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Holmes Beach Vacation Rentals on Anna Maria Island

Book Your Holmes Beach on Anna Maria Island Vacation Rental Directly Online Here and Save!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Holmes Beach on Anna Maria Island, Florida.

Oleander Villa 105 - Holmes Beach Cottage

1 Bedroom Tropical Romantic Getaway Close to Beach/Pets ok

Island Garden Villas will amaze you with it's old Florida charm and lush tropical surroundings. Oleander Villa is a true island oasis! *Features include* * 1 Bedrooms and 1 full bath * King bed and Queen sleeper sofa * Botanical courtyard with beautiful fountain * Stunning tropical landscape * Designated patio off the courtyard * Only steps away from the beach path * Beach supplies provided * Ground level * Dog and small pet friendly.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 3 Cottage Rentals

Vacation Home

Bay Breezes at Bayside Bungalow - Holmes Beach Apartment

Adorable 2 bedroom luxury Resort Unit in a perfect location! Great Pool area!

*The City of Anna Maria, Holmes Beach, and Bradenton Beach all have noise ordinance policies in place, and they are enforced by local law enforcement and code enforcement officers. The goal of this program is not to limit your fun or vacationing experience, instead it is designed to ensure a quality stay for every guest and resident on our island. Please be mindful of our neighbors during your stay. Exceeding the noise ordinance could result in d.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 6 Apartment Rentals

Vacation Home

Fairwinds - Holmes Beach House

FAIRWINDS: Amazingly Perfect Island Home with Everything, Heated Pool, Hot Tub

******Please Read our Property Manager Notes Below ****** BEFORE YOU BOOK: We rent Saturday to Saturday…Usually. If you are interested in starting or ending on a different day other than Saturday, then Please contact us before you book by clicking the “Ask Manager a Question” button to send us a message with your desired dates. We’ll let you know if we can accommodate within 24 hours Monday through Saturday. Messages received Saturday eve.......read more

5 Bedroom(s)
5 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Casa Azul - Holmes Beach House

Casa Azul - Close to beach, 3 bd plus private pool! Awesome location

Casa Azul is a 3 bedroom, 3 bath, luxury beach house just 600 steps from the sparkling waters of the Gulf of Mexico and white sandy beaches of Anna Maria Island. Completely updated with designer furnishings and luxury amenities abound, including: a free form heated pool with tiki bar, outdoor shower, grill and al fresco dining, fabulous chef's kitchen with granite counters and bar seating, high ceilings, recessed lighting, and a beautiful collec.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Almost Heaven AMI - Holmes Beach Condo

Spacious Condo on the Beach

Newly remodeled condo with a view of the gulf from your relaxing balcony. Large heated pool and hot tub amid lush landscaping, then walk through the gate straight out to the beach. Stylish, clean, and comfortable interior awaits you. New flooring, countertops, appliances, paint, decor, tvs, linens & dishes. Beach accessories are available; including chairs, umbrella, and beach towels. The perfect location on the island. Tennis courts and shuffle .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Sandy Point Cove 114 - Holmes Beach Condo

Sandy Point Cove 114

Sandy Point 114 - Townhouse 3 Bedroom/ 3 Bath, maximum occupancy of 6 people. Distance to the Beach: 4 blocks. Community pool. VRC16-000070 This 3 bedroom , 3 bath townhouse condo features 2 living floors and 3 verandas above an enclosed over-sized garage and located in the Cove at Sandy Pointe on beautiful Anna Maria Island! On the first floor there is a large living/dining area with outdoor veranda for wining and d.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Island Retreat - Holmes Beach Townhome

Island Retreat is less than a 3 min walk to the white sandy beaches

Welcome to Island Retreat where you can enjoy the tranquility of listening to waves, watching dolphins, coastal birds and sunsets you'll remember for the rest of your life. This beautifully remodeled 1 bedroom 1 bathroom condo has everything you will need to make everlasting memories of adventure and fun. Not to mention it is within walking distance of everything you would need during your island stay, Less than a 5 min walk to the beach, Publix .......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Townhome Rentals

Vacation Home

Vacation Rentals - Holmes Beach Villa

Just a Stones Throw from the beach

This pet friendly (under 40 lbs) 2BR/1BA owner’s side of a duplex is less than 150 steps to the beach! The unit includes a king size bed in the master, queen size futon and full size bed in the second bedroom and screened-in porch. Plenty of space for a backyard BBQ and attached laundry room. Everything you need to stay for a few weeks or all season! Get this prime location that is just a stones throw away from the best stretch of beach on Anna.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 3 Villa Rentals

Vacation Home

Blissful Beach Retreat - Holmes Beach House

Wonderfully Updated Beach Escape W/ Fast WiFi & Short Walk to Sugar-White Sand!

