Compare Vacation Rentals with Pools in Florida Keys, FL

Directly on the water in Cudjoe Key's secure Venture Out community, this apartment is just 20 minutes from Key West and 5 miles from the world-class Looe Key reef dive site.
This pet-friendly, family-friendly apartment with 2 bedrooms and 1 bathroom sleeps 6 and offers direct waterfront access with a seawall, a heated swimming pool, hot tub, kayaks, and bikes for exploring the Florida Keys.

Faro Blanco Resort, a Curio by Hilton, is located on Marathon's waterfront, a historic lighthouse landmark offering convenient access to attractions like The Turtle Hospital and Sombrero Beach.
This resort features four outdoor swimming pools and provides complimentary daily activities including sunset cruises and fishing trips, perfect for a getaway with a pool.

Located within the gated Kawama Yacht Club in Key Largo, this townhouse is just 0.2 miles from John Pennekamp Coral Reef State Park and steps from waterfront dining.
This family-friendly townhouse offers 1300 square feet of living space with 3 bedrooms accommodating up to 8 guests, featuring access to community amenities including tennis courts, a playground, BBQ areas, a sandy beach, and a swimming pool.

Directly in Key Colony Beach, this apartment offers exclusive access to the Cabana Club pool and private beach, just steps away.
This suite includes a sofa bed, accommodates two guests, and features a kitchen with a fridge, perfect for a beach and pool getaway with a swimming pool.

Oceanfront villas in Islamorada offer direct access to a private beach and a saltwater lagoon, located just 4.7 miles from John Pennekamp State Park and 4.8 miles from Dolphin Cove.
This recently renovated 2-bedroom, 2-bathroom villa provides 1100 square feet of living space with a balcony and ocean views, perfect for families seeking a getaway with a pool, complimentary WiFi, and proximity to local attractions.

Directly on a private sandy beach with ocean views, this first-floor Key Colony Beach apartment offers unparalleled access to the water and is located next to Sunset Park for nightly views.
This newly renovated apartment, perfect for two guests, features a fully equipped kitchen, a dedicated workspace with ocean views, and includes a heated swimming pool, beach loungers, and BBQ grills, all just a short drive from major Keys attractions.

Directly on the ocean in Tavernier, Florida Keys, this 2-bedroom apartment is located approximately 70 miles from Miami and 90 miles from Key West, providing immediate access to waterfront dining and marine activities.
Enjoy resort amenities including a private beach just a 5-minute walk away, a Jr. Olympic swimming pool with a hot tub, tennis, and pickleball courts, all within this gated community offering spectacular direct oceanfront views.

Directly on the beach in Marathon, Florida, Tranquility Bay Resort is a resort offering easy access to Crane Point Museums & Nature Center, just a 3-minute drive away, and Curry Hammock State Park, 13 miles away.
This resort features three swimming pools, including an adult-only and a heated children's pool, alongside water sports like kayaking and paddle boarding for a perfect pool getaway.

Enjoy a prime city center location in Key West, just 0.7 miles from Duval Street and a 17-minute walk to the Ernest Hemingway Home and Museum.
This 160 square feet house, ideal for two guests, features a refreshing swimming pool, a fully equipped kitchen, and air conditioning for your comfort.

Direct waterfront access with 35 feet of seawall and a swim ladder on Cudjoe Key offers exclusive entry to Venture Out's amenities, including a heated swimming pool and hot tub, just 20 miles south of Key West.
This 860 square feet apartment comfortably accommodates up to 6 guests, featuring 2 bedrooms, 2 bathrooms, a fully equipped kitchen, and complimentary bicycles and kayaks for exploring the Keys.

Located within Hawks Cay Resort in Duck Key, this recently remodeled townhouse is just 0.3 miles from Angler and Ale and the Dolphin Connection attraction.
This family-friendly house offers 900 square feet of living space with a private plunge pool, accommodating up to 4 guests with 2 bedrooms and 2 bathrooms, and features high-speed 1000mbps internet.

Waterfront resort Captain Pip's Marina & Hideaway in Marathon offers direct access to boating and is located just 0.9 miles from the Seven Mile Bridge and 4.3 miles from Sombrero Beach.
Enjoy aquatic adventures with on-site rentals and fishing, plus relax at the resort with a swimming pool, restaurant, and bar.

Just 500 feet from Islamorada's renowned fishing and water activities, this bungalow offers an excellent location for your Florida Keys getaway.
This 950 sq ft bungalow comfortably sleeps 4 guests and features a private patio, backyard, and access to a community heated pool, making it ideal for a pool getaway.

Direct oceanfront access in Tavernier offers stunning views of the protected mangrove forest and Atlantic Ocean, located within the Ocean Pointe Suites resort, 1.7 miles from the Wild Bird Center and 10 miles from John Pennekamp Coral Reef State Park.
This 910 square feet, family-friendly apartment with two bedrooms and two bathrooms accommodates up to six guests and features a renovated swimming pool, jacuzzi, and private lagoon beach, perfect for a pool getaway.

