Vacation rentals with a pool in Anna Maria

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Top-rated rentals with a pool in Anna Maria

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Anna Maria

4.93 out of 5 average rating, 153 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!

Dec 7 – 14

R10,085 ZAR per night

Guest favorite

Home in Holmes Beach

4.95 out of 5 average rating, 158 reviews

Sea AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Oct 13 – 20

R5,559 ZAR per night

Guest favorite

Condo in Holmes Beach

4.98 out of 5 average rating, 108 reviews

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean and comfortable, my unit at Sandy Pointe II is in a secluded setting just a few minutes walk to a less crowded, quieter section of beautiful AMI beach. From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! A FREE Island trolly stop is steps from our entrance with grocery, drug store, beach shops and so much more just across E Bay Dr.

Jun 22 – 29

R3,947 ZAR per night

Guest favorite

Home in Bradenton Beach

4.97 out of 5 average rating, 153 reviews

Paradise! Steps2 Private Beach & Tropical Yard!

Less than a 2 minute WALK from the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. With large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with a bathroom on opposite ends of the house (a pocket door adds privacy). Private heated salt water pool sits amidst the lush tropical yard. Hop on the free A/C'ed trolley and explore Florida's gorgeous Anna Maria Island.

Apr 26 – May 3

R13,043 ZAR per night

Guest favorite

Home in Holmes Beach

4.97 out of 5 average rating, 124 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly (to 35 lbs) in a great location 5 min. walk to the beach. Private lagoon-style *heated* pool amid lush landscaping with gorgeous rock waterfall. Fully updated kitchen, 60-inch Sony HDTV, 55'' Samsung Frame TV, Italian leather reclining sofas, BBQ, beach gear, updated bathrooms, three king bedrooms. Classic Florida one-level home - no stairs. Managed directly by owners. No crazy fees!

Aug 31 – Sep 7

R8,696 ZAR per night

Guest favorite

Condo in Bradenton Beach

5.0 out of 5 average rating, 17 reviews

AMI Perfect Experience

This condo has been designated as a Guest Favorite. This beautiful ground floor condo offers the best experience and perfect vacation getaway in Anna Maria Island for up to 4 guests. Located steps from the beach, this condo has exceptional value with its amenities, including the largest heated pool on the island, tennis courts, pickleball, bocce ball, workout room, beach chairs, umbrella, noodles, and wagon for those looking to stay active. It has everything you need including location!

Dec 9 – 16

R3,093 ZAR per night

Guest favorite

Condo in Holmes Beach

4.92 out of 5 average rating, 83 reviews

Spacious renovated 2-bdrm a short walk from beach

You will love our large upscale, 3rd-floor condo overlooking a nature reserve and swimming pool, 3 blocks from beautiful Anna Maria Island beach, with 2 bedrooms and 2 bathrooms (both ensuites). This well-maintained rental has recently been renovated and includes heated swimming pool access, ensuite washer/dryer, dishwasher, WiFi & cable. It sleeps 4 comfortably, with a sofa bed for up to 2 temporary visitors, and has free parking. This unit is very clean, non-smoking and pet free.

Sep 21 – 28

R2,550 ZAR per night

Guest favorite

Bungalow in Anna Maria

4.88 out of 5 average rating, 121 reviews

Bay Breeze Cottages #2 (The Redfish)

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Apr 25 – May 2

R7,624 ZAR per night

Guest favorite

Home in Anna Maria

4.99 out of 5 average rating, 78 reviews

CHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B

Location! North end of Anna Maria Island . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends. Steps to the Bean Point Beach . Includes beach chairs, umbrellas and all you need for a perfect day at the beach! Heated pool , private seating, grilling areas, bicycles and much more available. MAX Occupancy 4 people including children of any age.

Jan 14 – 21

R8,941 ZAR per night

Superhost

Home in Bradenton

4.85 out of 5 average rating, 20 reviews

"Paradise" by the Private (Heated) Pool light!

Perfect Couple's Getaway "Paradise" with Private Heated Pool in Very Secluded Tropical Backyard! Large Screened in Lanai, BBQ Grill, Bonus Outdoor Shower, Lounge Chairs, Washer & Dryer, Wi-Fi, Smart TV, Queen Bed, Kitchenette (comes complete with everything you need to cook, make coffee, etc.), Mini Fridge/Freezer, Breakfast Bar with Seating for Two, Updated Bathroom. Located 1 Mile from the Beautiful Gulf Coast and Beaches.

Aug 23 – 30

R2,714 ZAR per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 188 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Jul 21 – 28

R2,116 ZAR per night

Guest favorite

Cottage in Anna Maria

4.98 out of 5 average rating, 208 reviews

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Apr 12 – 19

R7,874 ZAR per night