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Holmes Beach Romantic Vacation Rentals

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    Travelers to Holmes Beach are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    21 Matching Rentals in Holmes BeachView all 511 rentals
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    Cozy Cabana West - Private Pool - Close to Beach1 / 22
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    private pool/spa beach gear1 / 34
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    The Anna Cabana Beach House is an adorable two bedroom, two bath home located at 3709 Gulf Drive in Holmes Beach. This quaint home has a large open deck with a great view of the beach. Watch the sunsets or enjoy the tropical landscaping on the large deck facing the Gulf. Numerous fruit trees and...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Internet Access
    • Hot Tub
    • Balcony
    • Grill
    • Central Heating
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Absolutely Perfect Beach House, located at 3009 Avenue F in Holmes Beach is just that – absolutely perfect! This spectacular four bedroom, three and one half bath gulf front home with an extra media room. It has its own private beach and heated pool has just been built. This beautiful home is...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Anna Cabana Bungalow #4 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a perfect complex for...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Sunbow Bay Condominium 3B located at 3701 East Bay Drive in Holmes Beach has everything you could need or want for a memorable vacation. Conveniently close to shopping and restaurants yet out of the way and quiet. Sunbow Bay offers two heated pools, tennis courts, elevators, undercover parking and...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Breakers 3, located at 103 45th Street in Holmes Beach. This luxury three-bedroom, two-bath Gulf-front beach home is located in a quiet, secluded area of Holmes Beach. The white sandy beach stretches for miles along the length of the island and spectacular Gulf vistas can be seen from the living...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Beautiful new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the heated pool in your own backyard oasis. This house has every luxury you could want, The open concept floor plan is...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sprawling 3 bed 2.5 bath LUXURY Single Family Home with HEATED pool and ELEVATOR Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind! Crosswinds Cottage is just a short five minute walk to Anna Maria Island's world renowned white sandy...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Terrace
    • Cable/satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking to go away on a romantic vacation with a special person, this 1 bedroom, 2 bath unit is perfect! It has a king size bed, jacuzzi, and is literally right on beautiful Bradenton Beach. You can look outside your window and see the blue water of the Gulf of Mexico, while watching the...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    8 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    • Patio
    • Internet Access
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The MI Happy Place Island Resort (formerly Garden Villas) is excited to be under new ownership and management, with new amenities and improvements to make a beautiful, convenient, and relaxing location even better! When renting MI Happy Place Island Resort you will have eight bedrooms and four...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Rental Home - 8 Bedrooms, 4 Bathrooms, Sleeps 22
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview If you are ready to put your 'heels in the sand', look no further. Manna-Tee Beach House is the perfect vacation spot for relaxation on Anna Maria Island. This beautiful 3 bedroom, 2.5 bath home located on Holmes Beach on Anna Maria Island has all the amenities for you. Top-of-the-line...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    609 Condord Lane - Private canal home 3 Bedroom / 2.5 Bath with private pool, maximum occupancy of 6 people. ~ Distance to the Beach: 1 mile~ Welcome to your vacation fantasy! This stunning home has been completely remodeled with top of the line amenities and a brand new pool. Decorated with...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    p class='rtejustify'>The Anna Cabana Beach House is an adorable two bedroom, two bath home located at 3709 Gulf Drive in Holmes Beach. This quaint home has a large open deck with a great view of the beach. Watch the sunsets or enjoy the tropical landscaping on the large deck facing the Gulf....
    View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The MI Happy Place  is excited to be under new ownership and management, with new amenities and improvements to make a beautiful, convenient, and relaxing location even better! When renting MI Happy Place Island Resort you will have eight bedrooms and four bathrooms sleeping twenty two making...
    View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    Rental Home - 8 Bedrooms, 4 Bathrooms, Sleeps 22
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
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    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    p class='rtejustify'>The Absolutely Perfect Beach House, located at 3009 Avenue F in Holmes Beach is just that – absolutely perfect! This spectacular four bedroom, three and one half bath gulf front home with an extra media room. It has its own private beach and heated pool has just been built....
    View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunbow Bay Condominium 3B located at 3701 East Bay Drive in Holmes Beach has everything you could need or want for a memorable vacation. Conveniently close to shopping and restaurants yet out of the way and quiet. Sunbow Bay offers two heated pools, tennis courts, elevators, undercover parking and...
    View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    p class='rtejustify'>Anna Cabana Bungalow #4 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a...
    View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have the Florida retreat of a lifetime when you book this marvelous 2-bedroom, 2-bathroom condo. The open floor plan of this unit is set up to comfortably accommodate 4 lucky guests, making it an excellent layout for a small family or several couples seeking a relaxing beach escape. Nestled near...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Ocean Views
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have the ultimate Florida getaway by escaping to this 2-bedroom, 1.5-bathroom Holmes Beach condo that comfortably sleeps up to 6 guests. Located steps away from a sandy white beach, with beautiful views of the Gulf of Mexico, you and your guests will have an unforgettable vacation here! THE...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Local time: 05:12 PM (EST)
    • Peak travel: February - April
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