Houses Longboat Key

Updating...

age 0-16
897 Results

Relevance

Price: low to high

Price: high to low

Reviews

897 houses

Bermuda Bay Club Un09 Special discount for February price reduced last minute

Bradenton Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Excellent accomodation and locality” This is the second time we have stayed here, in different units. Everything was excellent. No fuss, and just so convenient with the trolley at the roadside and the beach a walk across the road

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$344

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

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$345

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$287

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$278

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$286

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$173

Off the Hook: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$516

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$402

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$683

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$173

Siesta Dunes #300: By Beachside Management

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$332

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$46

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Clothes dryer Shared outdoor pool (heated)

All filters match

Price per night from

$173

These homes match some but not all of your filters. Clear all filters

4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Clothes dryer, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$339

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 3 match: Clothes dryer, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$2,984

Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Clothes dryer, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$394

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

2 of 3 match: Clothes dryer, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$517

St Armand's Private Home on Jackson Drive

Lido Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Clothes dryer, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$383

Limefish

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Clothes dryer, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$2,066

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

2 of 3 match: Clothes dryer, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$1,148

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$402

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$345

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, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$310

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$173

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$259

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$166

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, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$315

Crystal Sands Unit 308 Siesta Key, Florida

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$431

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$101

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$107

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$190

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$431

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$144

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$161

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$338

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$209

Newly remodeled condo on the Bradenton Riverwalk

Bradenton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$109

Sea~N~Blue

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Clothes dryer, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$402

Viewing 38 of 897
rentals in Longboat Key

×

Also consider