Holiday rentals in Bear Point

Bluewater 306 Direct Gulf Front, HUGE Wrap Balcony

Bring the whole family together in this beautifully designed & thoughfull laid out beachfront condo. Offering spectacular views, multiple generous living areas & comfort for every generation. With room to gather & space to unwind, this home is perfect for grandparents, parents & kids or friend groups to share unforgettable beach days to enjoy together without feeling crowded. With panoramic views from floor-to-ceiling windows, this spacious condo offers breathtaking scenery sunrise to sunset.

Bear Point 3BR House Orange Beach Bring Your Boat!

Dream Fisher house - Orange Beach Escape to your perfect getaway in this professionally decorated 3-bedroom, 2-bathroom home located in the sought-after Bear Point area of Orange Beach, AL. Designed for relaxation and convenience, this property features a chef's kitchen adorned with stunning granite countertops and stainless steel appliances, making meal prep a delight. After a long day in the sun, retreat to the beautifully appointed bedrooms, each outfitted with comfortable Queen beds.

Spanish Moss House on Wolf Bay w/Pier + Boat Slip

This historic, century-old cottage sits directly on the sandy southern shores of Wolf Bay, beneath live oaks festooned with Spanish moss. Private pier and boat slip, just minutes from the Gulf beaches and nature trails, and next door to the community park, playground, cultural arts center, library, and popular dining spots. Enjoy relaxing on the back deck or down at the water. Delight in daily dolphin sightings, fishing off the pier, and taking in the gorgeous spring and summer sunsets.

Cozy Bayfront Apartment

Take it easy at this unique and tranquil getaway on Arnica Bay just a walk down the road to Pirates Cove. 20-30 minutes from Foley, OWA, Tanger Outlet, Foley Sports Complex, Orange Beach, and Gulf Shores. This apartment is stand-alone. It has a living room with a queen pull-out sofa bed, a full kitchen, one bedroom with a queen bed and full-size bunk beds, and one bathroom. The side door leads out to a shared breezeway with a hot tub. The pier leads out to the boathouse for fishing.

Hammock Hideaway - waterfront cabin

Backyard oasis on a deep water creek. If you are coming for travel ball, love kayaking and/or just hanging out right on the water, you will appreciate this special hideaway. A fisherman’s/nature lovers dream and truly unique rental experience at this creekside cottage with water frontage on deepwater Hammock Creek. Close to the beach but out of the congestion. We have a multi level backyard with gazebo with swing, fire pit and huge deck. Fully enjoy the wildlife and outdoor activities.

Lost Key Paradise - Luxe Cottage with Gulf View

Stunning spacious townhome, just a short walk to the soft and white sandy beach and emerald green waters of the Perdido Key barrier island. It's located in the Lost Key Golf and Beach Resort. This is a hidden gem of the Florida panhandle for a serene beach getaway with best amenities, a Championship 18-hole Arnold Palmer golf course, lighted tennis courts, two resort style pools, hot spa, fitness center, and a Beach Club with a restaurant and pool and private beachfront access!

Phoenix on the Bay, Condo on Orange Beach 1416

Escape to paradise in this stunning two-bedroom, two-bathroom condo in Orange Beach! With two king-size beds, a jetted bathtub, WiFi, and air conditioning, comfort is guaranteed. Enjoy resort-style amenities, including an indoor pool, hot tub, water slide, and lazy river. Explore nearby beaches, dining, and attractions, or simply relax in this cozy retreat. Whether seeking adventure or tranquility, this condo offers the perfect getaway. Book now for a memorable stay!

Sunny Side: Awesome Waterfront Unit with 4 Kayaks

Welcome to Sunny Side! Come enjoy fun and relaxation right outside your back door! Sitting on a calm, shallow cove of Perdido Bay, Sunny Side provides the perfect place for families to swim and play safely. This 2 bed/2.5 bath sleeps 7 people across 4 different beds and includes a full kitchen, laundry, 4 Kayaks, and more! Spend all day here, tucked away from the hustle and bustle, or take a short 5 minute drive to Perdido Key Beach, restaurants, parks, and more!

Bear Point Bayview Cottage | Bay Views & Music

Welcome to Bear Point Bayview Cottage! Enjoy stunning bay views, unforgettable sunsets, and a gentle breeze from this charming 2-bedroom, 2.5-bath retreat. With two outdoor showers and a short walk to Oso Tiki Bar and Bear Point Harbor Marina, convenience meets relaxation. Nearby attractions include The Wharf, OWA Park, and top restaurants like The Gulf and Florabama. Essentials are close by at Walmart, Rouses, and Publix. Your perfect getaway awaits—book now!

Beach Bummin’ - Gulf front 5 min walk to Florabama

This gulf side Needlerush Point condo has an awesome beach view and many shared amenities. You can walk to Florabama bar on the beach or on the sidewalk! This condo has 700 feet of beach so there is never overcrowding..You also have access to the bay side with boat slips and trailer storage during your stay. When you're not enjoying the beautiful beach or Old River views you can play pickle ball or tennis on our shared courts.

Casa Verde: Heated Pool +JET SKI & Pontoon rental

Across the street is the ocean & behind the house is the lagoon; it's the best of both worlds. Swim, fish, crab & paddle board in the lagoon, then swim in the ocean & chill on the beach. Rinse off in the outdoor shower & enjoy the heated pool. FYI: pool heating costs extra: $50 per day (for 8 hours of heating - you pick the hours). You're welcome to use the Green Egg grill. We rent kayaks, a paddle board & a jet ski too.

Baydreamer- Beach House: Perdido Bay/Orange Beach

Bay Front Home With Private Beach on Perdido Bay! AMAZING VIEWS!!! Nestled on a quiet peninsula overlooking beautiful Perdido Bay and the Intracoastal Waterway in the Josephine community. This 3 bed, 2.5 bath offers the perfect place for any vacation getaway! The best of both worlds is at your pleasure of a tranquil waterfront setting as well as the convenience of walking out to the beach from your back yard.