Vacation rentals with a pool in Summerland Key

4.94 out of 5 average rating, 163 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 MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

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, 304 reviews

APRIL $Save $ Oceanfront 4 BIKES/2Kayaks. KING bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. At MM# 23 only 25min to Key West. In a gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C *Fully equipped kitchen *Includes grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library. Too much to list! WE WILL NEED YOUR EMAIL WHEN YOU CONFIRM THE BOOKING IN ORDER TO SEND YOU THE REGISTRATION FORMS AND THE RULE PACKET.

Top guest favorite

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.

4.9 out of 5 average rating, 61 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.

4.96 out of 5 average rating, 108 reviews

The living room features a light-colored couch and love seat, complemented by decorative pillows. A coffee table sits in the center, and a Smart TV is mounted on the wall. Natural light is provided by the sliding glass doors, leading to an outdoor space.

Cottage in Cudjoe Key

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

5 out of 5 average rating, 10 reviews

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

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 serene canal view during sunset, showcasing vibrant orange and pink hues reflecting off the water. A concrete dock extends into the water, equipped with a fish cleaning station. A table and chairs are positioned nearby for relaxation and enjoyment of the picturesque scene.

4.92 out of 5 average rating, 12 reviews

Blue Heaven Waterfront Home

Lobstering paradise 2 houses from open water, deep 60' canal, gorgeous water views, direct access to the Atlantic/Gulf, 35' dock/seawall. 3 zone mini split A/C and heat, overhead ceiling fans, fully stocked kitchen, microwave, washer/dryer, 42" Smart TV in living room and master bedroom, WIFI. King size bed in the master, queen bed in 2nd bedroom, and a queen sofa in the living room. Beach towels, linens. Marina store with bait & fuel onsite, 2 wide boat ramps, pool, hot tub & Rec center.

4.86 out of 5 average rating, 7 reviews

Tropical Paradise

Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.

4.95 out of 5 average rating, 80 reviews

Ocean~View w/ Dock, Pool, Kayaks, King Bed

Experience waterfront luxury in Venture Out on peaceful Cudjoe Key! Enjoy stunning Atlantic Ocean views, amazing sunsets, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Keep your boat at the house and reach the Atlantic or Gulf in minutes. Near Key West, this updated Keys getaway includes resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, especially lobster season in August, so book now!

5 out of 5 average rating, 21 reviews

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

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.

4.88 out of 5 average rating, 139 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 a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

4.84 out of 5 average rating, 118 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 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.

4.82 out of 5 average rating, 105 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.

Popular amenities for Summerland Key rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A light green house raised on stilts is depicted. Sturdy steps lead to the entrance on the right. A large, screened lanai offers views of the surroundings. The area is made accessible with ample parking on concrete and crushed stone surfaces.

4.81 out of 5 average rating, 62 reviews

Keys getaway

4.91 out of 5 average rating, 23 reviews

A serene pool area is surrounded by tropical plants and palm trees. Comfortable lounge chairs are positioned near the clear water of the pool. A shaded outdoor dining table with chairs sits on a wooden deck, enhancing the inviting atmosphere of this private space.

Home in Key West

Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools

5 out of 5 average rating, 10 reviews

Dolphin Daydreams at Venture Out

A vibrant green house is presented with large windows adorned with yellow shutters. A spacious front porch is bordered by tropical plants, while a gravel pathway leads to the entrance. Nearby, a blue trash bin is visible, along with a parked vehicle.

4.73 out of 5 average rating, 33 reviews

Tropical Island Getaway

A serene patio area showcases a private pool with illuminated edges, creating a calming ambiance. Outdoor furniture is arranged on a synthetic grass surface, framed by lush greenery and a tranquil water view, as the sky transitions to sunset hues in the background.

4.96 out of 5 average rating, 28 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

4.78 out of 5 average rating, 9 reviews

*NEW!*Paradise Point~VIEWS!~Open Water~Dock~Pool!

5 out of 5 average rating, 3 reviews

A Paradise Point by Sombrero Beach

Top guest favorite

A private backyard features a heated pool surrounded by tropical landscaping. Lounge chairs are positioned on the wooden deck beside the pool. The two-story home includes large glass doors that open onto the deck, providing easy access to outdoor spaces.

Home in Duck Key

5 out of 5 average rating, 101 reviews

Private Pool Tropical Oasis - Centrally Located

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.

4.9 out of 5 average rating, 165 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, 312 reviews

Affordable Beachfront Luxury Condo Sleeps 6

A bright and airy living space features a large sectional sofa, a dining area with a light-colored table and chairs, and large glass doors leading to a balcony with water views. Light wood paneling and artwork enhance the overall ambiance.

4.89 out of 5 average rating, 255 reviews

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

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.

4.95 out of 5 average rating, 190 reviews

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

4.92 out of 5 average rating, 124 reviews

Old Town Retreat • Pool • Walk to Duval •

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, 151 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

4.87 out of 5 average rating, 135 reviews

Moonlight Paradise Upgraded Family oasis Tropical

Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.

4.98 out of 5 average rating, 123 reviews

Gorgeous Ocean View in Paradise, Close to Key West

Other vacation rentals with a pool

A peaceful canal scene is presented with clear blue skies and palm trees lining the water's edge. The calm water reflects the greenery and nearby structures, creating a serene atmosphere. A patterned walkway runs alongside the canal, adding to the tranquil setting.

4.85 out of 5 average rating, 20 reviews

Chiquita Waterfront Canal Home

Top guest favorite

5 out of 5 average rating, 19 reviews

Waterfront 2-bedroom Home w/Pool and Spa

Tiny home in Big Pine Key

4.82 out of 5 average rating, 242 reviews

Tiny House | 35 min to KW + Free Parking & Pool

4.85 out of 5 average rating, 13 reviews

P78 - Charming 3 bedroom 2 bath home in Sombrero B

5 out of 5 average rating, 16 reviews

A bright and airy living area is filled with natural light from large windows offering expansive water views. A comfortable light blue sofa and a matching armchair provide seating. A decorative coffee table sits in the center, and tropical plants are visible outside.

Townhouse in Key West

Exceptional Water View With Boat Dock!

4.94 out of 5 average rating, 36 reviews

Home in Key West

Carysfort Reef Light Suite

4.81 out of 5 average rating, 26 reviews

Bungalow in Cudjoe Key

Oceanfront Bungalow Venture Out

A serene view of the canal is presented, featuring calm emerald waters under a clear blue sky. Surrounding structures include residences and docks. A boat is visible on the water, along with two boats secured to the dock, highlighting the tranquil coastal setting.