- 69 properties returned
-
Sort by:
Random
- Name
- Beds
- Beds
- Sleeps
- Sleeps
- Random
- Price
-
Experience Island Living at Waters Edge 208S, an exquisite, newly remodeled condo located just a short stroll from the serene shores of Anna Maria Island. Whether you're drawn to the beach for sunbathing, water sports, or peaceful relaxation, this charming property has it all. With easy beach access, a shared heated pool, and local shops and restau
Waters Edge 208S
Condominium- 2
- 2 2
- Pool
- No Pets
- Sleeps 6
- 17 Views
-
Anna Maria Island vacation rental home “EverLasting Sunsets A and B” is a fabulous ground level duplex perfect for any family getaway. Enjoy 3 bedrooms and 2 bathrooms with 2 king beds and 1 queen bed providing everyone space for a comfortable vacation.<br /><br />With separate units “EverLasting Sunsets A&B” is a great way to vacation with fam
EverLasting Sunsets AB
Home- 3
- 3 3
- Pool
- No Pets
- Sleeps 8
- 11 Views
-
Charming cottage-style condo w/ shared pool, Gulf views and easy beach access!<br /><br />Vacation in style with this charming cottage-style condo on Anna Maria Island. Featuring a shared pool, Gulf views from the balcony, and easy access to gorgeous beaches, this condo is perfect for a couple of friends or a romantic retreat. Wake up to the sun st
Palm Isle Village 3210
Condominium- 1
- 1 1
- Pool
- No Pets
- Sleeps 4
- 10 Views
-
Welcome to Appletini, a fully renovated vacation rental in Holmes Beach designed for travelers seeking comfort, style, and the ultimate Anna Maria Island experience. Situated just minutes from the beach, this beautifully updated duplex combines modern coastal elegance with an unbeatable island location.Inside, you'll find professionally curated des
Appletini
Multi-Family- 2
- 2 2
- Pool
- No Pets
- Sleeps 6
- 66 Views
-
“Palms Beach West” on Gulf Drive is where Anna Maria Island vacations become lifetime memories! This beautiful Holmes Beach vacation rental home provides accommodations for up to 6 guests including 3 Bedrooms, 2 Bathrooms with 1 King bed, 1 Queen bed, and 2 Twin beds. <br /><br />Located a short walk away from a pristine gulf beach access 3700 bloc
Palms Beach West
Multi-Family- 3
- 2 2
- Pool
- No Pets
- Sleeps 6
- 7 Views
-
Discover the revitalized charm of Coconuts Beach Resort 101, a newly remodeled ground-level condo located in the heart of Holmes Beach on Anna Maria Island. This one-bedroom, one-bathroom retreat has been given a complete makeover, offering a clean, modern aesthetic with inviting coastal touches. Comfortably accommodating up to four guests, this po
Coconuts 101
Condominium- 1
- 1 1
- Pool
- No Pets
- Sleeps 4
- 21 Views
-
Welcome to your Anna Maria Island escape "Pineapple Paradise"! New to the vacation rental market, this beautifully designed 4-bedroom, 5-bathroom home in Holmes Beach is just two blocks from the beach—perfect for families and groups ready to enjoy sun, sand, and relaxation."Pineapple Paradise" is a spacious two-level home offers plenty of room to s
Pineapple Paradise
Home- 4
- 5 5
- Pool
- No Pets
- Sleeps 8
- 21 Views
-
Gulf View Cottage is a charming, recently renovated home with a rooftop deck offering sweeping views of the Gulf. Relax and enjoy the private, heated pool while experiencing the ultimate Florida vacation!As you arrive at Gulf View Cottage, you'll notice its unique shape, spacious driveway, and beautiful tropical plants in the front yard. Step insid
Gulf View Cottage
Home- 4
- 4 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 25 Views
-
Experience the Tropical beach paradise vacation of a lifetime when you stay at Holmes Beach vacation rental condominium “Vista Grande Sul Mar”. This gorgeous beach front condo, located within the Vista Grande complex, rooms up to 6 guests with 1 king bed, 1 queen bed and 2 twin beds in this 3 bedroom 3 bathroom spacious vacation destination.<br /><
Vista Grande 1 Sul Mare
Condominium- 3
- 3 3
- Pool
- No Pets
- Sleeps 6
- 24 Views
-
Staying at Buena Vista unit 4 is a fun and memorable experience. Including comfortable furniture, smart televisions in all rooms with HBO and Showtime, and a custom chefs kitchen with induction stove as well as a double door wine fridge; vacationers love celebrating their stay in the spacious living room perfect for entertaining. The open floor pla
Buena Vista 4
Condominium- 4
- 4 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 20 Views
-
Experience relaxed waterfront living at this beautifully renovated bayfront home in the prestigious Key Royale neighborhood of Anna Maria Island. This charming ground-level 2-bedroom, 2-bath vacation rental combines modern coastal design with peaceful island ambiance, offering everything needed for an unforgettable monthly getaway.Perfectly positio
By the Bay
Home- 2
- 2 2
- Pool
- No Pets
- Sleeps 4
- 11 Views
Waters Edge 208S
Experience Island Living at Waters Edge 208S, an exquisite, newly remodeled condo located just a short stroll from the serene shores of Anna Maria Isl
5
Adam F
5
Patrick B
5
Brittany T
5
Kenneth B
5
Krystal R
5
Jennifer H
EverLasting Sunsets AB
Anna Maria Island vacation rental home “EverLasting Sunsets A and B” is a fabulous ground level duplex perfect for any family getaway. Enjoy 3 bedroom
5
Jared T
Palm Isle Village 3210
Charming cottage-style condo w/ shared pool, Gulf views and easy beach access!