Blissful Beach Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Welcome to paradise by the beach! An opportunity like this doesn't come around often, as this home is located west of Gulf Drive and steps away from the Gulf of Mexico! The secluded location is away from the traffic noise and just steps to a private beach, so you will have your own sense.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Casa Riva - Holmes Beach House

Casa Riva - Beach House Real Estate

Casa Riva is centrally located in Holmes Beach near the beautiful beaches of Anna Maria Island. The sand will brush away, but the memories you make here will last a lifetime! This light-filled condo is situated in the quiet North Beach Village community just over 2 blocks to the sugary sand and turquoise water of the Gulf of Mexico, and an easy walk to the shared heated pool. Open the sliding doors to let breezes in from the screened lanai, whil.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 4 House Rentals

Vacation Home

Gone Coastal - Holmes Beach House

Gone Coastal - Block to Beach - Brand New Heated Pool and Spa!

Come check out Gone Coastal on Anna Maria Island! This gorgeous duplex that was just completely renovated! Enjoy both sides of this adorable beach cottage. Perfect for two families vacationing together! Enjoy hanging out together at the pool and have you own space later when it is time to wind down after a long, fun day. Each side features 2 bedrooms and 2 baths, a fully stocked kitchen, and a super comfortable and chic living room. There is a.......read more

4 Bedroom(s)
4 Bath(s) - Sleeps 8 House Rentals

Vacation Home

01 Studio King - Holmes Beach Hotel

Beach-pool- 2 Room Studio With Kitchen #1

You're steps from the beach in this two room studio! This charming studio has a full separate kitchen with a dishwasher, a comfy king-sized bed, tv and a table for two. The bathroom has a walk in shower. Haleys Couples Retreat is the perfect blend of old-Florida romantic charm and modern comforts. Proudly holding TripAdvisor ;Certificate of Excellence for15 years. You're welcome to enjoy the entire grounds of our tropical retreat, includes: .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Hotel Rentals

Vacation Home

Gulf Sound - A - Holmes Beach Cottage

Ground Floor Condo, Three Houses from the Beach with Large Heated Pool

Overview Gulf Sound is a gulf side, ground level tri-plex located on Gulf Drive in the southern end of Holmes Beach. Unit A at Gulf Sound is the southern unit. It is a two bedroom, one bath that will sleep six people. The unit has been updated and is comfortably furnished. It's quiet, yet close to shopping, restaurants and trolley stops. Best of all, this unit is west of Gulf Drive for easy beach access. There are no busy streets to cross and ev.......read more

3 Bedroom(s)
1 Bath(s) - Sleeps 6 Cottage Rentals

Vacation Home

Rays N Waves - Holmes Beach House

Rays N Waves in Holmes Beach

Rays N Waves is a three bedroom, two bathroom beach cottage with a pool and spa. This fabulous house is only a short walk to the white sand beaches of Holmes Beach. Dine out at one of the many fine restaurants on the Island. Don't forget to explore on the free Island trolley that runs all day, every day from the end of Pine Avenue to Coquina Beach. Rays and Waves has all the charm of Old Florida ground level living with modern updates.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

The Gables - Holmes Beach House

The Gables offers southern charm and short walk to the beach

The Gables is a charming 4 bedroom / 2.5 bathroom southern style home that features a private pool and is centrally located in the heart of Holmes Beach and within walking distance to the white sandy beaches. The furnishings and facilities are of the highest quality to make your vacation one to remember. We know once you spend time here you will not want to leave or you will want to return time and time again. This tropical retreat and luxurious .......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home

AMI Villa - Holmes Beach House

Gorgeous Tuscan Villa w/Private Pool~Walk 2 Beach!

Welcome to Paradise - AMI Villa! Make this charming 3 bedroom, 3 bath Mediterranean beach villa your home away from home! With much to offer, this home will have your family wanting to return to Anna Maria Island year after year. *Features include* * 3 bedrooms, 3 full bathrooms * 2 King master bedrooms * 2 Queen beds in 3rd bedroom * Private, heated tropical pool * 3 covered patios on different levels including a rooftop patio with a swi.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

510 Bayview - Holmes Beach House

510 Bayview in Holmes Beach

510 Bayview - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. VRC#20-000114 Island Elegance for the whole family!~ Distance to the Beach: 2 blocks Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and surf. Relax in well-appointed rooms, dine alfresco, cruise from your private dock to the bay and private pool, or you simpl.......read more

5 Bedroom(s)
5 Bath(s) - Sleeps 10 House Rentals

Vacation Home

Castnetter Beach Resort 5 - Holmes Beach Building

Castnetter Beach Resort 5

Our Holmes Beach property is located at Gulf Drive & 41st Street. Conveniently located at the (7) Acre Lifeguard protected Manatee Public Beach. Enjoy the views of the Gulf at the Beach Cafe, a great spot for pancake breakfast, lunch and live entertainment as well as a playground for the kids. Steps away you'll find the West Coast Surf Shop stocked with beach apparel and supplies. The legendary "Skinny's Place" is right across the street, se.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Building Rentals

Vacation Home

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