Family-friendly holiday rentals in Longboat Key

A spacious sleeping area features a plush king bed with silky white linens and decorative blue accents. A blue ottoman sits at the foot of the bed, while a large TV is placed on a dark wood dresser. Natural light filters in through the nearby balcony doors.

4.94 out of 5 average rating, 32 reviews

Waterfront Coastal Retreat | Steps from LBK Beach

Welcome to paradise— your tropical escape awaits! Wake up to island serenity in our brand NEW STUDIO SUITE where you'll enjoy peaceful lagoon views from your private balcony. This gem, located in the coveted Longboat Key Resort Club, beautifully blends modern touches with coastal charm. Bask under the sun and enjoy private access to Longboat Key Beach and the heated resort pool which is just steps away. Perfectly positioned for relaxation, adventure, and exploring the best of Downtown Sarasota.

KitchenFamilyLaundry

4.96 out of 5 average rating, 210 reviews

A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.

Home in Bradenton beach

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

KitchenIndoor spacesCleanliness

4.97 out of 5 average rating, 112 reviews

The exterior of the beach house is depicted, showcasing a blue structure with a metal roof surrounded by tropical landscaping. A gravel driveway leads to the entrance, flanked by palm trees and vibrant foliage, emphasizing the inviting coastal atmosphere.

Home in Longboat Key

Beautiful Beach House

Beautiful, updated 1937 beach house. Original LongBeach cottage. Gated entrance to property. Three bedroom, two bath. Master bathroom has bathroom en suite. Hardwood floors throughout. Kitchen updated. Beautiful front and back porches to enjoy the sunshine. Private access to beach and Gulf of Mexico. Walking distance to shops and Tennis. Bedrooms include master with King, second bedroom with queen, third bedroom with two twins. Come join us in longboat key for sunshine, beaches,culture,tennis

FamilyIndoor spacesQuiet

4.95 out of 5 average rating, 197 reviews

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

KitchenFamilyCondition

A sandy pathway leading to a beach is framed by lush dune vegetation. The scene captures a vibrant sunset over calm waters, with soft clouds reflecting warm hues. Natural light creates an inviting atmosphere, highlighting the serene transition from land to sea.

4.8 out of 5 average rating, 143 reviews

Gulfront Views! BEACHFRONT BARGAIN HUNT NOMINATED

THIS UNIT WAS NOMINATED TO BE FEATURED ON BEACHFRONT BARGAIN HUNT! Unit #102 Features: Full-size kitchen and Gulf-front views Bedding: 1 Queen Murphy Bed and a Sleeper Sofa Savor warm Gulf breezes while resting lavishly in this Gulf-front condo complex. Located directly on the beach, this resort features beautiful Gulf-front views. You are only steps from the white-sand beaches, placid turquoise waters and beautiful sunsets that will have you daydreaming about your next beach vacation.

Indoor spacesKitchenLong stay

The image captures a serene beach scene, showcasing gentle waves lapping at the shore under a bright blue sky. Tall grasses sway gracefully in the foreground, while lush greenery borders the sandy beach, leading to the calm, turquoise waters of the Gulf.

5.0 out of 5 average rating, 118 reviews

Beach Bliss: Open Sun & Mon $199/nt + Fees!

This sublime oceanfront studio condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the ground floor, overlooking the heated pool and ocean, this dreamy studio is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

KitchenFamilyView

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

4.9 out of 5 average rating, 235 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 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.

FamilyIndoor spacesBarbecue

4.9 out of 5 average rating, 20 reviews

Home in Longboat Key

Dog friendly LBK home with deeded access to beach!

**Calendar not always up to date. Please message me for specific dates. Newly renovated 3/2. Location, location, location. Walk or ride bikes to some of the top restaurants on LBK. Perfect for a small family or two couples. Beautiful outdoor screened in porch with grill, couches, dining room set and and ping ping table, outdoor living at its best. Tenants also get to enjoy Cedar’s Racquet Club membership with pool, tennis, pickle ball, full gym and bikes.

FamilyKitchenCondition

An aerial view shows a two-story beachfront property with direct access to the beach. A shared pool is visible in the center, surrounded by lounge chairs. The studio unit is indicated with a blue circle on the left, featuring a patio area and proximity to the sandy beach.

4.87 out of 5 average rating, 209 reviews

The Beach Condo #107 Beachfront Full View

Unit #107 has private beach access. Only a few steps to the beach will full gulf view. This end condo unit is quiet, ground floor . It is a small studio: new queen murphy bed and queen sofa bed. No separate bedroom. Limited initial limited supply of products/soaps/towels. Common use W/D across from unit. This is a small studio at 330 sq ft. It has been recently remodeled. Grounds, unit, pool recently renovated due to hurricanes.

KitchenIndoor spacesTV

4.97 out of 5 average rating, 64 reviews

Beach Condo with Quiet, Private Beach

Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat.

