
Holiday rentals with a pool in Cutler Bay
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Top-rated rentals with a pool in Cutler Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

King Bed Home by the Bay FAST WI-FI & Coffee
Whether you are visiting the Florida Keys, the beaches of Miami, or looking for a comfortable staycation, discover what South Florida has to offer while feeling at home. You'll be located near Southland Mall, The Falls Shopping Center, Black Point Marina, Miami Metro Zoo, Deering Estates, the Dennis C. Moss Arts Center and more! ❧ 48 minutes from the Florida Keys. ❧ 37 minutes from Miami Beach. ❧ 33 minutes from the Everglades. Message us about long stay, military, & first responder discounts.

Cozy private guest studio
Welcome! This is a private guesthouse located in a quiet neighborhood. Accommodations are with a private entrance and parking space to make you feel at home. We are located near a major expressway. We have a pool; The POOL is a SWIM AT YOUR OWN RISK. It is shared with Owner. Enjoy a smoke free cottage. Ashtrays are provided outside for those guest that do smoke. We provide a queen size bed and a couch/bed. This space is perfect and comfortable for two guest.Please NO children and NO animals.

Stunning Studio w/Bay & City View Free Park/Pool
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 deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

Very Private 1/1 Apt w/Oasis Pool Patio Setting
Private apartment-1 bedroom w/king size bed, 1 full size bathroom, separate living and dining area. Fully equipped kitchen. Free parking, beautiful oasis setting with salt water pool, hot tub & patio. Gazebo w/fire pit, Bar-be-cue, 2 TV’s, free WiFi. This is NOT a party spot but a place to relax in the pool, hot tub or relaxing dinners at home after visiting Miami venues. Set in a quiet neighborhood, 2 miles from shopping & restaurants. This is your home away from home vacation spot!

Cozy house
Welcome to Your Tranquil Getaway! Discover a serene escape at our unique and tranquil retreat, perfect for families and friends seeking relaxation and adventure. This beautifully designed property features a sparkling private pool, ideal for enjoying sunny days and creating lasting memories. Nestled in a prime location, you’re just minutes away from top attractions such as Monkey Jungle, the Miami Metro Zoo, Black Point Marina, and the Florida Keys. Explore nearby gems like Gilbert’s Resort.

Artistic Design District Stay, Parking, Pool, Gym
Modern, boutique condo with outstanding amenities located steps from the famous Miami Design District. Your unit includes: a washer/dryer, full kitchen (with stove, oven, microwave, fridge, dishwasher, Keurig coffee maker, toaster, blender, tupperware, utensils, plates and cookware). Building amenities feature a beautiful gym with virtual spin studio, common work space, pool and parking garage. Your unit has a relaxing private balcony. Safe, secure building with 24/7 security and front desk.

Family retreat oasis, heated pool, jacuzzi & grill
Welcome to Forget-me-not Villa, a sanctuary for your family and friends to let loose barefoot and unwind in the private backyard fully fenced, feel the breeze, stargaze at night, and savor the comfort of our exquisite vacation home. The villa features a heated pool and jacuzzi, a grill station, a love seat for romantic moments, a playground for children, an Xbox S for gamers, board games, mini golf, pool volleyball and basketball hoop, Smart TVs& high-speed Wi-Fi & electric car connection.

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

1205 Ocean View 1BD Free park Monte Carlo Collins
APART HOTEL. 24/7 FRONT DESK. FREE VALET PARKING. BEAUTIFUL OCEAN VIEW WITH BALCONY, 1 BEDROOM, 1 BATH LOCATED AT A LUXURY OCEAN-FRONT CONDO "MONTE CARLO" ON COLLINS AVE, MIAMI BEACH. UNIT HAS: WI-FI, KING SIZE BED, SLEEPER SOFA, ROLL-AWAY BED, CRIB, 2 TV'S, LAUNDRY, DISHWASHER, FULL KITCHEN AND FREE PARKING 2 SWIMMING POOLS, JACUZZI, GYM, STEAM ROOM, LOUNGE ROOM DIRECT BEACH ACCESS, LOUNGE CHAIRS AND UMBRELLAS AVAILABLE AT THE BEACH. WI-FI THROUGHOUT THE BUILDING. NETFLIX, HULU.

