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

Key Colony Beach Luxury Condo, New Modern Interior
Private studio condo at Key Colony Beach with a private balcony, heated pool and sandy beach. Unit #15 was recently renovated and offers one comfy King size bed and a fully equipped kitchen with essentials (stove, oven, toaster, microwave, blender, fridge, cooking utensils). Wifi, Amazon Echo and a TV. Enjoy a short walk to Sunset Park next door to experience a stunning Florida Keys sunset. Guests also have access to a private beach with lounge chairs, patio tabales, tiki huts, and BBQ grills.

Fully renovated 2/2 bath condo w/ shared pool!
**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

Quiet tropical Oasis setting with 1 bed and 1 bath
Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

Escape to the Seaside - Tiburon Cottage
Our one bedroom suite features separate bedroom and living areas, giving you the space and comfort to relax, sleep and eat. Set yourself up in a large in-suite space with private entrance. The suite provides all the comforts of home. Unpack and stretch out in a stylish suite with a sofa, flat screen TV, complimentary Wi-Fi and premium cable programming or explore all the Keys have to offer. Here, you’ll have everything you need, because to us it’s not a temporary accommodation, it’s your home.

Guest Suite-Exterior Entrance, SelfCheckin.
If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place for you. We are conveniently located between Key Largo and Downtown Miami, in an upscale community. You’ll feel safe and welcome here! -GATEWAY to the Keys and Everglades -Private entrance -Self Check-in -Free Parking -Fast WIFI -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

Condo in Brickell Business District
Stunning one bedroom condo located in the best area of Brickell just minutes away from Brickell City Centre and Mary Brickell Village with restaurants, bars, shops and entertainment. About this Space -Approx.818 sqft of natural light filled space with gorgeous bay and city views and a large private balcony with dining table and large patio couch -High-speed Wi-Fi -1 free assigned parking spot -Pool, hot tub, jacuzzi, steam room, game room, state of the art gym, and business center

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

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!

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
Enjoy a Tavernier adventure on a private 60-acre oceanfront sanctuary. The condo was recently renovated & is beautifully designed with comfortable, beach chic decor. It offers an abundance of natural light surrounded by windows overlooking lush landscaping and the Atlantic Ocean. Ocean Pointe Suites offers a private sandy beach, a junior Olympic sized pool, a 14-person spa, a boardwalk, a pickleball court, deep-water marina, gazebo, 2 tennis courts & more!

“Have Fun at Hacienda Paraíso” Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

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.
Popular amenities for Monroe County rentals with a pool
House rentals with a pool

Tiny Home on Waterfront | Bay Views | Deck | Pool

Sea Ray Cove w/ Pool, Beach, 80' Dock & Tiki hut

The Paradise 2

Waterfront Home 37.5-ft dock, Cabana Club Included

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

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ

Beautiful open plan remodeled home in Key Colony

Sanctuary Salt water heated pool BBQ Grill Oasis
Apartment rentals with a pool

Luxury Top Floor Suite W/ Unobstructed Ocean View

Luxury PH at Brickell Bay-Amazing MIAMI City VIEWS

Modern Luxe at Brickell | Pool & Spa Access

Front Facing Top Floor Penthouse with Ocean Views

Ocean Views at Ocean Pointe

Stunning 2 bedroom+17 foot ceilings & heated pool

Vacation home Island Suite 16

Sky High Penthouse! Water & City Views (top floor)
Other holiday rentals with a pool

43 Floor Miami 1BD Near Arena

Ocean front 1BR/1BA Suite w/ kitchen & living rm

NEW | Luxe 1BR, District 225 | Pool & Great Views

Beach Heaven-Private Beach, Pool

Modern 1BD Penthouse with Stunning Bay View

*Free Parking* TOP FLOOR Condo

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

Bohemian Beach Bungalow
Destinations to explore
- Rentals with a sauna Monroe County
- Hotel rooms Monroe County
- House rentals Monroe County
- Hostel rentals Monroe County
- Apartment rentals Monroe County
- Smoking-friendly rentals Monroe County
- Farm stay rentals Monroe County
- Rentals with a cinema Monroe County
- Resort rentals Monroe County
- Ski-in/ski-out rentals Monroe County
- Houseboat rentals Monroe County
- Rentals with a patio Monroe County
- Rentals with a hot tub Monroe County
- Pet-friendly rentals Monroe County
- Private suite rentals Monroe County
- Loft rentals Monroe County
- Bungalow rentals Monroe County
- Beachfront rentals Monroe County
- Fitness-friendly rentals Monroe County
- Rentals with a washing machine and dryer Monroe County
- Family-friendly rentals Monroe County
- Villa rentals Monroe County
- Bed and breakfasts Monroe County
- Rentals with breakfast Monroe County
- Boat rentals Monroe County
- Guest house rentals Monroe County
- Rentals with beach access Monroe County
- Rentals with a kayak Monroe County
- Boutique hotels Monroe County
- Campsite rentals Monroe County
- Motorhome rentals Monroe County
- Holiday home rentals Monroe County
- Serviced apartment rentals Monroe County
- Tiny house rentals Monroe County
- Rentals with lake access Monroe County
- Rentals with an accessible-height bed Monroe County
- Waterfront rentals Monroe County
- Rentals with outdoor seating Monroe County
- Aparthotel rentals Monroe County
- Townhouse rentals Monroe County
- Rentals with a firepit Monroe County
- Rentals with a fireplace Monroe County
- Rentals with an accessible-height toilet Monroe County
- Cottage rentals Monroe County
- Rentals with an EV charger Monroe County
- Luxury rentals Monroe County
- Flat rentals Monroe County
- Rentals with pools Florida
- Rentals with pools United States
- Things to do Monroe County
- Sports activities Monroe County
- Art and culture Monroe County
- Tours Monroe County
- Sightseeing Monroe County
- Nature and outdoors Monroe County
- Entertainment Monroe County
- Food and drink Monroe County
- Things to do Florida
- Food and drink Florida
- Sports activities Florida
- Tours Florida
- Art and culture Florida
- Sightseeing Florida
- Entertainment Florida
- Nature and outdoors Florida
- Wellness Florida
- Things to do United States
- Tours United States
- Sightseeing United States
- Entertainment United States
- Art and culture United States
- Food and drink United States
- Wellness United States
- Sports activities United States
- Nature and outdoors United States




