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
The cottages at Palm Isle Village are some of the finest and most favored vacation properties on Anna Maria Island. We are always very proud to recommend to our vacationers, and no one can say it isn't a special place to spend quality time with friends and family. With so many indulgent, delightfully tropical features, it becomes difficult to disce
With stunning direct gulf front views, the stylish “Water's Edge 209S” is a fine example of a luxury island vacation getaway. Comfortably rooming up to 4 guests this 2 bedroom 2 bathroom Holmes Beach vacation rental condominium offers one king bed and one queen bed in a beautiful coastal inspired atmosphere. <br /><br />Situated on the Gulf of Mexi
Located on beautiful canal front property in Anna Maria City, 230 Chilson Avenue "Sand Dollar Dream" is the perfect spot for a Florida vacation with a brand new, private, heated pool and spa. Relax in spacious back yard swaying the hammock amongst the lush tropical landscaping, or roast s'mores in the fire pit seating area. This lovely renovated ho
“Summer Breeze” is one of the premier homes on the island. The perfect home for an Anna Maria Island getaway. With tropical landscaping, updated inside and out, and this rental home is stunning on all fronts. Elevated, high-end tropical décor, and pristine floors, “Summer Breeze” is love at first sight. Five large bedrooms, a spacious layout, this
When you visit Anna Maria Island vacation rental “Hop, Skip and a Beach” you are sure to have an amazing Florida getaway! Sleep up to eight guests in luxury and style. This four-bedroom rental with game room with heated pool and spa is just a short walk from the best beaches you’ll find on the gulf coast.When you enter “Hop, Skip and a Beach” you’l
"La Casa Marie" - Luxurious Gulf-Front Vacation Condo in Holmes BeachWelcome to "La Casa Marie," a stunning waterfront vacation condo situated in the picturesque La Casa Costiera complex at 7320 Gulf Drive, Holmes Beach. This exquisite 3-bedroom, 2.5-bathroom retreat can comfortably accommodate up to 6 guests, featuring a King bed, a Queen bed, and
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
Ready to find your piece of island paradise? Look no further than “Wave N’ Sea”. This beautiful, sunny Anna Maria home is a spacious three-bedroom two-bathroom rental that can accommodate up to six guests. With a new, and private, heated pool, an oversized yard with tropical landscaping, and less that two blocks from the beach, “Wave N’ Sea” is tru
"Flip Flop Oasis" Two Single Family Homes with Adjoining Yards and TWO Heated PoolsFirst Home 201 57th Street "Flip Flop Inn" If you are searching for luxury on your Island vacation, this home is your dream come true. Tucked away on a quiet street on Anna Maria Island, this Mediterranean-style Townhouse is your perfect family vacation destination.T
Perfect for a fun couple’s getaway, a casual vacation, or even a family escape. “The Villas 3A” is a one-bedroom villa that boasts a top tier location near shopping, dining, and beaches, as it’s located in the city of Holmes Beach. Able to sleep up to four guests, this unit has a welcoming and laid-back feel that’s synonymous with an island vacati
As one of the most popular beachfront accommodations on Anna Maria Island and a favorite of thousands of guests over many years, we are delighted to now have this beautifully presented and recently remodeled and creatively renovated condo under our management.Take in the unsurpassed beach view from your private balcony, and enjoy the fun art fixtur
This small quiet complex is just a two minute walk to the beautiful white sand beach. A ground level unit, find an outdoor patio with a spacious common area complete with a large heated pool, gazebo, lush tropical landscaping, and picnic tables. This makes a perfect setting for a memorable Island adventure!Casa Sierra Resort is a private Mediterran