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Best Pool Vacation Rentals on Anna Maria Island

When you search for vacation rentals on Anna Maria Island, is a pool at the top of your must-have list? Choose Breezy Beach, Palm Villa, It’s My Dream, Ocean Breeze or Beach Daisy to get the best vacation rentals with a pool. These are the top 5 pool rentals with Florida Dreams. Visitors return yearly to these Anna Maria Island vacation rentals for their proximity to the beaches, quiet neighborhoods, and amazing pools. Which one will be perfect for your family?

Breezy Beach

Breezy Beach is located in the heart of Holmes Beach, close to restaurants, shops and the free Island trolley that runs up and down the Island all day. On the outside, you will enjoy a private pool with spa, a covered lanai, gas BBQ grill, and tropical landscaping. Pets are welcome for an extra fee!

This charmer has a fantastic pool with a sunning deck where shallow water is perfect for little ones to play while adults enjoy the deeper areas or the jetted hot tub. Your family can enjoy sunny Florida days under the covered areas or on the screened porch with amazing views of the canal and pool area. Three of the four bedrooms each have a bathroom and a king-size bed, while the fourth bedroom has a bunk bed. This home sleeps, 8 people. Modern appliances, free WiFi, and chairs – everything is included in the Breezy Beach home.

Palm Villa

Palm Villa is a New England style cottage and Florida Keys getaway all rolled into one. The vaulted main room ceiling gives this newly constructed home a wide-open feel while the shabby chic furnishings create a cozy atmosphere. The tropical foliage around the heated pool creates a private oasis

One of the best pool rentals on Anna Maria Island – the Palm Villa is a 3br/3bath home with a stunning pool that includes a rock waterfall feature, built-in seating and a table (drinks in the pool anyone?) and a shallow-water sunning ledge. Inside, guests will love the stainless steel, big-screen TVs and upscale finishes of the living and dining areas. Two master bedrooms with en-suites and a third bedroom with a full bath make it easy for six people to sleep comfortably. The beach is 5-minutes away and beach towels and toys are provided. Palm Villa is also a pet-friendly rental.

Ocean Breeze

This vacation beach home duplex provides every luxury you'll need to make the most of your Florida Dreams vacation. This cozy, but spacious, coastal cottage sleeps 8. Ocean Breeze provides an outdoor oasis with a private pool and spa, large patios, and tropical landscaping. The kitchen is fully equipped or use the outdoor grill and enjoy your meals al fresco on the covered patio. It's a short walk to the famous soft, white, sandy beaches of Anna Maria Island.

One of the larger vacation rentals on Anna Maria Island, Ocean Breeze has 4br/3baths and plenty of room to relax with large, sunny bedrooms and lots of outdoor living space. Have wine and cheese while chatting with friends in the pool – the built-in table and twin ledge seating are perfect for winding down Florida-style. The covered patio has a grill, a table for eight, and loungers to soak up the sun after a great dinner al fresco. The soft sands of the beach are just a few minutes away from this gorgeous home.

Beach Daisy

This impeccable beach house is located in Holmes Beach on Anna Maria Island with countless activities to choose from. In addition to the obvious strolls along our fabulous beaches, you can take scooters or bicycles to explore the island, enjoy a kayak eco-tour, eat at one of our famous piers, charter a sport fishing trip, or picnic while watching our exquisite sunsets.

See the Gulf of Mexico from the master suite and guestroom of Beach Daisy, one of the best pool rentals on Anna Maria Island. A massive pool, a grill the size of your kitchen back home and plenty of outdoor seating make this home the perfect spot to gather your family together for al fresco meals before you head out to explore the island or play on the beach. Inside, the open concept kitchen-living area flows out onto an upstairs deck with plenty of places to sit and talk, play poker on the game table or watch the flat screen TV before heading to bed.

It’s My Dream

It's My Dream is a brand new and lovely island-themed private duplex with 3 bedrooms and 2 bathrooms. Equipped with a private heated pool/spa and spacious deck. This home truly represents the best of what Anna Maria Island has to offer. Centrally located with just a short 2-minute walk away from the beaches and close to all of the local shops and boutiques!

This brand new house is filled with cozy luxury like:

  • High-quality bedding
  • Luxury finishes
  • Granite counters
  • HDTV’s
  • Heated Pool/Spa
  • Free WiFi
  • 2-minute walk to beach

The heated pool/spa has a shallow water area, a table with plenty of seating, and a spacious deck with lots of loungers surrounding it. Inside, there are two king beds and a queen bed, comfy furnishings, and a large dining table make it easy to get together for a meal. Views from the upper deck are amazing in It’s My Dream.