Holmes Beach Florida Vacation Rentals, Hotels & Places To Stay

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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Holmes Beach, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Holmes Beach townhome

BEACHY TOWNHOUSE 102

*** JUST REDUCED *** BEACH TOWNHOUSE 102 2 BEDROOM 2.5 BATH - SPLIT LEVEL "GREAT BEACH LOCATION "

BEACHY 102- Plenty of room for the whole family , a Spacious 2 bedroom 2.5 Bath Townhouse (1 queen in Master and 2 Twins in guest bedroom), full kitchen and en-suite laundry with TVs in the living and master bedroom. Great location just across from t ....

2 Bedroom(s) 3 Bath(s) Townhome
Holmes Beach, FL

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Holmes Beach house

Gulf Breeze

Gulf Breeze: Pet-Friendly Private Pool Home Just Steps from Beach!

GULF BREEZE Gorgeous sunsets are yours for the taking every evening while staying in this fabulous vacation rental in Holmes Beach on Anna Maria Island. Come enjoy this lovely three bedroom, two bath Villa with a private pool, located just steps f ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Holmes Beach, FL

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Holmes Beach apartment

Sunset Inn Holmes Beach Unit 2

Sunset Inn Holmes Beach Unit 2

The Sunset Inn is conveniently located on Gulf Drive only a block and a half from the white sands of Holmes Beach. Short walk to shopping and restaurants. Free trolley stop across the street will take you anywhere on the island. Relax by the pool ....

1 Bedroom(s) 1 Bath(s) Apartment
Holmes Beach, FL

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Holmes Beach house

Franks Beach House

Franks Beach House - Near Manatee Public Beach

Property Location When you stay at this vacation home in Holmes Beach, you'll be next to a golf course, within a 10-minute walk of Tampa Bay and Manatee Public Beach. This golf vacation home is 9.6 mi (15.4 km) from IMG Academy and 2.6 mi (4.1 km) ....

4 Bedroom(s) 0 Bath(s) Vacation Rental
Holmes Beach, FL

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Holmes Beach condo

Vacation Home

Anna Maria by the Bay

Beautifully furnished bayside condo with gorgeous relaxing view. End unit, many windows let the sights in from every angle! Sleeps six, king beds in both suites. TV’s in both bedrooms with cable and Roku. Fully equipped updated kitchen, bar and d ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 4
Holmes Beach, FL

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Holmes Beach condo

Alamanda Villas 5

Alamanda Villas 5 Beach Side Condo With Heated Pool

VRC16-000514Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beach side complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches ....

1 Bedroom(s) 1 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach condo

Vacation Home

Anna Maria Island Beachfront Condo w/ Ocean Views

Your ultimate Florida getaway starts right here at this ideally located 2-bedroom, 2-bathroom vacation rental condo situated right on the beach. Boasting 1,500 square feet and accommodations for up to 6, this open concept condo offers direct access t ....

2 Bedroom(s) 2 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach house

Bman Beach Cottage

2BR 2BA Overlooking Pool, WIFI, Close to Beaches and Trolly Pet Friendly

The Bman Beach Cottage located at 2812 Avenue B in Holmes Beach is a cute 2 bedroom 2 bath private home. This ground level home has two screened lanais one overlooking the pool and Jacuzzi. The kitchen has been newly updated as well as one of the bat ....

2 Bedroom(s) 2 Bath(s) Vacation Rental
Holmes Beach, FL

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Holmes Beach condo

3607 East Bay Dr. Unit 107 Holmes Beach

Walk to the beach, restaurants, & shopping from this recently remodeled condo, w/o the high prices!

Looking for an island getaway without all the hassle? Weâ??ve pretty much thought of everything, so you donâ??t have to. Whether youâ??re looking to relax or party it up â?? you found the right place. Located on Anna Maria island, best known for ....

2 Bedroom(s) 2 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach cottage

Songbird Cottage

Happy Days on Anna Maria Island

Staying here amplifies the feeling of Anna Maria Island with that old Florida feel. Instant relaxation in a quiet neighborhood yet near most everything. There are things in the unit that could be more high-end or updated or there are units closer t ....

2 Bedroom(s) 1 Bath(s) Cottage - Sleeps 5
Holmes Beach, FL

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Holmes Beach house

Coconut Hideaway

Stunning Luxury Beach House, less then a block from beautiful Gulf Coast beaches!

