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Holiday rentals with outdoor seating in Longboat Key

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Top-rated rentals with outdoor seating in Longboat Key

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Home in Longboat Key

4.86 out of 5 average rating, 110 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

Guest favourite

Apartment in Bradenton Beach

4.91 out of 5 average rating, 150 reviews

Post storm Re-Opening November 5 Anna Maria Island

Stop searching you found your beachfront vacation. No sitting in traffic for 90 minutes to get over the drawbridge to Anna Maria Island and looking to park for $20 an hour. You only have to go down 14 stairs from your second-floor condo to have your toes in the powder soft sand. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway or bring the kids for a fun stay at the beach. One of the best values on AMI as featured by trip101 article in pics 2&3

Guest favourite

Home in Bradenton Beach

4.97 out of 5 average rating, 159 reviews

Welcoming Back Guest: Jan 1, 2025!

Less than a 2 minute WALK from the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. With large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with a bathroom on opposite ends of the house (a pocket door adds privacy). Private heated salt water pool sits amidst the lush tropical yard. Hop on the free A/C'ed trolley and explore Florida's gorgeous Anna Maria Island.

Guest favourite

Guest suite in Sarasota

4.99 out of 5 average rating, 143 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!

Guest favourite

Apartment in Longboat Key

4.91 out of 5 average rating, 160 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.

Guest favourite

Apartment in Longboat Key

4.99 out of 5 average rating, 112 reviews

One-Bedroom Condo on the Coast!

This charming seaside condo 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 one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

Guest favourite

Guest suite in Sarasota

4.93 out of 5 average rating, 305 reviews

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *Private Studio* Access Non shared Pool. Studio w/private entrance & private patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/local markets/ dining/movies & shopping New King bed. New 50" TV. Off street parking. No Smoking/Vaping! Wet Bar, No kitchen, lite meals only! No hotels in my exclusive area! Live like a local!

Guest favourite

Guest suite in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 323 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. Controllable a/c unit in room.

Guest favourite

Guest house in Bradenton Beach

5 out of 5 average rating, 147 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Guest favourite

Guest suite in Bradenton

5 out of 5 average rating, 213 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Guest favourite

Guest house in Sarasota

4.98 out of 5 average rating, 253 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area offers. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

Guest favourite

Serviced apartment in Siesta Key

4.99 out of 5 average rating, 165 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

SIESTA KEY IS GETTING BACK TO NORMAL! WE ARE OPEN! Beautiful apartment in Siesta Key Beach. Fully equipped. Condo hotel, on the best area of the beach in Siesta. Main bedroom with King bed. 2nd room with two single beds. Queen sofa bed in the living room. Pack n Play & high chair for children. 1200 MB Wifi. 70” Smart TV, 2 55” TVs Nesspreso, Keurig.

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Popular amenities for outdoor seating rentals in Longboat Key

Free parking on premises

Air conditioning

House rentals with outdoor seating

Guest favourite

Home in Bradenton

4.94 out of 5 average rating, 247 reviews

Home near Anna Maria Beach w/ Hot Tub + Fire Pit

Guest favourite

Home in Plant City

4.99 out of 5 average rating, 481 reviews

The Strawberry Field Stilt House

Guest favourite

Home in Holmes Beach

4.97 out of 5 average rating, 128 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Guest favourite

Home in Bradenton

4.9 out of 5 average rating, 41 reviews

The "Love shack" Bungalow

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 37 reviews

Couple’s Seatreat Summer Rate Specials

Guest favourite

Home in Longboat Key

5 out of 5 average rating, 23 reviews

North Shore Six

Guest favourite

Home in Myakka City

4.98 out of 5 average rating, 145 reviews

Charming Country Stay (Near Lakewood Ranch)

Home in Holmes Beach

4.87 out of 5 average rating, 103 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

Apartment rentals with outdoor seating

Guest favourite

Rental unit in Sarasota

4.99 out of 5 average rating, 110 reviews

*Recently Updated* Cozy Oasis, centrally located

Guest favourite

Rental unit in Indian Beach-Sapphire Shores

4.97 out of 5 average rating, 112 reviews

Free Early Chk-in, Super Clean, New apt/bldg.

Guest favourite

Rental unit in Sarasota

4.87 out of 5 average rating, 141 reviews

Pets friendly modern studio 5 mi to Siesta Key

Guest favourite

Rental unit in Sarasota

4.98 out of 5 average rating, 165 reviews

Near Siesta Key Beaches - Quiet 1 BR apt

Guest favourite

Rental unit in Sarasota

4.88 out of 5 average rating, 147 reviews

Updated Old Florida Studio Getaway in Central SRQ

Guest favourite

Rental unit in Holmes Beach

4.96 out of 5 average rating, 155 reviews

Cabin 1 at Spinnakers Vacation Cottages

Guest favourite

Rental unit in Sarasota

4.91 out of 5 average rating, 266 reviews

The Tangerine Apart (Near Downtown/ Spacious)

Guest favourite

Rental unit in Venice

4.99 out of 5 average rating, 407 reviews

Hales Corner, Cozy & Private Beach Town Getaway

Apartment rentals with outdoor seating

Apartment in Siesta Key

4.82 out of 5 average rating, 205 reviews

No Damage: Cozy 1BR Beach Condo on Siesta Key!

Apartment in Lido Key

4.8 out of 5 average rating, 104 reviews

LIDO KEY 1 BR/1Bath Heated Pool 16

Guest favourite

Apartment in Indian Shores

4.99 out of 5 average rating, 108 reviews

Tropical Beachfront Penthouse-Beach Cottages II

Guest favourite

Apartment in Sarasota

4.85 out of 5 average rating, 137 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

Guest favourite

Apartment in Bradenton Beach

4.87 out of 5 average rating, 114 reviews

Charming and Updated 1 Bedroom in Runaway Bay

Guest favourite

Apartment in Holmes Beach

4.99 out of 5 average rating, 131 reviews

Beach Escape - Make Memories on Anna Maria Island!

Guest favourite

Apartment in Lido Key

4.96 out of 5 average rating, 132 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

Guest favourite

Apartment in Indian Rocks Beach

4.97 out of 5 average rating, 101 reviews

Private Ocean View Beach Retreat with Balcony

Quick stats about holiday rentals with outdoor seating in Longboat Key

Total rentals
340 properties
Nightly prices starting at
₹3,390 before taxes and fees
Total number of reviews
6T reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
270 properties have a pool

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