
Vacation rentals with a pool in Vaca Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Vaca Key
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Sea Ray Cove; Pool, 75’ Dock and steps to Beach
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.

Beautiful Waterfront book now Thanksgiving is Open
This property is like having your own private resort. We are on the Gulf of Mexico with a Million-dollar waterfront view & sunsets. 4BR + bonus room w/queen bed & futon. 2 full bathrooms 4 TVs. Pool, Private Dock. Watch the Dolphins daily. We a located next to the World-Famous Dolphin Research Center. House has wrapped around deck plenty of seating inside/out. Large private yard with plenty of room for all your needs. Walking distance to restaurant, marina. Kayaks/Paddleboards mostly available.

Boater’s Paradise 3br/2.5ba at Coral Lagoon
*PLEASE NOTE* Villa slips/canal are under construction until Dec 2025. Please inquire before booking. Spectacular PET FRIENDLY 3 bed/2.5 bath 1350sf villa in beautiful Coral Lagoon, complete with a 40 foot wet slip and all the amenities! Spread out and enjoy the spacious, clean interior with free high speed wifi. Step outside to your boat and enjoy all the Gulf and Atlantic have to offer - both easily accessible in minutes. Relax with a drink at the pool after a long day of fun in the sun.

Coastal Key Colony Beach Condo, Oceanfront Complex
Lovely coastal Keys studio condo in Key Colony Beach oceanfront complex with heated pool and private beach. Unit #17 has new beds with memory foam mattress toppers and renovated kitchen with granite countertops stocked with everything needed to cook a complete meal (dishes, cookware, appliances and of course blender, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Angler’s Eden
Amazing get-away in the beautiful Florida Keys! This property (constructed in 2018) is a haven for families seeking to escape to paradise year-round. Situated on a deep water canal with ocean access and enough dock space to park your boat for the week. A floating dock is also provided with kayaks and a paddle-board. Enjoy the large pool or ping pong table, or lounging in the sun! Beautiful Sombrero Beach is within walking distance (approx 1.5 miles) via a paved bike path.

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!

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa
***A quick update regarding the property. The community has scheduled construction to begin on the seawall in our backyard. At this time, work has not yet started, but a temporary fence has been placed at the back of the property for safety. The view from the home is still beautiful, and we do not currently know the exact start date for construction or if/when there may be any noise. We will keep you informed of any changes as soon as we learn more.

Anglers Terrace, Condé Nast Traveler's Best Airbnb
As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

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!

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.

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 Vaca Key rentals with a pool
House rentals with a pool

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

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

Sunset Views, Pool and Dock

Oceanfront with Pool near Sombrero Beach

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

“La casa azul” step 3’ to a private pool

Beach Front
Condo rentals with a pool

Your Happy Place - Oceanfront

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Condo in the Keys, Peaceful ocean view retreat!

Ocean views at “Sangria Sunrise” 10% off Charters

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Studio with Balcony, Kitchen, Open Living Space
Other vacation rentals with a pool

Oasis Canal-Front Home: Pool, Dock, BBQ, and more!

Oceanfront Getaway in Marathon!

Yellowtail Getaway with Boat Dock and Pool 2

Ocean Escape 97

Newely Renovated 3/2-private pool/dock/cabana club

Casa Blue Flamingo

Salt&Seaglass. Key Colony. Screen Porch. Pool Club

2-story condo w/ panoramic bay views and balconies
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
- Cannon Beach
- Conch Key
- Theater of the Sea
- Far Beach
- Sea Oats Beach
- Long Key State Park
- Horseshoe Beach
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Sandspur Beach
- Bahia Honda State Park
- Long Beach
- Keys' Meads