Welcome to Coconut Hideaway located just one house away from the Gulf beaches of Anna Maria Island. This beach house has a private patio surrounded by tropical landscaping where you can enjoy the pool, outdoor shower and Weber grill. In the garage, ....

4 Bedroom(s) 5 Bath(s) Vacation Rental - Sleeps 8
Holmes Beach, FL

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Holmes Beach house

Bay Palms

Bay Palms Private Home with Brand New Pool

Bay Palms is a lovely three bedroom, two bath pool home located in a quiet, residential northern Holmes Beach location at 409 Bay Palms Drive. This spacious home features a large screened in lanai, fenced yard and updated kitchen. A full size laundry ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Holmes Beach, FL

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Holmes Beach condo

Castnetter Beach Resort 5

(2) Bedroom (2) Bath with Private 10' x 30' Sun Deck

Anna Maria Island's "Castnetter 5" is a delightful Island local located directly across the street from the seven acre "Manatee Public Beach" and the Gulf of Mexico. This beautiful and totally renovated two bedroom unit with (2) Full Baths, sleeps si ....

3 Bedroom(s) 2 Bath(s) Condo - Sleeps 6
Holmes Beach, FL

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Holmes Beach condo

Ocean View

Holmes Beach on Anna Maria Island Vacation Rental Cottage Steps to the Beach

Relax to the sound of waves crashing with views of the ocean from almost every window in this cozy cottage. This second floor cottage is only steps away from Holmes Beach and overlooks the calm waters of the Gulf of Mexico. The perfect location of ....

2 Bedroom(s) 1 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach villa

Gone Coastal Too

Fall Vacation Sale!!! Prices Reduced! Gone Coastal Too: Beautiful Family & Pet-Friendly Private Home with a Heated Salt Water Pool!

GONE COASTAL TOO Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach. Insi ....

2 Bedroom(s) 2 Bath(s) Villa
Holmes Beach, FL

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Holmes Beach condo

SUMMERHOUSE A

NEW PROPERTY!! New beautiful property with heated pool, 100m to the beach!??????

This beautiful home has two separate units, A and B. The downstairs unit A has been completely remodeled and has two bedrooms and 1.5 bathrooms, new fully equipped kitchen and nice and light living room. In the living room there is a sleepers sofa, w ....

2 Bedroom(s) 2 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach house

Captain's Quarters Spinnakers

Captain's Quarters Spinnakers: Lovely Pool Home Just 250 Steps To The Beach!

CAPTAIN'S QUARTERS SPINNAKERS COTTAGES Spinnakers Vacation Cottages, Captain's Quarters is surrounded by lush tropical landscaping, close to everything but with a feeling of being tucked away! This lovely vacation rental is located in Holmes Beach a ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Holmes Beach, FL

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Holmes Beach condo

Sunset Inn B Holmes Beach

Sunset Inn B Holmes Beach

The Sunset Inn in Holmes Beach is conveniently located on Gulf Drive. Close to shopping, dining, private and public beaches. Relax by the pool or take a short walk to the clear waters and white sandy beaches of Holmes Beach. All the conveniences of h ....

2 Bedroom(s) 1 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach house

Carissa Villa 203

Heated Pool Free WiFi & Trolley Close to Beach Sleeps 8!

The tropical landscaping surrounding this fabulous Mediterranean-style home invites you in as soon as you drive up. Enter into the luxury of Carissa Villa, and feel yourself relax. As you walk in, you will immediately notice the beautiful vaulted cei ....

3 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 8
Holmes Beach, FL

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Holmes Beach house

Buena Vista/Schoene Aussicht

Our Waterfront Home Is All Ready Just For You!

This is the Florida view you have been dreaming of... Single family home situated at the end of a natural canal with a view over the water. Sit outside, fish off our dock, take out the kayaks, or just walk steps across the street to the beach! If yo ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
Holmes Beach, FL

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Holmes Beach house

Vacation Home

Holmes Beach Family Home w/Private Pool & 3 Decks!

