Vacation rentals with a pool in Southfield

Beautiful Oasis w/Heated Private Pool & Sunroom!

*HEATED POOL IS OPEN APRIL 1 - OCT 31* Welcome to Windsor’s largest and coziest stay! This gorgeous home blends modern design with comfort, featuring an inviting sunroom with soaring ceilings and natural light, perfect for morning coffee or quiet evenings. The chic decor creates a stylish, yet homey feel :) Unwind in a private backyard oasis with a 15x30, 8’ deep, in-ground oval pool with a brand NEW heater and BBQ lounge! Our backyard designed for a unique and relaxing family experience!

Timberline / Indoor Pool / Arcade

Escape to our Shelby Township retreat, where luxury meets comfort in a 4-bedroom ranch-style home. Dive into the private indoor pool or challenge friends in the game room. The space boasts a gourmet kitchen for culinary exploits, an outdoor lounge for serene evenings, and plush bedrooms for tranquil rest. Ideal for families or groups seeking leisure and entertainment, this home is nestled in a quiet neighborhood, minutes from golf and shopping, ensuring a stay filled with cherished memories.

Stunning spacious home! POOL Open Thru SEPT.

Have fun with the whole family at this stylish, open layout ranch house with a private heated pool and fire pit. The master bedroom and bathroom suite have his and her sinks, jacuzzi bathtub and a gorgeous two person walk in shower. The open floor plan of the living room, kitchen, dining and family room with fireplace have touches of art, nature and wood. My hope is that you will feel peaceful and elevated in your new light-filled home away from home. Pool closes mid-September through May.

Chic Retreat - Pool, Hot Tub, and Large Patio

A resort-style home with stylish vibes awaits you. A large rear patio is the perfect spot for a dip in the pool, a hot tub session, or a backyard BBQ. If you choose to stay indoors, you'll find luxury hotel vibes in every room: A fully stocked kitchen, a cozy study, and a theatre worthy basement to fulfill your binge-watching needs. When you're ready to call it a night, you'll be welcomed by high-end mattresses outfitted with linens that will whisk you into dreamland. Treat yourself today!

The Ambassador Estate Inn

A warm “welcome back” to all our previous guests and “greetings” to our new friends! A luxurious executive 7 bedroom estate property located on Windsor’s finest golf course and minutes from the Ambassador Bridge to Detroit Michigan. A beautifully appointed home nestled among rare Carolinian Forest. All the amenities of a 5 star resort with the privacy and serenity of a country estate. If you are looking for quality and relaxing luxury, then look no further than the Ambassador Estate.

Home in Royal Oak w/ pool & sauna & dream garage

Welcome home to your oasis in the middle of Royal Oak MI! You truly feel you are in the Blue Lagoon with the heated salt water pool. Dry yourself off in a spacious sauna right in the garage. The garage has been fully remodeled and offers the most relaxing environment to be in. Enjoy this home with an outdoor heated salt water pool and plenty of space to enjoy. Directly across the street, you can enjoy tennis courts, basketball hoop, baseball fields, soccer nets and much more.

The House of Pair-adise

Catch your wind in this contemporary peaceful, private unit/apartment, stylish space, recently upgraded bathroom and with a very clean beautiful hot tub, an indoor and outdoor fireplace, an in ground swimming pool(May-Sept). It consists of a spacious living area, full kitchen, contemporary bedroom, and a full restroom. It is 4 miles from Downtown Farmington, 7 miles from Birmingham, and 20 miles from Downtown Detroit, easy access to all freeways, secluded neighborhood.

Lakeshore Hidden Oasis (heated pool / jacuzzi)

Located in Lakeshore, minutes from Windsor / Detroit, a perfect oasis for the couple looking for a quiet escape. The suite's private jacuzzi tub makes it the ideal place in any season! The suite is fully equipped, including a complete kitchenette, Smart TV, etc. A private BBQ is at your door. During your stay you will have access, day and night, to our heated salt water pool. It is open from mid March to early November at 32°C (90°F). The hot tub is open year round.

Architectural Gem | Direct-Entry Pool

Welcome to Windsor’s hidden gem. This modern 2-bedroom retreat stuns with a unique sunken living room, soaring patio doors, and a heated pool just steps away. The main floor features an open-concept layout with a sleek kitchen and access to a tree-top terrace lounge. Upstairs, unwind in a spa-like bedroom with a soaker tub, rainfall shower, and rooftop retreat. With two private terraces and unforgettable design, this is more than a stay—it’s an experience.