Cozy Suite -Exterior Entrance, SelfCheckin
If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Room 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 -Bathroom with 2 sinks -SWIMMING POOL -Central A/C -HBO TV -Refrigerator -Ceiling Fan -Closet Space -Ceramic Tile Floors -Iron & Board -Towels & Bath essentials -Hair dryer

Private Waterfront Studio Paradise
Casa Cocos is a private studio, with a private entrance, bathroom and kitchenette, and free and secure parking. It is nestled in Florida's tropical waterfront paradise. Come enjoy the views of the garden, go for a swim, paddle board, canoe, kayak, grill, take a nap in a hammock, and just relax. Casa Cocos is surrounded by nearby restaurants, bars, retail stores, malls all within walking distance or a short drive. 30 minutes to airport, downtown, South Beach, Keys, and Everglades.

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.
Popular amenities for Cutler Bay rentals with a pool
House rentals with a pool

4BR Miami Villa | Heated Pool | BBQ | Near Beach

Spanish House 3 Bedroom Pool House

Hollywood Sunshine Resort Pool House w/ Hot tub

Poolside Haven 4/2, Htd pool, oudr ktch by freeway

Miami Getaway - Heated Pool, Hot tub, BBQ

Spectacular Villa in Miami w/Pool/Games/BBQ/Gazebo

Centrally Located Resort Style Miami home

Heated Pool/Basketball Court/Ping Pong Table/Golf
Apartment rentals with a pool

Awesome 1b on the Beach in South Beach with Pool!

Feels Like Summer ~ Panoramic Water Views! 2BR

Breathtaking OceanFront - 15th Floor (+Resort Fee)

Gorgeous Beachy Chic Condo in Key Biscayne

Beautiful apt. 1st floor 2/2. wifi and parking

Front Facing Top Floor Penthouse with Ocean Views

Key Biscayne little beach place

Stunning 2 bedroom+17 foot ceilings & heated pool
Other holiday rentals with a pool

Hidden Gem. Luxe 1BR w/Patio

Miami Oasis with Luxury Spa & Your Own Helicopter

South Miami Gem!

Cozy and charming cottage

Paradise in Palmetto Bay, with Pool-BBQ-Gazebo.

Ultimate Heated Pool Escape:Midway to Keys & Miami

Escape to Miami/Heather+Pool/9pl/BBQ/pool table.

Waterfront Miami Villa | Pool, Kayaks, Mini Golf
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $290 SGD | $284 SGD | $337 SGD | $299 SGD | $304 SGD | $326 SGD | $339 SGD | $329 SGD | $302 SGD | $308 SGD | $337 SGD | $397 SGD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about holiday rentals with a pool in Cutler Bay

Total holiday rentals
Explore 60 holiday rentals in Cutler Bay

Nightly prices starting at
Cutler Bay holiday rentals start at $63 SGD per night before taxes and fees

Verified guest reviews
Over 3,120 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Cutler Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Cutler Bay rentals

4.7 Average rating
Cutler Bay stays receive an average rating of 4.7 out of 5 from guests
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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- The Tides on Hollywood Beach
- Miami Design District
- Bayside Marketplace
- Brickell City Centre
- Miami Beach
- Miami Beach Convention Center
- Kaseya Center
- Hard Rock Stadium
- Midtown
- Everglades National Park
- Port Everglades
- Haulover Beach
- University of Miami
- Ocean Reserve Condominium
- Sawgrass Mills
- Calle Ocho Plaza
- Las Olas Beach
- Lauderdale-By-The-Sea Beach
- LoanDepot Park
- Bal Harbour Beach
- Aventura Mall




