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Vacation rentals with a pool in Summerland Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Summerland Key

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

An outdoor space features a sparkling in-ground pool surrounded by a sun deck with several lounge chairs. A shaded screened-in porch is visible in the background, along with a gas grill and a cornhole game set nearby. Lush palm trees provide a tropical atmosphere.

Home in Marathon

4.99 out of 5 average rating, 144 reviews

Cancellation Deal; Sept 27 thru Oct 04; Save now!

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

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.

Home in Cudjoe Key

4.93 out of 5 average rating, 40 reviews

Rise And Shine On The Water

Spectacular sunrise view! Room to park one vehicle & 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., GRILL, 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.

Cottage in Cudjoe Key

4.93 out of 5 average rating, 135 reviews

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.

An aerial view showcases a spacious waterfront home surrounded by lush greenery and palm trees. A private heated pool is bordered by a white fence, with lounge chairs and umbrellas nearby. A boat dock extends into the water, enhancing the serene setting.

Home in Summerland Key

5 out of 5 average rating, 4 reviews

Waterfront Beach House with Dock & Heated Pool!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 200 foot dock for your boat. Exclusive heated pool to relax and enjoy the surrounding ocean view - just breath taking! The private lot is almost an acre with another home not rented separate (search for Barry Beach & Guesthouse for both homes). Stunning panoramic water views, sunrise, sunset, steps from ocean water. Bring or rent fishing and snorkel gear nearby to fish off the dock and enjoy the underwater scenery!

A three-story oceanfront home is showcased, featuring a spacious outdoor deck and private pool area. Lush palm trees surround the property, and a sandy pathway leads to the entrance. The home is painted in a light color, blending with the bright blue sky.

Home in Cudjoe Key

4.91 out of 5 average rating, 11 reviews

Latitudes-Ocean Front Pool

This tropical 6 bedroom 4 bath oceanfront home has a private heated salt water pool and huge outdoor living space. There is beach access, shared dock space and outdoor gazebo to watch sunsets. There is a 3rd story balcony that offers spectacular views of the sunrise and sunset. Bring up to a 24' boat or paddle out on one of the shared kayaks onsite. Fully equipped kitchen, linens, beach towels, a propane BBQ grill and 2 washer/dryers. This home is priced based on the number of guests.

An aerial view captures the oceanfront property showcasing lush greenery and inviting private beach access. Bright blue rooftops of the buildings contrast with the turquoise waters. Lounge areas with tiki huts and a heated pool are visible near the shore, promoting a relaxed outdoor atmosphere.

Condo in Key Colony Beach

4.93 out of 5 average rating, 246 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

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

4.86 out of 5 average rating, 107 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!

An aerial view captures the Venture Out Private Community at Cudjoe Key, highlighting a large swimming pool, sandy beach area, and surrounding palm trees. The clear blue water reflects the bright sky. Nearby homes and a calm bay are visible in the background.

Home in Cudjoe Key

4.86 out of 5 average rating, 103 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

A clear blue sky with scattered clouds is visible above the pool area. Palm trees line the edge of the space, providing a tropical feel. A rectangular pool and a smaller octagonal pool are present, surrounded by lounge chairs and an open expanse of sandy ground.

Home in Cudjoe Key

4.97 out of 5 average rating, 167 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.

Home in Cudjoe Key

4.81 out of 5 average rating, 275 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 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!

Home in Cudjoe Key

4.9 out of 5 average rating, 113 reviews

*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 covered outdoor dining area features a round table surrounded by six cushioned chairs. Scenic views of the turquoise water and distant shoreline are visible through the railing, with soft, natural light illuminating the space.

Bungalow in Cudjoe Key

4.86 out of 5 average rating, 14 reviews

Oceanfront Bungalow Venture Out

Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. 52' concrete dock/seawall complete with dock posts and fishing table. Lovely decor. Bocce ball, playground. Tennis, Hot Tub, 2 pools. Recreation center with billiards, darts, and ping pong. Post Office and a Library 24 Hour Gated Security. . 40" screened TV. WIFI Saturday to Saturday only 7 night minimum.

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Popular amenities for Summerland Key rentals with a pool

Free parking on premises

Air conditioning

House 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.

Home in Cudjoe Key

4.91 out of 5 average rating, 55 reviews

Keys Island Villa - Venture Out Home 354

Top guest favorite

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.

Home in Key Colony Beach

4.98 out of 5 average rating, 129 reviews

Paradise found!Key Colony Beach,Cabana Club.

Top guest favorite

An aerial view shows the property in proximity to the Atlantic Ocean, surrounded by palm trees. A dock extends into the clear water, with the colorful buildings of the surrounding area visible. The scene captures a serene coastal landscape, enhancing the appeal of a beachfront getaway.

Home in Key Colony Beach

5 out of 5 average rating, 7 reviews

Keys to Ohana. Ocean views. Private Pool, Hot Tub

Top guest favorite

A serene outdoor space features a private pool surrounded by stone decking. Two lounge chairs with blue cushions are positioned nearby, while a tiki hut adds a tropical touch. Lush palm trees and a canal lined with vegetation provide a tranquil backdrop.