Vacation in style with this charming cottage-style condo on
Vacation in style with this charming cottage-style condo on
5
Carlanan R
5
Lisa B
5
Donna S
Appletini
Welcome to Appletini, a fully renovated vacation rental in Holmes Beach designed for travelers seeking comfort, style, and the ultimate Anna Maria Isl
5
Pamela B
5
Tina & Steve L
5
Karen J
5
null
5
Suzanne C
5
keith S
5
Anonymous U
5
Audrey M
5
Michael S
5
Suzanne C
5
Dawn S
5
Deb B
5
Katie M
Palms Beach West
“Palms Beach West” on Gulf Drive is where Anna Maria Island vacations become lifetime memories! This beautiful Holmes Beach vacation rental home provi
5
Deborah H
5
Taylor P
5
Brenda R
5
Holly T
5
Steve S
5
Stephanie L
5
Jaci H
5
Christine H
5
Jonathan L
5
Robin K
5
Kelly K
Coconuts 101
Discover the revitalized charm of Coconuts Beach Resort 101, a newly remodeled ground-level condo located in the heart of Holmes Beach on Anna Maria I
5
Barbie C
5
Jacqueline B
5
Bob and Debby G
5
Beth M
5
Kathy C
5
Kathryn C
Pineapple Paradise
Welcome to your Anna Maria Island escape "Pineapple Paradise"! New to the vacation rental market, this beautifully designed 4-bedroom, 5-bathroom home
5
Jason S
Gulf View Cottage
Gulf View Cottage is a charming, recently renovated home with a rooftop deck offering sweeping views of the Gulf. Relax and enjoy the private, heated
5
Tammy W
5
Kathy S
5
Stephanie K
5
Kara M
5
Melinda W
Vista Grande 1 Sul Mare
Experience the Tropical beach paradise vacation of a lifetime when you stay at Holmes Beach vacation rental condominium “Vista Grande Sul Mar”. This g
5
Kristi D
5
Dooris M
5
Dave R
5
Dave R
5
Tina E
5
Eric S
Buena Vista 4
Staying at Buena Vista unit 4 is a fun and memorable experience. Including comfortable furniture, smart televisions in all rooms with HBO and Showtime
5
Lynn L
5
Anita Z
5
Jennifer
5
Jane J
5
Amanda T
5
Kammie L
5
Daniel C
5
Jennifer M
Hidden Cove 3
Located directly on the Gulf of Mexico beach, “Hidden Cove” is a beautiful beachfront Holmes Beach vacation rental condo perfect for 4 guests! Well eq
5
Karen
5
C K
5
Donald W
5
Kathleen K
5
Randy T
5
Donald W
5
Donald B
Holmes Beach Vacation Rentals on Anna Maria Island
Holmes Beach Vacation Rentals
Holmes Beach is a small beach town on Anna Maria Island with that charming Old Florida Town feel that vacationers crave. Holmes Beach is a year-round vacation destination with some of the best sunsets anywhere in the country. There’s miles of soft, white, sandy beaches to explore and gorgeous emerald green water to swim in. With around 5,000 residents, Holmes Beach is the largest of the three communities that make up Anna Maria Island. We've got your next vacation covered with our selection of luxury Holmes Beach vacation rentals!
You’ll find the perfect Holmes Beach vacation rental at Island Real. Whether you’re looking for a luxury home or condo rental, our collection of Holmes Beach rentals has something for everyone! Our Holmes Beach vacation rental options include rentals with private pools, beach access, multifamily homes + more! Check it out and book your Holmes Beach rental today.
Check out our favorite things to do in Holmes Beach, read our “Top 10” guides, and more on our blog!