Vacation 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 favorite

Condo 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.

Apr 20 – 27

ﺩ.ﺇ1,407 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 18 – 25

ﺩ.ﺇ1,047 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.

Dec 21 – 28

ﺩ.ﺇ891 per night

Guest favorite

Apartment 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

Aug 10 – 17

ﺩ.ﺇ1,128 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.

Dec 7 – 14

ﺩ.ﺇ1,937 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

ﺩ.ﺇ1,704 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!

Oct 1 – 8

ﺩ.ﺇ611 per night

Guest favorite

Bungalow in Anna Maria

4.88 out of 5 average rating, 121 reviews

Bay Breeze Cottages #2

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.

Dec 8 – 15

ﺩ.ﺇ1,104 per night

Guest favorite

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.

Dec 9 – 16

ﺩ.ﺇ1,193 per night

Guest favorite

Condo in Holmes Beach

4.96 out of 5 average rating, 116 reviews

Beautiful beachfront condo for perfect vacation

Beautiful, cozy, elegantly furnished, spacious (1350 sqf with a large terrace), beachfront, 2 bedroom - 2 bathroom condominium, in the best managed, boutique-style gulf front residential complex on Anna Maria Island in Florida for an ideal vacation. Heated pool and hot tub, 2 tennis courts, 2 elevators, top floor unit, high speed internet, washer/dryer in unit, beach chairs, close to supermarket (Publix) and restaurants, free island trolley, rich cultural life.

Jul 20 – 27

ﺩ.ﺇ960 per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 187 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 16 – 23

ﺩ.ﺇ442 per night

Guest favorite

Townhouse in Holmes Beach

5.0 out of 5 average rating, 124 reviews

Relax & Unwind! Beautiful home 700 ft from beach!

Beautiful home less than 2 blocks from the beach! Well-appointed 3 bedroom home with modern decor in quiet beach community. Shared heated pool and less than 5 minute walk to the powder white sand beaches of Anna Maria Island! Perfect house for families. Saturday to Saturday rental only during peak season (Jan-Aug). 7 night minimum due to city ordinance .

Dec 28 – Jan 4

ﺩ.ﺇ1,651 per night