Your dates are popular!% of our inventory is booked.Book Now!
105 properties returned
Sort by:Random
Name
Beds
Beds
Sleeps
Sleeps
Random
Price
Price
When looking to accommodate a large group during your paradise Anna Maria Island vacation look no further than “Catchin’ Rays”. This fun four bedroom, four bathroom Holmes Beach vacation rental spaciously sleeps up to 8 guests in comfort and style. After spending a week at this fabulous Holmes Beach vacation rental home within walking distance to t
Beautiful, spacious, and accommodating; all words that suit Coral Castle. A gorgeous 5 bedroom/3.5 bath rental home is stunning and packed with incredible amenities. A hot tub, a dock, heated pool, and only a 3-minute walk away from the beach just to name a few! Now you can also bring along your fur babies - limit two dogs up to 25lbs each. The fee
“Sea Glass” is a lovely ground level 3 bedroom 2 bathroom duplex style Holmes Beach vacation rental home suited for up to 6 vacationers. Plenty of space for everyone, this rental home has 1 king bed, 1 queen bed, a Twin over Full Bunk, a Twin bed, and a queen sleeper sofa. Spacious, but not too big, “Sea Glass” is sophistication without pretension.
Harrington Cottage is an adorable Anna Maria beach cottage that’s so close to the Gulf of Mexico you can practically smell the sea salt air! Less than a block away you’ll find the white sand beaches of Anna Maria Island, all while staying in this cute 4 bedroom, 3 bath cottage. Enjoy the peace and quiet afforded by the city of Holmes Beach. Harring
A comfortable stay with a peekaboo view of the Gulf of Mexico, private pool, and rooftop deck included!With a recently updated kitchen, this Holmes Beach property is decorated with a beach cottage style, giving it a relaxing vibe that you’re sure to enjoy. This island getaway is only a few steps away from the beach, just a little jaunt across Gulf
GONE COASTAL at FOUNTAINHEAD CONDOMINIUMS - Accommodating up to four guests for a fun laid back beach vacation, Fountainhead Unit 2 offers the perfect two bedroom, two bathroom getaway for you and your family. Centrally located on Anna Maria Island, Fountainhead Unit 2 is near everything for an entertaining stay including gulf beaches, free trolley
Upon arriving at Hidden Oasis, you’ll notice a stand-alone duplex with a blue exterior that beautifully matches the colors of the Gulf. There is a large driveway space, a two-car garage (for owner use only), and views from the covered balcony on the home’s second floor. The back patio is also owner use only, but your elevated balcony has the best v
Blue Lagoon 3 “Egret” has everything you’ll need for a fun Anna Maria Island paradise vacation. This two bedroom and two bathroom Key West style Holmes Beach vacation rental condo offers accommodations for up to six guests with one king bed, two twin beds and a queen sleeper sofa. <br /><br />When you arrive at Blue Lagoon 3 “Egret” you are greete
“Promise kept” is located in Holmes Beach on Anna Maria Island. This property has been renovated to feature some of the original characteristics of the vintage home. One stay here, and your promise will be kept to return again and again. Now dog friendly with 1 dog up to 25lbs.<br /><br />This beautiful ground level home has 3 bedrooms and 2 bathr
“EverLasting Sunsets B” is the perfect Anna Maria Island beach rental for a relaxed Florida getaway. When you arrive at this unit you’ll be greeted with a lush tropical landscaping letting you know your vacation has begun!<br /><br /> During your visit you’ll be less than a block from the Gulf of Mexico beaches and endless Florida sunshine! This du
The perfect spot for an extended island getaway, 523 Loquat is a stunning three bedroom, 3 full bathrooms, canal front Anna Maria Island vacation rental home with accommodations for up 6 guests in casual island style luxury. <br /><br />523 Loquat is located in a coveted vacation destination in the city of Anna Maria just a short walk to Pine Avenu
Holmes Beach is a quaint and salty beach town with tons of character. From perfect beaches to great dining and nightlife, this destination is sure to please. “The Villas 3B” is a few blocks north from Holmes Beach city center. Here is where you’ll find many things to do within a short walk. The complex offers a shared free dryer and coin-op washer.