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5,254 guest houses

Close to Siesta key with hot tub, fire pit and butterfly garden

Gulf Gate Estates guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Towels provided Beach or lakeside relaxation

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Price per night from

$193

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Towels provided Beach or lakeside relaxation

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Price per night from

$172

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Christmas and New Year's Eve in Orlando, FL, 2- 8 people, 12/25-1/1

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$270

Renovated 1BR Haven - 2 Mins from Sunset Beach!

Treasure Island house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$205

Cute 1 bedroom - 5 min Walk to Beach

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$241

Starfish Bungalow 1B/1B 2 Min from Bay and Beach!

St. Pete Beach bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$458

SunWay Suites Unit 1 Sandpiper

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$149

Sarasota 2BR 2BTH Condo Close to Siesta Key Beach

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$60

The Sand Dollar: Historic Charm Meets Beach Chic in the Waterfront District

Gulfport apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$126

Ohana North 2 Bedroom

Holmes Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Outstanding” Rented the duplex for Father's day weekend and had a blast. Even though you are not directly on the water you can walk there in five minutes, or drive if you care to. Three blocks to the beach. The unit was exceptionally clean, beautifully decorated, and well stocked. Definately one the better units we have stayed in over the years. Brenda and Danny were a pleasure to work with and very accomadating. You will not be dissapointed staying here I assure you.

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$246

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$309

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 22 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$196

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$172

A Place In the Sun

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$172

2 bedroom condo, Coquina Key, Tampa Bay, Florida

St. Petersburg apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Waterside at Coquina Key has it all!” Waterside at Coquina Key is a a well kept up gated community that offers all the amenities a wonderful vacation requires. Marlean's condo provides a nicely updated unit that allows you to enjoy the waterside condos in comfort and provides all the extra's you need to relax and unwind in the peace and tranquility of a watersdie property. The kitchen had all you needed and more and was nicely updated and contained all you need to cook in or prepare a quick breakfast and take off for the pool or to work-out. The only small downside is not to have a wash and dryer available in the unit. Although one is available 24/7 as the clubhouse and you can use your debit card to work them. the beds were comfortable, and the living area had ample seating available. Thank your for shring your condo, it was wonderful.

Responds fast! avg. 1 hour 30 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$143

Oceanfront Condo at Beach Cottage One. 1400 SQ Ft with 2 King Beds.

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 51 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$212

Elegant Beach Front Penthouse on Desirable Belleair Beach, FL 2B/2B

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$201

Anna Maria 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!

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$166

3 bedroom, 2 bath home, just steps to the beach

Treasure Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“What a great week we had” We recently had a family reunion at this beach house. There were eight of us and there was plenty of room. The house was a wonderful place and we really enjoyed morning coffee around the island in the kitchen and s'mores in the evening on the back deck around the fire pit. Several times we grabbed a glass of wine and walked to the beach to watch the sunset and even saw a few dolphins. The area seemed to have a lot of events happening nearby, sand sculptures on the beach, shopping at a restored fishing village with several unique shops, bands on the sands and fireworks. The oversized wrap around deck added extra room to what already felt like a spacious house. The house is beautiful and we look forward to vacationing there again.

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$458

Once Upon a Tide: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$399

Casa Mar - Unit 58: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$308

Casa Mar - Unit 20: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$308

Spectacular sunsets await!

Indian Rocks Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$172

Casa Mar - Unit 22: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$262

Casa Mar - Unit 8: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$274

Tropical Retreat - Townhome Condo w/Patio - communal Pool - 3 min walk to Beach!

Indian Shores townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$401

Palm Cottage:Vintage Tropical Hideaway in the Waterfront District

Gulfport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Palm Cottage” Exceeded our expectations! Absolutely the perfect location. Palm Cottage was adorable, clean, well stocked with supplies, and sooo relaxing. Restaurants and beach an easy walk on brick streets. So much charm. Will definitely be back.

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$159

Bianco Sands 2 Bedroom - 2 Bath; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$297

♥EEV♥ Private Pool with Lake View - Couples Getaway

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$213

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 48 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$458

Steps to the Beach! Your Beach Getaway Awaits! Your Search Is Over!!

Indian Shores condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$458

Beautiful Beachfront Condo on the FL Gulf Coast

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful family beach vacation condo” The condominium is a great place to stay. All the amenities you need to enjoy a relaxing family vacation. There is an picturesque view of the beach on the balcony and a large pool to enjoy. The location of the condo is convenient to shopping and restaurants. Carol (the owner) is always very helpful and accessible if you have any questions about your stay. We have found a new place to stay on our summer vacation and can't wait to visit again next year!

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$241

MODERN CONDO IN GATED COMMUNITY MINUTE FROM BEACH

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Great condo” The condo was clean and very well appointed. Edith was reachable and a good communicator. Convenient location to Publix, restaurants, etc. The pool was nice, and gym was basic but usable. I would give the unit itself a 5 rating. However, there were two disappointments with the facility, neither of which has to do with the unit, but impacted our use. Although the pool says they are open dawn to dusk, the gates are locked with chains and padlocks until someone gets there to open it, so swimming and using the gym early in the morning was not an option. Frustrating if you prefer an early workout.

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$126

Sunset Beach One Bedroom Gulf View

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$229

Sunshine Paradise at Redington Beach

Redington Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$229

Lido Sunshine L

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$171

Fully renovated Apartment, Minutes 2 Beach, DownTown and Pinnellas Trail

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$170

Prime Location: Relaxing Stay near Beaches

Safety Harbor condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Beach or lakeside relaxation, Towels provided

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Price per night from

$84

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