Vacation 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.

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Guest favorite
A spacious suite featuring a king size bed with crisp white linens. Dark accent walls provide contrast against light wooden flooring. Natural light enters through large windows adorned with sheer curtains, while a small desk and tasteful decorative elements complete the stylish environment.
Apartment in Miami
4.81 out of 5 average rating, 126 reviews

Coconut Grove Stunning City View Suite Free Park

INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! In Coconut Grove, this privately owned & renovated bright suite on the 15th floor of a luxurious waterfront property offers breathtaking city views, is fully equipped for 2 w/ a king size bed & full bath. Enjoy all the luxury amenities this property has to offer, pool & hot-tub with incredible bay views, penthouse gym, sauna, business center, 24-hr security, squash

Top guest favorite
A spacious driveway curves past vibrant tropical plants and palm trees leading to a welcoming entrance of the property. The house features a warm orange exterior with decorative elements and a large garage door, complementing the lush landscaping.
Guest suite in Miami
4.9 out of 5 average rating, 389 reviews

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

Guest favorite
An open living area features a white leather sofa, a coffee table with magazines, and two ottomans in teal. A mounted TV is positioned on a white console, while a dining area is visible in the background, showcasing a modern kitchen design.
Apartment in Miami
4.95 out of 5 average rating, 242 reviews

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

Top guest favorite
A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.
Home in Key Colony Beach
4.96 out of 5 average rating, 134 reviews

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.

Guest favorite
The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.
Home in Upper Sugarloaf Key
4.94 out of 5 average rating, 109 reviews

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.

Guest favorite
Condo in Key Colony Beach
4.93 out of 5 average rating, 263 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Guest favorite
A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.
Condo in Key West
4.89 out of 5 average rating, 270 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

Top guest favorite
A serene outdoor space includes a swimming pool surrounded by terracotta tiles and lush tropical vegetation. A tiki hut is positioned in the background, with an evening sky showcasing warm tones of orange and yellow. Soft furnishings and a relaxed seating area are visible nearby.
Tiny home in Cutler Bay
4.98 out of 5 average rating, 261 reviews

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. Enjoy the miles of nearby walking paths stretching from Coconut Grove to Black Point Marina.

Top guest favorite
Condo in Miami
4.99 out of 5 average rating, 131 reviews

Your Bay View Escape in Coconut Grove, Pool & Gym

- Enjoy breathtaking bay views & sunsets in this fully remodeled Coconut Grove condo - Private balcony perfect for relaxing and taking in the scenic surroundings - Full access to building amenities, including a gym, pool, sauna/steam room and jacuzzi -Onsite restaurant, valet/parking and 24/7 security. - Located just steps from Coconut Grove’s best restaurants, shops, and marinas -Fully equipped kitchen, luxurious oversized shower and cozy bedroom with work desk.

Guest favorite
A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.
Cottage in Islamorada
4.97 out of 5 average rating, 130 reviews

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

Top guest favorite
A colorful hammock is suspended between two palm trees, inviting relaxation beside a sparkling pool. Lush tropical plants surround the outdoor area, creating a peaceful ambience. The inviting pool area is visible in the background, enhancing the serene outdoor setting.
Guest suite in Homestead
4.99 out of 5 average rating, 176 reviews

“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.

Top guest favorite
A serene canal-front dock area is shown, featuring several white, wooden lounge chairs arranged for relaxation. Kayaks in vibrant colors are secured nearby, surrounded by lush greenery and calm waters reflecting the clear blue sky.
Guest suite in Tavernier
4.98 out of 5 average rating, 329 reviews

Key Largo! Tavernier! Welcome to Paradise!

A perfect tropical getaway! Life is good today! Bright, airy, 500 plus sq ft., canal front studio, close to the bay. From the dock you can KAYAK to mangrove tunnels, fish, or just relax. Cold drink in your hand, life is good today! You are going to have an awesome vacation!! ( NOTE: THE POOL MAY BE SHARED ON OCCASION, WITH OUR FAMILY. A SIGNED LIABILITY RELEASE IS REQUIRED AT CHECK IN )

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