Home in Marathon

4.98 out of 5 average rating, 63 reviews

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

Top guest favorite

Home in Key Colony Beach

4.95 out of 5 average rating, 123 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.

Home in Marathon

4.9 out of 5 average rating, 68 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

A private pool is surrounded by a lush tropical garden, featuring tall palm trees and vibrant foliage. The clear water of the pool reflects the sunlight, while stone pathways and colorful blooming plants enhance the natural ambiance.

Home in Marathon

4.94 out of 5 average rating, 65 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Top guest favorite

A serene outdoor pool is surrounded by lounge chairs and umbrellas, with palm trees swaying gently nearby. The expansive water reflects the clear blue sky, while the ocean can be seen in the background, enhancing the inviting atmosphere for relaxation.

Home in Key Colony Beach

4.98 out of 5 average rating, 112 reviews

Waterfront House with 37 ft Dock & Cabana Club

Condo rentals with a pool

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.

Condo in Key West

4.89 out of 5 average rating, 147 reviews

Tropical Escape at Sunrise

Top guest favorite

Aerial view of the condominium complex showcases a large pool surrounded by palm trees and lounge chairs, with direct access to a private beach. Calm turquoise waters extend beyond, and a wooden dock is visible in the distance under a clear blue sky.

Condo in Marathon

5 out of 5 average rating, 46 reviews

Beach Heaven-Private Beach, Pool

A scenic view of the waterfront reveals a calm harbor lined with boat slips. The vibrant blue water reflects the sky, while a tiki hut and chaise lounge chairs surround a heated pool in the foreground, enhancing the coastal ambiance.

Condo in Key West

4.87 out of 5 average rating, 215 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Top guest favorite

A large swimming pool is surrounded by palm trees and lounge chairs. Sun umbrellas provide shade near the water's edge. The inviting blue water reflects the clear sky above, contributing to a relaxing outdoor space ideal for leisure and socializing.

Condo in Key West

4.89 out of 5 average rating, 179 reviews

A Perfect Getaway

A spacious outdoor pool area is surrounded by lush greenery and palm trees. Lounge chairs are positioned around the pool, reflecting a serene atmosphere. A shaded gazebo offers a relaxing spot nearby, while the clear water invites refreshment under the bright sky.

Condo in Key West

4.95 out of 5 average rating, 163 reviews

Fully renovated 2/2 bath condo w/ shared pool!

Top guest favorite

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.

Condo in Marathon

4.96 out of 5 average rating, 107 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

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.

Condo in Islamorada

4.79 out of 5 average rating, 112 reviews

Studio with Balcony, Kitchen, Open Living Space

A clear pool glimmers under the sun, surrounded by palm trees. Lounge chairs are positioned by the poolside, while tiki huts can be seen in the distance. The condominium buildings frame the view, creating a peaceful outdoor space.

Condo in Key Colony Beach

4.86 out of 5 average rating, 132 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Other vacation rentals with a pool

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

5 out of 5 average rating, 42 reviews

Waterfront Escape -VACA-23-408

A serene view is presented from the pool area, featuring gentle waves lapping at the shore and numerous sailboats anchored in the harbor. Two palm trees provide shade, and a well-maintained lawn borders the pool, enhancing the coastal ambiance.

Home in Marathon

5 out of 5 average rating, 10 reviews

Sandbox

An aerial view reveals a modern house with a light blue exterior and a metal roof. A private pool is situated in the backyard, surrounded by lush greenery and lounge chairs. The property is enclosed with wooden fencing, providing a secluded outdoor space.

Home in Marathon

4.97 out of 5 average rating, 70 reviews

Sombrero beach oasis, great location, many amenities

A bright, elevated house with a coastal design sits amid lush palm trees under a clear blue sky. Vibrant green shutters contrast with the white exterior, while a spacious deck and railing are visible, inviting outdoor relaxation. The surrounding landscape features well-maintained shrubbery.

Home in Cudjoe Key

5 out of 5 average rating, 14 reviews

The Lookout #659 Venture Out - Gated Community

A waterfront view features a spacious canal lined with palm trees and houses. A private dock is visible with a boat moored alongside, offering easy access to the water. The serene, clear water reflects the blue sky and nearby structures.

Home in Cudjoe Key

5 out of 5 average rating, 4 reviews

Reel Keezy In Cudjoe Key #573

A sparkling swimming pool is surrounded by a white deck, with lounge chairs positioned on one side. Palm trees and greenery are visible in the background, providing a sense of tranquility and relaxation.

Tiny home in Big Pine Key

4.81 out of 5 average rating, 205 reviews

Cheerful Tiny House in the Florida Keys

A scenic waterfront view showcases calm turquoise waters surrounded by palm trees and residences. The image captures a bright blue sky, enhancing the serene atmosphere of the location. Visible is the adjacent dock area, providing direct access to the water.

Home in Cudjoe Key

4.9 out of 5 average rating, 20 reviews

Mermaid Magic at Venture Out

Home in Marathon

4.98 out of 5 average rating, 63 reviews

Casa Blue Flamingo

Quick stats about vacation rentals with a pool in Summerland Key

Total rentals
210 properties
Nightly prices starting at
R706 ZAR before taxes and fees
Total number of reviews
4.4K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace

Destinations to explore