Vacation rentals with outdoor seating in Holmes Beach

Carissa A | Beachside Duplex | Golf Cart | Pool

Welcome to Carissa Loft A, your completely private half of a beachside duplex on AMI! The duplex is designed back-to-back, meaning you have your own private indoor and outdoor spaces, entrance & pool-No shared amenities! Loft A includes: 3 beds, 2 baths, full kitchen, 2 separate living areas, balcony, heated/cooled cocktail pool, & garage w/golf cart! Ideal for up to 6 guests. Need more space? You can book both sides of the duplex for larger groups while still enjoying separate living areas.

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Crows Nest at Spinnakers Vacation Cottages

Close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love the location, the ambiance, and the high ceilings. Located in the lush tropical paradise of Spinnakers Vacation Cottages. Offers a spacious living area, with the bedroom and bathroom on the living floor with a spiral staircase leading to a loft with two twin beds. Great for couples, families and dogs (with small pet fee) Great private deck for star gazing! Spa maintains same temperature as pool

Walk to beach! Private pool! Sea Star Cottage

Private HEATED POOL-two minute walk to the BEACH. 2 bed/2bath home with private backyard and covered lanai. Beautifully decorated and centrally located near shops and restaurants.Enjoy a quiet setting off the main road. Modern amenities and plenty of seating options. Gas grill. Please be a good neighbor by keeping noise levels to a respectable level during the day and night. Excessive noise can deprive neighbors of the peaceful enjoyment of their private property. VRC 19-000082 license #

Island Time: Open Sunday Nite, 10% Off!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Heated Pool, Hot Tub, Game Room, Steps to Beach!

Welcome to Island Dreams, the ultimate peaceful escape just 4 min walk from Anna Maria Island's stunning beaches. This fully renovated three-bedroom, three-bath beach house features a Zen-inspired backyard oasis, a private cocktail pool, and a game room! Walk to shops, restaurants, and the trolley stop! Island Dreams offers the perfect blend of relaxation, location, and indoor and outdoor fun! NOTE: Holmes Beach has a 7-day rental minimum. Check in / Check out days are on Saturdays.

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Retreat at Solace West-Hot Tub/Fire Pit/Sunsets

Welcome spring with sunshine, sea breezes, and island charm at Solace West. Just a short walk to the beach, spend your days soaking up the sun, biking along the coast, or hopping on the FREE trolley to explore AMI’s local favorites. It’s the perfect place to relax, recharge, and enjoy the laid-back coastal lifestyle. After a day in the sun, unwind in the hot tub or gather by the fire for a peaceful evening. Fresh air, warm days, and easy island living—your spring escape starts here.

Anna Maria retreat house

Elevated home with all the amenities. Walking distance to the beach, chairs and towels provided. Relax in the backyard patio, including pool with waterfall . The shaded balcony overlooks the pool if you need to escape the sunshine. There’s a free trolley that runs all day in AMI if you don’t want to take the car out. The house is located across the street from Bimini Bay, enjoy a jog through these side streets in the morning. Local shops and restaurants that will not disappoint .

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated PRIVATE pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

Luxury 2BR Oceanfront Condo + Rooftop Patio

Modern Condo with Stunning Ocean Views: - Cozy turf patio - Smart TVs and high-speed WiFi - Fully equipped kitchen - Two private parking spots for hassle-free stays - Just a 2-minute walk to the beach Unique Features: - Social Media worthy grass wall - Two comfortable beds: one king & one queen, ensuring a restful sleep - Queen-sized inflatable extra bed Prime Location: - Conveniently located next to the AMI trolley stop - Within walking distance to dining, a gym, and more!

Pergola Oasis | Walk to Beach + Outdoor Living

Welcome to Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to the white sandy beaches of Anna Maria Island, this home features a private covered pergola with outdoor lounge seating and dining, creating the perfect space to relax day or night. Steps from shops and eateries, with nearby bike and golf cart rentals, plus access to community amenities including a boat ramp, kayak launch, fishing dock, and tennis & pickleball courts.