Explore Florida’s beautiful Anna Maria Island from ‘Salty Dogs Beach House,’ a 3-bedroom, 2.5-bathroom, single family Holmes Beach vacation rental house. With accommodations for 6, a gourmet kitchen, private backyard oasis and 2 decks overlooki ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Holmes Beach, FL

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Holmes Beach house

Standard 2 Bedroom

Mainsail Beach Inn 2 Bedroom

The stunning interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bedroom, 2.5 bathroom residences are attractively decorated, with white walls, cool pastels, local artwork, polished pine floors and comfortabl ....

2 Bedroom(s) 3 Bath(s) Vacation Rental
Holmes Beach, FL

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Holmes Beach townhome

Sandcastle

Sandcastle - Spacious home with amazing private pool - only minutes to beach!

You will love this home on Anna Maria Island. The Island is like the sleepy beach villages of long ago: no rides, no boardwalk, just a leisurely place to relax and enjoy the water, the beach, the pool and rejuvenate. This spacious 1600+ sq ft 3 story ....

2 Bedroom(s) 2 Bath(s) Townhome
Holmes Beach, FL

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Holmes Beach house

Adam's Eden

Adam's Eden - Home

Adam's Eden is less than two blocks to one of the island's best beaches. Itâ??s located right in the middle of paradise at 2917 Gulf Drive in Holmes Beach. This private home is surrounded with lush tropical plantings and trees. It has three bedrooms ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Holmes Beach, FL

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Holmes Beach condo

Palm Cay 3

Palm Cay 3 2/1 Condo Pool Near White Sandy Beach Close To Dining & Shopping

Palm Cay Condominium #3 is located at 3000 Gulf Drive in Holmes Beach, on the west side of the street for easy beach access. The complex offers a heated pool and an on-site coin operated laundry room for your convenience. It’s a short stroll to sho ....

2 Bedroom(s) 1 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach condo

The Anna Maria Island Beach Castaway 1

1BR 1BA Across Beach, FREE Breakfast, Beach Chairs and Umbrella, Walk to Eats

Located 20 Feet From The Beach Gulf Views Heated Pool One Free Breakfast Located Within A One Minute Walk Of Skinny's Where You Will Find The Islands Coldest Beer And Best Burgers FAMILY/CHILD FRIEDLY CONDOMINIUM. The Anna Maria Island Beach Castaw ....

2 Bedroom(s) 1 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach condo

Fountain Head

Stunning 2BR/2BA Condo w/ 3 Lanais Each Providing Scenic Views of the Gulf

Fountainhead Condo #3, located at 3402 6th Avenue in Holmes Beach is just a few steps from the beautiful beaches and emerald green water of the Gulf. This eight unit complex has a heated pool and laundry room on site. Due to some long awaited tree re ....

2 Bedroom(s) 2 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach house

TURTLE TURF 519

TURTLE TURF BEAUTIFUL 3 BEDROOM 3 BATH PRIVATE PET FRIENDLY POOL HOUSE

BEAUTIFUL 3 BEDROOM PET FRIENDLY CANAL HOME W/Boat Dock& Lift offers a SPACIOUS 3 bedroom, 3 bath with a heated pool. King in the master, queen in the guest room and two Bunk beds in the third room. Enjoy life in the heart of Anna Maria. Enclose ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Holmes Beach, FL

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Holmes Beach condo

Vacation Home

Gulf Sands 201: 2 BR / 2 BA condo in Holmes Beach, Sleeps 6

VRC16-000492 Gulfsands Condo #201, located at 4200 Gulf Drive in Holmes Beach, is a beautifully furnished two bedroom, two bath condo directly on the beach. It’s in a popular Gulf front complex with a large heated pool, elevator and undercover par ....

2 Bedroom(s) 2 Bath(s) Condo
Holmes Beach, FL

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Holmes Beach house

Four Beach Lovers 1

Four Beach Lovers 1 Walk Out Your Front Door And Your Toes Will Meet The Sand

VRC16-000516 Welcome to the Four Beach Lovers, located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnis ....

1 Bedroom(s) 1 Bath(s) Vacation Rental
Holmes Beach, FL

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Find Affordable Holmes Beach Hotels & Vacation Rentals by Owner

Plan your Holmes Beach Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Holmes Beach, Florida. Our Vacation Rentals by Owner, including Pet Friendly Rentals, let you get the most from your vacation in Anna Maria Island.

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