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Holmes Beach Rentals with Pools

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1,769 apartments in Holmes Beach with pools

Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful condo, close to everything!” Everything was perfect in the condo which was new and updated! The 2 new full size beds in the 2nd bedroom were too hard. The pool was a nice size and stayed sunny most of the day. Shopping was close and the city beach also was close. We would drive down the road to our favorite stretch of the beach. I would definitely stay here again, very quiet location off the beaten path, but not far from it! Love the beach chairs, towels, cooler, umbrella, pool toys, and more provided!

Match: Swimming pool

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Price per night from

$142

Gulf Beach Place - Just a few steps from the Beach

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful, friendly Beach Condo” Beautiful Condo right on the beach with awesome sunsets from the roof and a Dunkin Donuts within walking distance. While the teen/young adult slept in, I visited DD and walked the beach. The owner had a manual that provided lots of activities around the area and places to eat. We enjoyed our stay and would definitely visit again!

Responds fast! avg. 1 hour 28 minutes

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Price per night from

$210

Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

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Price per night from

$193

Blue Bayou

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“"Home from Home"” A very well appointed apartment in a great location that had everything you would wish for to enhance your vacation experience. A real home from home that is clean, well furnished and spacious. The owners have been great to deal with and nothing is too much trouble. I have already recommended this accommodation to friends who were similarly impressed and we will be staying here for the third time later this year.

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Price per night from

$94

Luxury 3 Bedrooms/3 Full Baths, Private Heated Pool with Waterfall, Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Christmas at the Beach” It was a wonderful family vacation for two families going away for Christmas! There were 4 adults and 6 children! The pool was amazing and the house was perfect! Anna Maria Island is gorgeous and the house is in a perfect location for the beach, food and shopping! The owners were available for any needs that needed to be met! Awesome Owners!

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Price per night from

$234

Coconuts Beach Front 106 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$197

90 steps to the Beach!

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing” Absolutely loved our stay! Beautiful condo right next to the beach. Had everything we needed! We will definitely be back!

Match: Swimming pool

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Price per night from

$197

Holmes Beach Home w/Pool & Hot Tub, Walk to Beach!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

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Price per night from

$306

A Pearl of a Beach Home - with luxury private heated pool and hot tub

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“out standing place to stay” I would/will stay here again when we come back down. Everything is top notch and the home has everything you need. We enjoyed the pool and hot tube, used it every night. Mike and Lesley are very easy to work with and do anything to make things go smoothly.

Responds fast! avg. 1 hour 17 minutes

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Price per night from

$285

Coconuts Beach Front 107 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$315

Absolutely Perfect - Cove at Sandy Pointe #207

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$95

Coconuts Poolside Unit 104

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“The BEST spot on the island!” 24 hours ago we got home from our vacation to Anna Maria at the Coconuts! I'm already wishing we could get a plane and head back!! We absolutely love this island.. And finally lucked out finding the perfect place to stay! We rented a pool side room which was perfect for my family! My daughter couldn't wait to get up and jump in the pool at 9am and just a few steps walk out of the pool gate was the GULF! The location could not be better. The beach wasn't busy like around the public entrances we have previously been on. We could even cast out our poles and catch fish while we enjoyed the beach. My 8 year old daughter caught 5 fish right off the bat Saturday morning! The actual room was great too! Very old school Florida beach feeling to it.. It really felt like the island life! If your looking for a top of the line updated place.. This wouldn't be your place. But if your just looking for that true island feeling.. It's here! It has everything you could possibly need on a condo.. Other then a washer and dryer, but they are on site and I was able to come home with clean luggage to put away! The only complaint we have is the beds.. They were not comfortable at all. Doing our full 10 vacation on those would have been tough. The pricing was VERY reasonable also.. A lot of places on the island can get pricey. The Resort on all was awesome tho! We love it.. And we will be back next year

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$163

Coconuts Beach Front 109 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$200

Coconuts Two Bedroom Unit 117 Upstairs Courtyard

Holmes Beach villa

1 bedroom / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$201

Coconuts Beach Front 105 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$200

Coconuts Two Bedroom 118 Upstairs Courtyard

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$201

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 49 minutes

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Price per night from

$233

3A Villa's on Anna Maria Island

Holmes Beach villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 38 minutes

Match: Swimming pool

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Price per night from

$142

coconuts Courtyard 114 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 38 minutes

Match: Swimming pool

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Price per night from

$153

Coconuts Beach Front 112 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

Match: Swimming pool

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Price per night from

$201

$300 OFF MARCH PARADISIAC ENCLAVE 5* Waterfront Canal Pool Home-Dock/Kayak/BikeS

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 47 minutes

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Price per night from

$326

Coconuts Courtyard 119 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$193

Coconuts Beach Front 108 Ground floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Great” Great location! Beautiful view. The condo was was spacious enough for a small group. The beds were a little harder than I would like but the location of the condo and view were great.

