Holiday rentals with a pool in Holmes Beach

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Top-rated rentals with a pool in Holmes Beach

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

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Guest favourite

Apartment in Holmes Beach

4.99 out of 5 average rating, 125 reviews

Beach Escape - Make Memories on Anna Maria Island!

Relax and unwind at this updated beach condo with a heated pool and outdoor shower overlooking a peaceful park. Very short stroll through the park and then about 150 steps to the white sand beach. Quaint condo community with only 8 units total. Wonderful couple escape or family getaway. Sleeps 2-6 guests. Private, covered 2 car parking. Laundry in unit. Storage room with beach wagon, beach chairs, and Weber grill. Location is a hidden gem close to everything you need for a relaxing island stay.

27 Apr – 4 May

$448 SGD per night

Guest favourite

Apartment in Holmes Beach

5.0 out of 5 average rating, 28 reviews

Lovely Beach View Condo on Anna Maria Island

Brand New Listing! Hello Sunshine...Take time and breathe again at this special and tranquil getaway. This 1 bedroom 1 bath corner unit is in a charming beachside complex with a lovely pool & gardens directly across & just 20 steps from the beautiful beaches of Anna Maria Island & the sparkling waters of the Gulf of Mexico. Great restaurants and the free island trolley are within walking distance! Relax, enjoy, and make new memories of what will soon be your favorite vacation destination.

11–18 Dec

$305 SGD per night

Guest favourite

Apartment 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.

22–29 Jun

$281 SGD per night

Guest favourite

Home in Holmes Beach

4.95 out of 5 average rating, 158 reviews

Set 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.

16–23 Aug

$449 SGD per night

Guest favourite

Flat in Holmes Beach

4.97 out of 5 average rating, 185 reviews

Crows Nest at Spinnakers Vacation Cottages

Close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love the location, the ambiance, and the high ceilings. Located in the lush tropical paradise of Spinnakers Vacation Cottages. Offers a spacious living area, with the bedroom and bathroom on the living floor with a spiral staircase leading to a loft with two twin beds. Great for couples, families and dogs (with small pet fee) Great private deck for star gazing! Spa maintains same temperature as pool

4–11 Jan

$406 SGD per night

Guest favourite

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!

31 Aug – 7 Sep

$616 SGD per night

Guest favourite

Holiday home in Holmes Beach

4.94 out of 5 average rating, 33 reviews

AMI Ohana Beach Resort C with fabulous salt pool!

The location is perfectly situated in the middle of the island with quick access to the beach (3 minute walk from door to shore without crossing Gulf Drive), Publix grocery store, Walgreens, Manatee Public Beach, shopping, restaurants and more. The free trolley stop is steps away offering an affordable way to explore the whole island. Ohana Beach Retreat is a newly renovated triplex in Holmes Beach on Anna Maria Island. Come enjoy our heated salt water pool in an oasis of palm trees.

1–8 Dec

$436 SGD per night

Guest favourite

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.

11–18 Dec

$397 SGD per night

Guest favourite

Home in Holmes Beach

4.97 out of 5 average rating, 32 reviews

Unit B updated 2/2 Shared pool! Walk to beach

Spacious, and completely updated, ground floor 2/2 with a private patio. Unit B is approx 1200 sq ft and part of a duplex. Guests who book this unit will have access to a brand new heated pool and jacuzzi shared with only 3 other units. The unit is super close to the beach, trolley and wonderful things AMI has to offer!! The entire unit has been updated with Brand new appliances, furniture, and bedding throughout the home. Super walkable to several restaurants and shops.

3–10 Dec

$325 SGD per night

Guest favourite

Townhouse in Holmes Beach

4.95 out of 5 average rating, 78 reviews

Family friendly condo in Holmes Beach

This light-filled condo is just over 2 blocks to the sugary sand and turquoise water of the Gulf of Mexico, and an easy walk to the shared heated pool! Not only is this townhouse-style condo well-maintained, but you will find an updated beachy style perfect for your getaway. Walk, bike or hop on the nearby (free) trolley and find boutique shopping, sightseeing and a large selection of locally-owned restaurants throughout Anna Maria, Holmes Beach and Bradenton Beach.

6–13 Dec

$429 SGD per night

Guest favourite

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.

20–27 Jul

$150 SGD per night

Guest favourite

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.

16–23 Dec

$606 SGD per night