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Vacation rentals with a pool in Holmes Beach

Find and book unique homes with a pool on Airbnb

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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Top guest favorite
A private, heated pool is surrounded by tropical landscaping, featuring palm trees and lush greenery. The pool area is complemented by a brick patio, sun loungers, and a shaded table under an umbrella, inviting relaxation in a serene outdoor setting.
Home in Holmes Beach
5 out of 5 average rating, 37 reviews

Aqua Beach

Private, heated pool and newly renovated 2 bed 2 bath, upscale retreat on a quiet, peaceful island street, 300 steps from the beach. Tucked away on the east side of our elevated home "Aqua Beach Retreat Villa” with covered parking, a porch that overlooks your own private pool (for use by this rental suite only) Kitchen and bath were all upgraded and have a nice beachy feel. Great location, minutes from the beach, free island trolley, a dozen restaurants within half a mile and lots of shopping.

Guest favorite
A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.
Home in Holmes Beach
4.96 out of 5 average rating, 200 reviews

Be an 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.

Top guest favorite
A clear blue pool is surrounded by palm trees and a well-maintained patio area. Lounge chairs are arranged nearby, and a dining set is visible in the background, enhancing the outdoor space. The sun-filled setting creates a vibrant atmosphere.
Apartment in Holmes Beach
4.97 out of 5 average rating, 198 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

Guest favorite
Home in Holmes Beach
4.88 out of 5 average rating, 8 reviews

Beautiful ground level home with heated pool!

Discover your perfect getaway at this charming vacation rental in Holmes Beach, Florida. Nestled just a short walk from the pristine sandy shores, this bright and airy home features a spacious open floor plan ideal for family gatherings. Enjoy the sun in your private pool or relax on the patio surrounded by lush landscaping. The fully equipped kitchen makes meal prep a breeze, while nearby restaurants and shops offer local flavor. Experience the ultimate beach retreat in this coastal paradise!

Guest favorite
Home in Holmes Beach
4.73 out of 5 average rating, 26 reviews

Recover by the Seas at Solace East - prvt pool

The holidays are over and it’s time to recover and recharge. Escape the cold and step into island time, where quiet streets, warm sunshine, and gentle ocean breezes set the pace. We are just steps from the beach featuring a private pool perfect for slow mornings and laid-back afternoons. Enjoy Anna Maria Island, from cruising the FREE trolley to exploring charming local spots, then retreat back to your peaceful getaway. The perfect place to unwind, reset, and soak up the best of island life.

Guest favorite
Home in Holmes Beach
5 out of 5 average rating, 6 reviews

Anna Maria retreat house

Elevated home with all the amenities. Walking distance to the beach, chairs and towels provided. Relax in the backyard patio, including pool with waterfall . The shaded balcony overlooks the pool if you need to escape the sunshine. There’s a free trolley that runs all day in AMI if you don’t want to take the car out. The house is located across the street from Bimini Bay, enjoy a jog through these side streets in the morning. Local shops and restaurants that will not disappoint .

Guest favorite
Home in Holmes Beach
4.93 out of 5 average rating, 124 reviews

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated PRIVATE pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

Top guest favorite
The outdoor area features a heated pool with a rock waterfall, surrounded by lounge chairs. A thatched Tiki hut provides shaded seating, set within tropical landscaping. The villa's light blue exterior and white furnishings enhance the inviting atmosphere of the space.
Condo in Holmes Beach
4.94 out of 5 average rating, 154 reviews

Blanco and Sunset Villas on Anna Maria Island

Back Open Jan '25! Located just 200 steps from the beach you’ll have your feet in the sand in no time. A comfortable living area + fully equipped kitchen. Furnished with island décor and local art. Everything you need including a heated pool, large patio with a Tiki hut, tropical gardens, plus a private outdoor area with a shower for your comfort. Walk to everything – grocery, pharmacy, ice cream, breakfast, pizza, donuts, and the beach which is less than 2 minutes away.

Guest favorite
A private lagoon-style pool is surrounded by lush tropical landscaping. A small rock waterfall flows into the gently curved pool, which is complemented by comfortable seating. Sunlight filters through the foliage, creating a serene outdoor retreat.
Home in Holmes Beach
4.96 out of 5 average rating, 149 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 just 5 min. walk to the beach. Private lagoon-style *heated* saltwater/low chlorine pool amid lush landscaping with gorgeous rock waterfall. New appliances, HVAC, 60-inch Sony HDTV, Italian leather reclining sofas, BBQ, beach gear, three king bedrooms, all linens provided. Classic Florida one-level home - no stairs. Managed directly by owners, so no crazy fees.

Guest favorite
An outdoor view showcases a private pool surrounded by lush landscaping and tropical palm trees. The distant beach features soft white sand meeting turquoise waters. A spacious deck, complete with loungers, offers a perfect relaxation spot under clear blue skies.
Home in Holmes Beach
4.91 out of 5 average rating, 67 reviews

TOES IN THE SAND!

Waves Edge South is one of two very unique homes situated directly on the sugar white sands of Anna Maria Island. Welcome to a dreamy island which oozes the charm of ‘old’ Florida and will remind you of yesteryear when you were young and the pace was a little slower. A place where visitors and residents are as likely to use a bicycle or a golf cart as hop in a car. An Island where the warm waters will soothe your soul and you will leave longing to return once more.

Superhost
A shaded outdoor area features white sand-like gravel beneath a raised structure. Bright orange Adirondack chairs are positioned nearby, surrounded by palm trees and greenery, creating a tranquil spot for relaxation.
Home in Holmes Beach
4.73 out of 5 average rating, 41 reviews

Walk to beach | Anna Maria home w/ pool | Pets ok!

Welcome to Waves 403! This newly renovated 1,100 square feet unit offered by Tstays™ exudes inviting and embracing vibes. Its proximity to all activities guests may crave, not to mention its prime location close to the beaches, bode for nothing less than an exciting stay. Its neighborhood is calm and serene, and it's fully equipped with everything guests could want, from state-of-the-art appliances to outdoor supplies. Don't miss out on this 5-star experience!

Guest favorite
Home in Holmes Beach
5 out of 5 average rating, 5 reviews

83rd St Villas West by Duncan Real Estate

Welcome to 83rd St Villas West! A stunning ground-level vacation villa just a 6-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen with Cafe appliances, ample counter space, cook top and oven, extra-large fridge/freezer making meal prep a breeze.

Popular amenities for Holmes Beach rentals with a pool

When is the best time to visit Holmes Beach?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ1,043ﺩ.ﺇ1,322ﺩ.ﺇ1,719ﺩ.ﺇ1,377ﺩ.ﺇ1,135ﺩ.ﺇ1,289ﺩ.ﺇ1,322ﺩ.ﺇ1,102ﺩ.ﺇ995ﺩ.ﺇ907ﺩ.ﺇ1,039ﺩ.ﺇ1,102
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

Quick stats about vacation rentals with a pool in Holmes Beach

  • Total vacation rentals

    Explore 1,110 vacation rentals in Holmes Beach

  • Nightly prices starting at

    Holmes Beach vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

  • Verified guest reviews

    Over 15,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,020 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 370 rentals that welcome pets

  • Rentals with dedicated workspaces

    640 properties have a dedicated workspace

  • Wi-Fi availability

    1,100 of Holmes Beach vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Holmes Beach rentals

  • 4.8 Average rating

    Holmes Beach stays are highly rated by guests—averaging 4.8 out of 5!

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