Holiday rentals in Longboat Key

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Top-rated holiday rentals in Longboat Key

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Guest favourite

Home in Longboat Key

4.87 out of 5 average rating, 106 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

14–21 Dec

$794 SGD per night

Guest favourite

Flat in Longboat Key

4.82 out of 5 average rating, 124 reviews

Ocean Front Studio Special From $99/night

This complex is a 2 story bldg with only 14 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures are taken from the condo, so what you see is what you get, direct beautiful Ocean views. Sip your beverage of choice as you enjoy the sunsets and the balmy breezes on your large walkout private patio with a table, chairs, chaise lounges which faces the aqua waters of the Gulf of Mexico. This is a condo that you will want to return to year after year.

13–20 Aug

$292 SGD per night

Guest favourite

Guest suite in Sarasota

4.97 out of 5 average rating, 293 reviews

Mid-Century Suite w/ Private Entrance

Cute master suite w/ private bathroom and private entrance through backyard (no access to main house- think "mother in law suite"). Private and no access to rest of home. Self check in w/ coded lock. Lanai has washer/dryer and seating area. Mini fridge (w/ small freezer), microwave and nespresso machine, water kettle. Filtered water provided. TV w/ Netflix. Wifi. Queen bed. Small desk. Private full bathroom w/ bidet. Also has outdoor sink and shower (cold only). Controllable a/c unit in room.

25 Jul – 1 Aug

$135 SGD per night

Guest favourite

Guest suite in Sarasota

4.98 out of 5 average rating, 106 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

5–12 Sep

$159 SGD per night

Guest favourite

Guest suite in Sarasota

4.98 out of 5 average rating, 194 reviews

The Sapphire Suite 1Bed/1Bath

Beautifully elegant suite with a relaxing touch. A pleasant mix of Hispanic and Modern decor in a newly renovated living area complete with all necessities such as wifi, an outdoor patio and your own free parking. The suite is located MINUTES away from all of Sarasota's famous hotspots! It is down the street from Jungle Gardens. A 10minute walk to The Ringling Museum. 10minute drive to Downtown, 15 minute drive to both Siesta Key and St. Armand's Circle. It could not be located more ideally!

3–10 Aug

$166 SGD per night

Guest favourite

Apartment in Longboat Key

4.86 out of 5 average rating, 155 reviews

The Beach Condo Unit #107 Beachfront

Unit #107 has a private beach access, This end condo unit is quiet, ground floor and only steps to the white sand beach down a private path. . Note that this is a small studio, 330 sq. ft. with queen murphy bed and a queen sofa bed. It has no separate bedroom. Full view of gulf and sunsets. There are only 15 units in the complex, few people on beach or at the heated pool. No daily maid service. Only initial limited supply of products/soaps/towels. Common use W/D across from unit.

25 Oct – 1 Nov

$436 SGD per night

Guest favourite

Apartment in Longboat Key

4.93 out of 5 average rating, 145 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

6–13 Nov

$424 SGD per night

Guest favourite

Apartment in Longboat Key

4.97 out of 5 average rating, 149 reviews

Charming Condo on the Coast!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with complimentary chairs and umbrellas. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

22–29 Nov

$436 SGD per night

Guest favourite

Guest suite in Bradenton

4.93 out of 5 average rating, 138 reviews

Live and Enjoy Arlet’s Dream

Enjoy the simplicity of this quiet and central accommodation from which you can easily access exquisite restaurants, fast food place, airports, shopping malls, cultural and recreational centers as well as the beautiful beaches that characterize this city .Feel the warmth and enjoy the great sunset of Ana Maria Island and Coquina beach.Walk along the white and fine sand of a set of beaches that will be within your reach due to the central and privileged location of this accommodation.

11–18 Jul

$139 SGD per night

Guest favourite

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Bella Vita! (The Good Life!)…that feeling when you wake up each day in this little slice of Paradise. This is the spot to enjoy a warm peaceful getaway from the rest of the world...just arrive with your bathing suit/flip flops and walk 1.5 blocks to the warm Gulf waters. Tranquillity of beach life, beautiful sunsets and lazy days of fishing and bird watching. Visit the Jetties, where you can see dolphins, manatees and rays, is only 1/2 mile away.

11–18 Aug

$165 SGD per night

Guest favourite

Home in Sarasota

5.0 out of 5 average rating, 279 reviews

Stunning Luxe Casita- Gateway to Siesta Beach

Newly built and completed in 2019; this guest house is just a few minutes walk to one of the world's best beaches, Siesta Key. Your own private drive to this elegant secluded enclave is close to shopping, restaurants and all the fun Sarasota and Siesta Key offer. Tall ceilings, double pane windows, extraordinary insulation, beautiful finishes and furnishing details make this an unusually quiet and comfortable refuge.

10–17 Oct

$304 SGD per night

Guest favourite

Apartment in Longboat Key

4.8 out of 5 average rating, 213 reviews

SRQ/Longboat Key Beach - kid friendly/romantic B1

Beachfront on beautiful Longboat Key, this condominium, unit 234, offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air.

29 Mar – 5 Apr

$269 SGD per night