Vacation rentals with a pool in Holmes Beach

Green Jacaranda AMI Duplex B, 5 min walk to beach

Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

Gulf Water Views - 3 Bed 2.5 Bath - Pool & Hot Tub

Step into Sunset Shores, a sun-kissed three-bedroom, two-and-a-half-bath condo. Nestled on pristine Gulf sands, the condo is located in the Gulf front complex of La Casa Costiera where beach days meet upscale comfort. Why This Place is Special Water views from living room window and private balcony! Easy beach access, no streets to cross Shared pool and an in-ground spa Picnic area with a gas grill, charcoal grill, and an outdoor fireplace Beach gear provided 3 King beds 2 dedicated parking

Sea 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.

250 steps from Beach Access! Heated pool and spa

Steps from beach access! Welcome to "Pirates Den" at the Gulf Drive Inn - a spacious 1 bedroom/1 bathroom suite with a sleeper sofa, full kitchen and living area. This duplex style bungalow has resort-like amenities with a shared backyard space including a heated saltwater pool, spa and gas grill. Whether you're celebrating a birthday, anniversary, or simply in need of an extended beachside stay, The Gulf Drive Inn has it all!.Please inquire to reserve more than one suite for larger parties!

Short Stroll to the Surf! ~ Make Memories on AMI

Nestled in a charming, quiet community of just 8 units, this beautifully updated beach condo offers the perfect blend of relaxation and convenience. The condo is just a short stroll (about 150 steps!) to the pristine white sand beach, where you can soak up the sun and enjoy the coastal views. Wonderful family getaway or couples escape. Private, covered 2 car parking. Laundry in unit. Beach wagon, chairs and gear available. A hidden gem close to everything you need for a relaxing island stay.

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean & comfortable. Sandy Pointe II is in a secluded setting, an easy walk to a less crowded, quieter section of beautiful AMI beach. VRC # 20-000-272 Minimum stay 7 nights, Adult occupancy/4 , parking 2 vehicles & Quiet hours, 10 PM untill 7 AM From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! FREE Island trolly just steps from entr

Salty Harbor AMI pool retreat near the Beach

Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

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

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly just 5 min. walk to the beach. Private lagoon-style *heated* saltwater/low chlorine pool amid lush landscaping with gorgeous rock waterfall. New appliances, HVAC, 60-inch Sony HDTV, Italian leather reclining sofas, BBQ, beach gear, three king bedrooms, all linens provided. Classic Florida one-level home - no stairs. Managed directly by owners, so no crazy fees.

Cabin 2 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.