - Hawks Cay Resort

Welcome to our tropical Conch Cottage, a lovely place to create memories on your idyllic Florida Keys vacation in paradise. Our stylish waterfront villa sits alongside a clear turquoise canal on picturesque Duck Key, inside the Hawk's Cay resort, and just 10 minutes from busy Marathon. Get involved in on-site activities like snorkeling, scuba diving, fishing, boating and dolphin encounters—or simply lay out on the coral stone patio, soak up the sun, and slide into your private plunge 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.

4.87 out of 5 average rating, 127 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!

4.9 out of 5 average rating, 443 reviews

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

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.

4.97 out of 5 average rating, 176 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.

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

4.81 out of 5 average rating, 292 reviews

Jan. Save $!$ Oceanfront 4 Bikes/2Kayaks. KING bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Apartment 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, 143 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.”

4.93 out of 5 average rating, 104 reviews

The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.

Apartment in Marathon

Canal View Condo w/ Pool, Balcony & Bar

Celebrate the season in paradise at THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, accommodating up to 4 guests. Featuring a complete kitchen, balcony, and access to resort amenities including a pool, Tiki Bar, restaurant, Marina, and more! Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

4.95 out of 5 average rating, 129 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.

4.89 out of 5 average rating, 113 reviews

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.

Villa in Marathon

Villa in Paradise. Plunge pool. Middle of the Keys

Baja Breeze 🏝, a freshly updated, family-friendly, resort-style villa in the ♥ of the Keys. ♥ Please save Baja Breeze by clicking on the heart in the top right hand corner, this will help you find it again and share with others! 🛶 Waterfront canal view 🌴 Gated Resort Area 👙 Private spa pool 📍 Halfway between Key Largo and Key West ☀️ Outdoor dining/lounge area 🍳 Fully stocked Kitchen 📶 300Mbps+ Wifi

Popular amenities for Big Pine Key rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An outdoor seating area features a thatched roof, providing shade over a collection of cushioned seating and a low coffee table. A swimming pool is visible in the background, surrounded by tropical greenery. Large glass doors lead into the interior of the home.

5 out of 5 average rating, 44 reviews

Discount Available! Pool 100' Dock, Fun Amenities!

4.88 out of 5 average rating, 121 reviews

A serene pool area is surrounded by lush tropical palm trees and vibrant landscaping. Sunlight reflects off the clear water, creating a calming ambiance. Nearby, a white lounge chair is positioned for relaxation, with a life preserver visible on the side.

Home in Key West

Gone Coastal

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

4.99 out of 5 average rating, 156 reviews

Sea Ray Cove w/ Pool, Beach, 80' Dock & Tiki hut

4.95 out of 5 average rating, 140 reviews

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

A well-lit dining area features a round wooden table surrounded by six woven chairs. A decorative centerpiece is placed on the table. Adjacent, a cozy living space is visible, showcasing a sectional sofa, a ceiling fan, and large windows allowing natural light.

4.86 out of 5 average rating, 69 reviews

Cozy 2 br/2 bath home in Cudjoe

4.95 out of 5 average rating, 132 reviews

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

Home in Key Colony Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

5 out of 5 average rating, 3 reviews

Home in Little Torch Key

Conch House -Ocean front -Dock

A spacious outdoor area features a tiki hut with a thatched roof, a swimming pool surrounded by lounge chairs, and a boat docked beside a canal. Lush palm trees provide shade, enhancing the tropical ambiance of the property. The home is visible in the background.

4.96 out of 5 average rating, 79 reviews

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Apartment rentals with a pool

A serene waterfront view reveals gentle waves lapping against a sandy shoreline. Beach chairs are arranged near the water, providing a relaxing spot to enjoy the scenery. Lush palm trees frame the tranquil setting, enhancing the sense of peacefulness.

4.95 out of 5 average rating, 42 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

4.9 out of 5 average rating, 154 reviews

Tropical Escape at Sunrise

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, 302 reviews

Affordable Beachfront Luxury Condo Sleeps 6

A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.

4.91 out of 5 average rating, 236 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

4.96 out of 5 average rating, 113 reviews

A light-filled living area is visible, featuring a comfortable seating arrangement and a mounted television. A dining table occupies the foreground, adorned with a bowl of oranges. The walls are painted in soft blue, providing a relaxed atmosphere, with a ceiling fan overhead.

Apartment in Marathon

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

4.79 out of 5 average rating, 120 reviews

An aerial view displays a resort setting featuring a heated pool surrounded by palm trees, beach cabanas, and lounge chairs. The property extends towards the beach, with picnic tables and a landscaped area visible. The ocean borders the scene, enhancing the tropical atmosphere.

Apartment in Islamorada

Sandy Toes Approved — Studio Beach Escape

4.91 out of 5 average rating, 114 reviews

Vacation home Island Suite 16

4.96 out of 5 average rating, 28 reviews

An aerial view showcases the beachfront location of the condominiums, with a gleaming pool surrounded by well-kept lawns. White sandy beaches meet the clear turquoise waters, while tropical palm trees sway gently in the breeze. Nearby canals and homes create a serene coastal community.

Apartment in Marathon

*NEW* Private Beach, pool & fully loaded kitchen

Other holiday rentals with a pool

A two-story waterfront home is situated under a clear blue sky, surrounded by palm trees and lush greenery. The property features a bright white exterior with a balcony, along with a manicured yard of decorative rocks and native plants.

4.92 out of 5 average rating, 62 reviews

Keys Island Villa - Venture Out Home 354

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, 57 reviews

Marathon Keys Escape • Pool • Hot Tub • Near Beach

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.

5 out of 5 average rating, 21 reviews

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

5 out of 5 average rating, 6 reviews

Dolphin Daydreams at Venture Out

4.85 out of 5 average rating, 47 reviews

A private pool glistens under the sun, surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. In the background, a tiki palapa with a thatched roof offers shaded seating, complemented by lush tropical foliage and a distant pink house.

Home in Summerland Key

Pelico Palms Sunset Suites

Campervan/Motorhome in Big Pine Key

The exterior of the RV is set against a backdrop of lush palm trees and tropical foliage. Decorative elements, including colorful painted shells and a seahorse, adorn wooden fences. Potted plants add greenery, complementing the sandy ground.

4.74 out of 5 average rating, 23 reviews

Island Girl Big Pine Key

5 out of 5 average rating, 19 reviews

An open-concept living area features wraparound seating in dark leather surrounding a polished wooden dining table. Abundant natural light filters through panoramic windows, reflecting off the rich wooden flooring. Tropical-themed wall decor and greenery enhance the inviting aesthetic. A well-equipped kitchen is visible in the background.

Boat in Key West

Sailboat Stay + Resort Amenities