
Holiday 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.

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.

Oceanfront Sunrise Condo Private Beach Heated Pool
Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Movie Theater | HotTub | Pool | Boat/RV/EV Parking
Welcome to Paradise Palms: ⭑ 1750 sqft liveable space on 10,500 sqft estate ⭑ Private home, deck, patio & backyard, overlooking a beautiful scenic landscape ⭑ Crystal pool, hot tub, movie theater, remote workspace, game room with arcade & more ⭑ Secure parking for up to six vehicles, boat trailer parking, RV and EV charging ⭑ 10 min to sombrero beach & just minutes to all island attractions ⭑ Fully stocked kitchen ⭑ Extremely safe neighborhood License #VACA-24-20 License #VACA-24-32

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.

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.

The Roseate House at Grassy Key
Make The Roseate House at Grassy Key your next get away. Relax, fish, swim and explore at your own personal resort. The home is perfect for couples, family or girls retreat. Families return year after year to create their memories. Honeymooners appreciate the privacy as well as the attention to detail. Come live among the treetops in this vintage conch Key West style cottage situated half way between Key Largo and Key West.

Florida Keys Resort-Style Home w/ Pool & Dock 5/3
Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!
Popular amenities for Vaca Key rentals with a pool
House rentals with a pool

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

Yellowtail Getaway with Boat Dock and Pool 2

Oceanfront with Pool near Sombrero Beach

*New Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes

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

Waterfront House with 37 ft Dock & Cabana Club

Beach Front

Emerald Oasis ~ Lux Waterfront Gem ~ Heated Pool ~
Apartment rentals with a pool

Reel Hip– Heated Pool, Boat Slip, Heat, King Bed

Oceanside Spacious Studio Escape

Luxury condo with boat slip overlooking the bay

Private Beach in Marathons Key Colony Beach

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Paradise found! Sea-Esta Condo beach and pool.

Studio with Balcony, Kitchen, Open Living Space

Carney's Reef 1B/1B Pool, Large Patio &Living Room
Other holiday rentals with a pool

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

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

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

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

Spacious lux home, private pool/spa, 80' dock

Serenity Oasis~Pool!~Kayaks~Grill~Bikes~Spa

Private Pool! Luxury Paradise Pointe, Pet Friendly
Destinations to explore
- Seminole Holiday rentals
- Miami Holiday rentals
- Central Florida Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Fitness-friendly rentals Vaca Key
- Villa rentals Vaca Key
- Rentals with a hot tub Vaca Key
- Flat rentals Vaca Key
- Rentals with a washing machine and dryer Vaca Key
- Family-friendly rentals Vaca Key
- Townhouse rentals Vaca Key
- Rentals with a fireplace Vaca Key
- Rentals with outdoor seating Vaca Key
- Rentals with a kayak Vaca Key
- Rentals with lake access Vaca Key
- House rentals Vaca Key
- Waterfront rentals Vaca Key
- Apartment rentals Vaca Key
- Rentals with breakfast Vaca Key
- Rentals with a firepit Vaca Key
- Pet-friendly rentals Vaca Key
- Rentals with beach access Vaca Key
- Rentals with a patio Vaca Key
- Rentals with an accessible-height toilet Vaca Key
- Beachfront rentals Vaca Key
- Rentals with pools Monroe County
- Rentals with pools Florida
- Rentals with pools United States
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Cannon Beach
- Calusa Beach & Loggerhead Beach
- Cocoa Plum Beach
- Theater of the Sea
- Conch Key
- Far Beach
- Sea Oats Beach
- Horseshoe Beach
- Long Key State Park
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Bahia Honda State Park
- Keys' Meads
- Sandspur Beach
- Long Beach