ProActive Properties - Maine & Florida Vacation Rentals

Waterfront homes, Ski Retreats, & Sunny Escapes - Be ProActive, Book Direct & Save on Your Next Vacation

Our Properties

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Maine, The Way Life Should Be…

Discover Maine “The Way Life Should Be.” From mountain adventures and peaceful lakeside escapes to charming coastal villages and breathtaking lighthouses, our homes put you at the heart of it all.

Stay with us and experience the beauty, comfort, and unforgettable moments that make Maine the perfect destination for family and friends.

Your adventure starts here. ✨

 

Beaches, Golf & Sunshine Your Naples Escape

Stay 30+ days and enjoy full membership perks at Cypress Woods Golf & Country Club:

  • Unlimited golf, pickleball & tennis – right outside your door

  • Multiple pools & a vibrant social calendar

  • Join leagues, events & activities with a welcoming community

  • All just 15 minutes from the white-sand beaches of the Gulf

Sun, sport & friendships await – every day feels like a holiday!

Naples Condos Pool and Pickleball
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White Sand Beaches, Private Pool in Bonita Springs, Florida

A peaceful 2 bed/2 bath retreat with a private heated pool and Spanish-inspired lanai. Just 3 miles from Bonita & Barefoot Beach and 1 mile to Downtown Bonita Springs.

Thoughtfully furnished for comfort and style, the perfect spot to relax, recharge, and enjoy Gulf Coast sunsets.

What We Offer

Luxury Vacation Rentals

Stay in beautifully maintained homes with modern amenities that blend comfort and style for every guest.

Pet-Friendly Stays

Bring your furry friends along—many of our Maine and Florida vacation rentals are fully pet-friendly.

Family-Focused Comfort

Enjoy spacious layouts, child-friendly features, and multiple bedrooms, perfect for families and groups.

Adventure-Ready Locations

Our properties put you close to skiing, hiking, mountain biking, boating, and world-class golf.

Year-Round Escapes

From cozy winter ski cabins to summer waterfront retreats, we offer destinations for every season.

Personalized Guest Experience

As a Superhost, Jeff ensures every stay includes thoughtful touches, responsive communication, and seamless booking.

MEET the Hosts

ABOUT US

We’re Jess and Jeff Davis, co-founders of ProActive Properties. We have been hosting together for over a decade. As superhosts with hundreds of 5-star reviews, you can see for yourselves that we go above and beyond to make every stay a special one. We are the top hosts in every market that we service – reach out and ask us how we can help you get the most out of your property.

Jeff Davis family photo cropped
MEET the Hosts

ABOUT US

We’re Jess and Jeff Davis, co-founders of ProActive Properties. We have been hosting together for over a decade. As superhosts with hundreds of 5-star reviews, you can see for yourselves that we go above and beyond to make every stay a special one. We are the top hosts in every market that we service – reach out and ask us how we can help you get the most out of your property.

Explore Our Vacation Rentals

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Frequently Asked Questions

Please check listing for full details on arrival and departure times. 

Yes, most of our properties are pet friendly. Please verify that the property you are booking is pet friendly prior to completing your reservation, and indicate that you are brining a pet on the booking form.

Yes! All of our properties allow children of all ages and are family friendly.

While we encourage all guests to have a wonderful time and enjoy their stay with us, we do not allow any events or parties that exceed the occupancy limits set forth in each listing.

We provide all bath towels and linens at each of our homes. We have towels for the lake, beach, hot tub and pools at specific homes. If you prefer the use of washcloths, we ask that you please pack one of your own.

Each home/rental has specific details and amenities that are up to date on their specific pages. We find it a hassle to have to get simple things like toilet paper or laundry detergent when we travel, so we make sure to have our rentals fully stocked and ready for you!

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