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1,315 guest houses

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Shared outdoor pool (heated) 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, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$271

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, Shared outdoor pool (heated)

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Price per night from

$61

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, Shared outdoor pool (heated)

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Price per night from

$259

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

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, Shared outdoor pool (heated)

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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 34 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

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Price per night from

$144

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. 2 hours 11 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

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Price per night from

$213

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, Shared outdoor pool (heated)

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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, Shared outdoor pool (heated)

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Price per night from

$167

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, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$402

Casa Mar - Unit 58: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$309

Casa Mar - Unit 20: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$309

Casa Mar - Unit 8: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$274

Casa Mar - Unit 22: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$263

Once Upon a Tide: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$400

Bianco Sands 2 Bedroom - 2 Bath; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$286

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 41 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$460

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, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$127

Paradise Lane- Dolphin View on the Intercoastal Water !! Boats Welcome

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$483

Beachside Getaway Super Location

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$132

Luxury condo for ultimate Florida beach getaway

Treasure Island apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$258

Luxury Penthouse Condo Overlooking Beach/Gulf

Treasure Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Review” The place was amazing! Perfect weather and a great week! Thank you so much for the opportunity! We had the best week!

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$286

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great View” We stayed at Kathy’s condo during the 4th of July week. The Condo was great and the view was amazing. We enjoyed the fireworks display and easy access to the beach. We look forward to renting her condo again in the future.

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$315

Luxury 3BR GulfFront "Grateful to be at the Gulf"

Hudson apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 59 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$99

#6 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$345

#11 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$459

Four Shores # 2 “Beach” Condo is a 3 Bedroom/2 Bathroom Luxury Rental

Indian Shores condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$499

Four Shores Gulf Condo # 3 Direct Gulf w/ Pool & Spa

Indian Shores condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$499

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$278

Sunsets, Cocktails and Memories!

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Spacious and beautiful” My girlfriends and I just finished our stay for the third year in a row. This is an outstanding condo. With four or five of us, there is plenty of room. The private spiral staircase to the beach is great! No waiting for the elevator with everyone else. We love sitting on the porch early in the morning and again at sunset. Spectacular views! Also you can visit the Suncoast Seabird Sanctuary which is about 1/2 block to the south. Would highly recommend this condo. We hope to be back again next year.

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$382

Amazing 2BR Townhome, 2 min walk to beach! Spacious Patio, a Tropical Paradise!

Indian Shores condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$373

Luxury water views condo in a resort style complex with lots of amenities

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Excellent Holiday Getaway!” My husband and I stayed at this beautiful condo for a week in October 2013 and it was absolutely beautiful. It was exactly what we were looking for. Beautiful birds to see right at your door step. This luxury condo is very close to downtown which was good for night life and great food. I would recommend this condo to anyone. Also the owner Sabina was very welcoming which made us feel as if we were right at home!

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$201

Panoramic Ocean Views 2

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great place to stay” I stayed in this condo last February. It is calm, bright and perfectly clean. The balcony and the view on the water are outstanding! In addition to that, Sabina is perfectly organized, answered all the question I had and made sure I was feeling perfect. I definitely recommand it!

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$201

Bianco Sands - 2 Bedroom - Poolside: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$332

Coral Reef Beach Resort

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$328

Bianco Sands - 1 Bedroom 1 Bath: By Beachside Management

Siesta Key villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$228

Bianco Sands - 3 Bedroom 2 Bath: By Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$308

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