
Holiday 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.

Green Jacaranda AMI Duplex B, 5 min walk to beach
Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

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.

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

AMI Sunset~Close to beach! Heated Pool!
A charming three-bed, two-bath beach house on Anna Maria Island, this coastal retreat offers a heated pool, two king rooms, and a fun bunk room. Just steps from the beach, it delivers unforgettable sunrises and sunsets. Beautifully designed for comfort and relaxation, it’s the perfect island getaway for families or friends looking to enjoy the best of AMI. Enjoy your beach days with ease. We supply beach towels, comfortable chairs, and a wagon to make your trips to the shore effortless.

Salty Harbor AMI pool retreat near the Beach
Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

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 .

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

83rd St Villas East by Duncan Real Estate
Welcome to The 83rd St Villas East! 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 Caf appliances, ample counter space, cook top and oven, extra-large fridge/freezer making meal prep a breeze.

Heated Pool, Steps to the Beach, Luxury Home
Welcome to your Anna Maria escape! Our 3-bed luxury home features a heated, private pool and is just minutes from the sugar-sand beach. • Spacious open-plan living & gourmet kitchen • Three serene bedrooms with premium linens • Outdoor lounge, grill & sun loungers • Fast Wi-Fi, smart TVs, washer & dryer • Beach chairs, and essentials • Superhost service ensures rapid replies and spotless cleanliness Book now and start making island memories!

Beachfront Paradise! Ground level with Heated pool
Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!

A Coastal Retreat Steps From the Sea
Just a short walk to the sugary sands of Holmes Beach! This recently updated condominium has everything you need to enjoy a true getaway. Grab our beach chairs, umbrella, coolers, toys, and amazing beach cart to effortlessly pull the beach necessities across the sand. After a nice float in the ocean, come back to the tropical setting surrounding our heated pool. Welcome to Island Life.

Fanta Sea | Island Fun w/Pool, Hot Tub, Game Room!
Get ready for laid-back luxury! This fun and breezy 4-bedroom, 2.5-bath Holmes Beach retreat has everything you need for an unforgettable island escape. Relax by the tropical pool and built-in hot tub, challenge your crew to a board game or ping pong in the game room, or unwind on one of three covered balconies with comfy seating.
Popular amenities for Holmes Beach rentals with a pool
House rentals with a pool

Cozy Cottage - POOL HOME! 3/3

Bayfront Beach access with Heated Pool!

Dolphin Resort | Pool, Spa, Game Room & Beach

Sailfish Bungalow. Perfect for your family vacatio

Ocean Air Oasis-New Centrally Located AMI Luxury

Private Luxurious Ground Level Home

Unwind Sunshine: steps to locals' favorite beach

New! Resort-Style Pool + Hot Tub + Beaches + IMG!
Condo rentals with a pool

Steps from the beach

Luxury 3/3 Margaritaville Resort

Beach Escape & Pool, steps to Beach & restaurants

Sunset and beach view from your balcony Unit 403

Sun-Kissed Memories!

Steps to the beach! Condo with pool at The Terrace

Shorewalk full condo IMG Beaches Anna Maria

Beachy Chic! 1st Floor Condo-Pool-Close to Beach
Other holiday rentals with a pool

Backyard Bliss Anna Maria Island

Coastal Luxe Villa! Near AMI

Getaway Family Beach Townhome w/Pool!

Close to the Beach+ Private heated pool and spa!

1 Block to Beach ~ 3BR Coastal Retreat with Pool

Anna Maria Island-just a few steps to the beach

Seaquel: A Tropical Retreat - Private Pool Home

Walk to Gulf: Luxe Luau-Themed Gem in Holmes Beach
When is the best time to visit Holmes Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $494 NZD | $626 NZD | $814 NZD | $652 NZD | $537 NZD | $611 NZD | $626 NZD | $522 NZD | $471 NZD | $430 NZD | $492 NZD | $522 NZD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about holiday rentals with a pool in Holmes Beach

Total holiday rentals
Explore 1,150 holiday rentals in Holmes Beach

Nightly prices starting at
Holmes Beach holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 14,600 verified reviews to help you choose

Family-friendly holiday rentals
1,020 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 370 rentals that welcome pets

Rentals with dedicated workspaces
610 properties have a dedicated workspace

Wi-Fi availability
1,140 of Holmes Beach holiday 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!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Rentals with a fire pit Holmes Beach
- Townhouse rentals Holmes Beach
- Pet-friendly rentals Holmes Beach
- Villa rentals Holmes Beach
- Rentals with a kayak Holmes Beach
- Rentals with outdoor seating Holmes Beach
- Beachfront rentals Holmes Beach
- Cottage rentals Holmes Beach
- Rentals with a fireplace Holmes Beach
- Rentals with a patio Holmes Beach
- Rentals with a hot tub Holmes Beach
- Beach condo rentals Holmes Beach
- Luxury rentals Holmes Beach
- Beach house rentals Holmes Beach
- Rentals with an EV charger Holmes Beach
- Rentals with a washing machine and dryer Holmes Beach
- Apartment rentals Holmes Beach
- Waterfront rentals Holmes Beach
- House rentals Holmes Beach
- Rentals with beach access Holmes Beach
- Fitness-friendly rentals Holmes Beach
- Rentals with lake access Holmes Beach
- Resort rentals Holmes Beach
- Condo rentals Holmes Beach
- Family-friendly rentals Holmes Beach
- Rentals with pools Manatee County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Coquina Beach
- Turtle Beach
- Vinoy Park
- Lido Key Beach
- Caspersen Beach
- Amalie Arena
- Dunedin Beach
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- Hard Rock Casino
- Manasota Key Beach
- River Strand Golf and Country Club
- Tampa Convention Center
- North Beach At Fort DeSoto Park




