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4,041 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 Linen 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 Linen 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, Linen provided

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Price per night from

$271

Gated Gorgeous Family Home Near Downtown Tampa & Beaches!

Riverview house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 3 minutes

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

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Price per night from

$402

SunWay Suites Unit 1 Sandpiper

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$149

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, Linen provided

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Price per night from

$205

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, Linen provided

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Price per night from

$126

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, Linen provided

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Price per night from

$459

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, Linen provided

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Price per night from

$259

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, Linen provided

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Price per night from

$197

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Linen 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, Linen 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 34 minutes

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

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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, Linen provided

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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, Linen 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, Linen provided

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Price per night from

$166

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, Linen provided

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Price per night from

$401

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, Linen provided

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Price per night from

$274

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, Linen provided

2 of 3 filters match

Price per night from

$400

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, Linen provided

2 of 3 filters match

Price per night from

$308

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, Linen provided

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Price per night from

$263

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, Linen provided

2 of 3 filters match

Price per night from

$308

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, Linen provided

2 of 3 filters match

Price per night from

$286

Gulfport Waterfront Mid-Century Modern Masterpiece

Gulfport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$367

♥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, Linen provided

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Price per night from

$213

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, Linen provided

2 of 3 filters match

Price per night from

$160

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, Linen provided

2 of 3 filters match

Price per night from

$460

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, Linen provided

2 of 3 filters match

Price per night from

$458

Lido Sunshine L

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

2 of 3 filters match

Price per night from

$171

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, Linen provided

2 of 3 filters match

Price per night from

$242

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, Linen provided

2 of 3 filters match

Price per night from

$230

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, Linen provided

2 of 3 filters match

Price per night from

$84

Sunshine Paradise at Redington Beach

Redington Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$229

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, Linen provided

2 of 3 filters match

Price per night from

$170

Downtown Largo Cottage

Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$218

Renovated Beachside Condo

Belleair Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$252

Amazing themed home at Solara Resort

Four Corners house

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 20

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

2 of 3 filters match

Price per night from

$321

Direct Beachfront Delight: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$240

Viewing 38 of 4,041
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