Directly on the private beachfront in Key Colony Beach, this apartment is a short walk or bike ride to rentals, a playground, and Sunset Park.
This family-friendly apartment with a pool sleeps four and features a fully equipped kitchen with stainless steel appliances, two bedrooms, and two bathrooms, perfect for a relaxing getaway.

Just 500 feet from direct beach access and marina, this apartment in Tavernier offers stunning ocean and conservation area views from its 3rd-floor location.
This family-friendly apartment, featuring 650 square feet, accommodates up to 4 guests and boasts a heated swimming pool, hot tub, and proximity to John Pennekamp Coral Reef State Park for an unforgettable pool getaway.

Experience waterfront living in Summerland Key with breathtaking ocean views, located just a 7-minute drive from the Florida Keys Beaches.
This family-friendly apartment offers 2 bedrooms, accommodates up to 5 guests, and features a swimming pool, hot tub, and a fully equipped kitchen for a perfect getaway with a pool.

This apartment is located by the scenic bay in Islamorada, Village of Islands, just a short walk from restaurants and shopping, and adjacent to Founders Park.
Enjoy this family-friendly apartment with 1400 square feet, featuring 4 bedrooms, 2 bathrooms, and sleeping arrangements for up to 10 guests, complete with a heated community swimming pool, private beach access, and two dedicated office areas perfect for remote work.

Directly on the Atlantic Ocean in Tavernier, Florida, at mile marker 92.5, this apartment offers a unique waterfront location within the Ocean Pointe resort, adjacent to protected mangrove nature preserves and approximately one hour from Miami.
This 1000 square foot apartment, accommodating up to 6 guests, features a full kitchen, air conditioning, and provides access to a junior Olympic-sized swimming pool, hot tub, and a private beach, perfect for a relaxing getaway with a pool.

Enjoy a private swimming pool and a fully fenced backyard in this 3-bedroom, 2-bathroom apartment, perfect for families and pet owners, located just under 10 minutes from Sombrero Beach in Marathon.
Explore Marathon with provided bikes and discover extensive outdoor living spaces including a Tiki bar and gas grill, all within an hour's drive of Key West and Dry Tortugas.

Directly on the ocean in Key Largo at mile marker 100, this oceanside villa is a short 500 feet walk to Dolphin Plus and close to John Pennekamp Coral Reef State Park.
This 1000 square foot, family-friendly house with a swimming pool accommodates up to 7 guests and features a private feel with direct access to a 40FT boat slip, kayaks, and bicycles for exploring the Keys.

Located in the tranquil Key Colony Beach neighborhood, this waterfront duplex is just a 5-minute walk to Glunz Beach Club and a 10-minute drive from the grocery store.
This spacious 1260 sq ft apartment offers 3 bedrooms and 2 bathrooms, sleeping up to 6 guests, and features a private swimming pool with a gas BBQ grill and outdoor dining area, perfect for enjoying the Florida Keys lifestyle.

Directly on the oceanfront in Key Largo, this brand-new teal-colored resort apartment offers direct ocean access and marina facilities, perfect for boating enthusiasts.
This pet-friendly apartment complex features a swimming pool and is conveniently located within the resort for a comfortable stay.

Located in Miami, Tucker at Palmer Dadeland is 3.3 miles from the University of Miami and 5.2 miles from Cocowalk Shopping Center.
This apartment offers an outdoor swimming pool, fitness center, and barbecue facilities for guests to enjoy.

Located in Summerland Key, this resort is 20 miles from Southernmost Point and Duval Street, with Key West International Airport 17 miles away.
This 400 square foot house offers a swimming pool, air conditioning, and internet, perfect for a getaway with pets allowed.

Enjoy open water views from this apartment in Summerland Key, just a short walk from the community pool, marina, and store.
This 800 square feet apartment offers 2 bedrooms, 1 bathroom, and accommodates up to 6 guests with a full kitchen, living area with a sleeper sofa, and a private BBQ grill, perfect for those seeking a getaway with a pool.

Just a 10-minute walk from Coco Plum Beach, this apartment in Marathon offers proximity to water activities, located 1.4 miles from A Deep Blue Dive Center.
This 400 sq ft apartment with a pool accommodates up to 7 guests, featuring air conditioning, a full kitchen with a dishwasher, and a terrace for enjoying the outdoors.

Enjoy direct bay and ocean access from this waterfront half-duplex in Key Colony Beach, located approximately 1.5 miles from Marathon Air Museum and Crane Point Museum and Nature Center.
This dog-friendly apartment features 2 bedrooms, sleeps 5 guests, and offers a private dock, kayaks, bicycles, and access to a shared swimming pool at the Cabana Club, perfect for a getaway with a pool.