Responds fast! avg. 3 hours 57 minutes

Match: Swimming pool

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Price per night from

$197

Coconuts Poolside Unit 102

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

Match: Swimming pool

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Price per night from

$163

Sandy Pointe 110, recently remodel, pet friendly

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$172

Coquina Sands, view beach from balcony, priv pool

Holmes Beach house

2 bedrooms / 3 bathrooms / sleeps 6

“Great place, great location, great vacation” We stay at Anna Maria for 12 days and if we could we would be there for 12 years. Awesome place and great host. Everything was ready for us. Only high marks. Thanks

Responds fast! avg. 3 hours 38 minutes

Match: Swimming pool

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Price per night from

$235

Ah this is it v2.0! Lemon Cottage w Pool!! Relax!!

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

“Way more than we expected!” Our week at Lemon Cottage was just excellent! Owner, Chris, has thought of everything we would need for the beach. The house is lovely inside, and landscaped just as nicely outside. We used the two bikes to explore, and we took many walks. The lanai area, with pool, is so inviting, that we managed to spend many hours out there just relaxing and trying to decide why we needed to move on to any activity at all! One of the things we did was to take a boat trip with Captain Kim (which I had done before). We stopped at the low places in the bay at low tide and held many live sea creatures...a great trip for adults as well as children. Mote acquarium is also high on my list, and they also have an educational boat tour of Sarasota Bay. Ringling mansion tour and grounds was lovely as well, even though we were caught in a deluge of rain. Lemon Cottage was indeed a lovely place to spend a week and we are hopeful that we will be able to stay there again. I highly recommend it!

Match: Swimming pool

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Price per night from

$207

Island Vacation Rental

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Island Paradise” The moment we arrived, exhausted after many delays and problems, the Thomas' home became our home. The condo is well appointed, with comfortable beds, a wonderful kitchen and a fully stocked linen closet, right down to beach towels. Laine, Kevin and Howard are so responsive and saw to all of our needs. Location was prime. We walked to get groceries, eat and do other shopping. There were 7 miles of beaches to explore and the quaint villages of anna Maria and Cortez and Bridge Street kept us occupied when we weren't soaking up the sun. The lanai was my favorite place to drink my coffee and check out the action at the pool each morning . We ate the majority of our meals there, under the twinkling lights. It was a wonderful month!

Match: Swimming pool

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Price per night from

$148

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Match: Swimming pool

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Price per night from

$217

3B Villas on Anna Maria Island Two Bedroom

Holmes Beach villa

2 bedrooms / 1 bathroom / sleeps 6

“Vacation” Nice quiet clean and had everything we needed we had a wonderful time and the beach is only a block away

Responds fast! avg. 3 hours 38 minutes

Match: Swimming pool

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Price per night from

$183

Coconuts Beach Front 110 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

Match: Swimming pool

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Price per night from

$201

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“A trip to paradise.” From the breathtaking views of both the Gulf and the Bay to the wonderful, eclectic furnishings, this condo is everything one could hope for. It has great amenities for entertaining friends and every convenience you will need. The heated pool overlooks the Gulf and allows direct access to the beach and the elevator provides ease in getting up to the condo. This vacation was the most enjoyable I've ever experienced.

Responds fast! avg. 3 hours 4 minutes

Match: Swimming pool

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Price per night from

$395

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Famous Holiday” Everything was so perfekt ... WE CAME back next Year THE HOUSE BEAUTIFUL AND CLEAN.. THE Area perfekt

Match: Swimming pool

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Price per night from

$264

Lifestyle on the island

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$95

Holmes Beach Family Home w/Private Pool & 3 Decks!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

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Price per night from

$238

1A Villas on Anna Maria Island One bedroom

Holmes Beach villa

1 bedroom / 1 bathroom / sleeps 4

“Cute cottage.” Close to the beach, unit 1a had everything we needed. It had a comfortable king bed, small kitchen and internet connection. It was a great choice for us!!! Great value for the price.

Responds fast! avg. 3 hours 38 minutes

Match: Swimming pool

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Price per night from

$142

Coconuts Courtyard 116 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

Match: Swimming pool

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Price per night from

$152

Contemporary Beach House, Very Private Yard & Pool - 1.5 Blocks to Beach

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 58 minutes

Match: Swimming pool

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Price per night from

$209

Viewing 38 of 1,769
rentals in Holmes Beach

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