KitchenIndoor spacesOutdoor spaces

4.9 out of 5 average rating, 124 reviews

Beachfront Escape – Private Balcony, Gulf Views

Beachfront Condo – No Street to Cross, Just Steps to the Sand Enjoy panoramic Gulf and sunset views from your private covered balcony in this spacious 1-bedroom, 1-bath condo on the 4th floor of Turtle Crawl Inn. Located directly on the beach in beautiful Longboat Key, FL, this unit offers unobstructed 180° views from every room and the peaceful sound of the waves just outside your door.

Indoor spacesFamilyLaundry

4.98 out of 5 average rating, 126 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

KitchenIndoor spacesCondition

Popular amenities for Longboat Key family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.

4.96 out of 5 average rating, 124 reviews

Longboat Key-OCEAN FRONT- on the beach

Indoor spacesKitchenBarbecue

4.93 out of 5 average rating, 137 reviews

A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.

Home in Tampa

The Jungalow SOHO - Pool/Hot Tub

KitchenFamilyQuiet

4.82 out of 5 average rating, 103 reviews

An outdoor dining area is set with a glass table and six blue chairs, shaded by a blue umbrella. In the background, a swimming pool with surrounding tropical plants invites relaxation, while a spa is visible nearby, offering a serene ambiance.

Home in Holmes Beach

Private pool, only two blocks .3 miles from beach!

Indoor spacesFamilyBarbecue

4.96 out of 5 average rating, 126 reviews

Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.

Home in Bradenton Beach

Waterfront Pool Home Steps to Beach

FamilyKitchenBackyard

5.0 out of 5 average rating, 115 reviews

Home in Arlington Park

The Blessing House- Htd Pool/Spa, Close to Beaches

FamilyIndoor spacesBeach

4.99 out of 5 average rating, 101 reviews

A well-maintained front yard features lush green grass and a large agave plant. The house, showcasing a contemporary design, is flanked by palm trees. A driveway leads to a two-car garage, with additional landscaped areas adding to the outdoor appeal.

Home in Cortez

Dockside Dreams - Pool, Spa & Waterfront Dock

FamilyKitchenNearby

4.96 out of 5 average rating, 111 reviews

Sun-filled cottage with pool, walk to beach

Indoor spacesKitchenAccuracy

Apartment in Bradenton Beach

4.86 out of 5 average rating, 436 reviews

Las Palmas Beach Rentals unit 2

FamilyIndoor spacesCleanliness

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 425 reviews

A serene outdoor space features a sparkling pool surrounded by lush greenery and tropical plants. Comfortable lounge chairs are placed along the poolside, and string lights cast a warm glow overhead. A shaded seating area with a gazebo can be seen in the background.

Home in Bradenton

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

Indoor spacesKitchenGetting around

4.81 out of 5 average rating, 115 reviews

Home in Bradenton Beach

AMI Sunset Beach - Gulf View Retreat w/ Pool+Decks

Indoor spacesFamilyWalkability

4.85 out of 5 average rating, 117 reviews

LUXE! Heated Salt POOL! Close to Town, Beach, IMG

FamilyIndoor spacesParking

4.98 out of 5 average rating, 202 reviews

A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.

Home in Bradenton Beach

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

FamilyIndoor spacesCheck-in

4.95 out of 5 average rating, 124 reviews

A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.

Home in Holmes Beach

Breezy Harbor AMI pool retreat near the Beach

Indoor spacesKitchenParking

4.94 out of 5 average rating, 100 reviews

A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.

Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

KitchenFamilyAccuracy

5.0 out of 5 average rating, 31 reviews

Home in Saint Armands

Luxury Lido Key Heated Pool & Game Room

FamilyIndoor spacesValue

5.0 out of 5 average rating, 6 reviews

Cottage in Longboat Key

Longboat Key Seaside Retreat

Indoor spacesFamilyBathroom

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 27 reviews

Just renovated, beach view from balcony Unit 203

KitchenFamilyBeach

5.0 out of 5 average rating, 30 reviews

Cozy private beach condo

KitchenFamilyAccess

A screened balcony provides an unobstructed view of the Gulf of Mexico, showcasing vibrant turquoise waters and a sandy beach. Lush greenery borders the foreground, enhancing the serene coastal landscape under a clear blue sky.

4.85 out of 5 average rating, 47 reviews

3 BR Condo On Longboat Key Beach and Waterfront

KitchenFamilyHiking

4.95 out of 5 average rating, 21 reviews

Home in Lido Key

Beautiful Home Steps to Gulf w/ Pool, Spa & Views

KitchenFamilyCondition

Aerial view of a wide beach features soft white sand and gentle waves lapping at the shore. The water displays a gradient of turquoise to deep blue, with scattered footprints in the sand. The horizon meets a clear sky, enhancing the open coastal atmosphere.

4.94 out of 5 average rating, 67 reviews

Turtle walk - Next to 7 top eats-Beach Easy walk

FamilyKitchenHospitality

4.83 out of 5 average rating, 6 reviews

Gr8 Vibes by Duncan Real Estate

KitchenIndoor spacesHospitality

5.0 out of 5 average rating, 6 reviews

Second Floor Studio- Amazing Gulf Front Views

LocationHospitalityAccuracy