
House vacation rentals in Longboat Key
Find and book unique houses on Airbnb
Top-rated house rentals in Longboat Key
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

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

Summer House longboat key
Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical 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. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Longboat Key Beach House
This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida getaway and includes your beach supplies. It’s only one block to the beach access, convenience store, great restaurants and a deli. Also Included is the use of a membership to Cedars East Tennis Club (5 minute walk), which has Pickleball and Tennis Courts, a junior Olympic POOL, gym, free bicycle rental and tiki bar. Minutes to Holmes, Bradenton and Coquina Beaches.

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Salty Harbor AMI pool retreat near the Beach
Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

Pool, Shuffleboard, EV charg, Near beach, UTC mall
Welcome to Vistalodgings Vista Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

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. VR24-00265

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!
Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. 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 bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Short walk to beach + Boat dock
The best of island living: a boat dock in back & deeded private access to the white sandy beaches of LBK, just steps down the street. Minutes from Coquina Beach, historic Bridge St. and Anna Maria Island. Sarasota, Lido Beach & St. Armands Circle are a short drive south. A well-stocked convenience store, deli and 3 restaurants (Continental, Italian and Mexican) are a block away; with Euphemia Hay, Lazy Lobster, Dry Dock, Chart House just a short drive.

"Little Siesta" - Farm home near Terra Nova
Unique, remodeled 1937 house that was moved from Siesta Key to the 1,100 acre Triangle Ranch. It sits directly on the Myakka River and has views of the river from the balcony or the back porch. "The Siesta" is a full size 1400 sq. ft. 2 story house with 2 bedrooms, 2 full baths, kitchen and screened-in porch. Shared firepit and picnic area.

The BEACH Life!
Newly remodeled 4 bed/3 full bath - 2200 sq ft. house! 150 yards WALK to the beach. Pool table! Plenty of off-street parking. A cafe and a deli, 3 pub/restaurants, a pizzeria and a local beach shop all 200 yards away. Tennis/Pickleball/Pool Private Club membership included - only a 5 minute stroll from the house.
Popular amenities for Longboat Key house rentals
House rentals with a pool

Ocean72 | Heated Pool & Spa | 2BR Near Beach

New! Heated Pool~Steps to the Beach/Shops~Starfish

Bayfront Beach access with Heated Pool!

The Peachy Beach House, steps to the gulf

AMI Cortez Beach Retreat "Views" Resort-style Pool

Luxe Oasis In St. Armands Circle with Private Pool

Waterfront Pool Home Steps to Beach

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach
Weekly house rentals

Waterfront Retreat in Apollo Beach– Relax & Unwind

Heated Pool, Hot Tub, Game Room, Steps to Beach!

83rd St Villas East by Duncan Real Estate

TOES IN THE SAND!

Luxury Canal-Front Home + Heated Pool Near Beach

Ocean Air Oasis-New Centrally Located AMI Luxury

Private Heated Pool Retreat for Two Families

Ocean Views - Spacious Unit, Bonus Loft & Hot Tub
Private house rentals

Rate Sale8/15 Pool~StepsToBeach BeachEquip~Grill

Beach Retreat! Paddleboards, Bikes, & Beach Gear!

AMI*Steps to the beach-Modern LUX* POOL SPA*Views

New! Heated Pool • Shopping • Pine Ave • Beaches!

Hidden Gem, Pool, Steps to Beach and St Armands

Walk to Beach + Trolley + Heated Pool + Mini Golf!

Stylish Pool Home • Near IMG & Beaches • Top Rated

“Topside” luxury home in Cortez Village
When is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,021 | ﺩ.ﺇ 1,050 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 936 | ﺩ.ﺇ 918 | ﺩ.ﺇ 808 | ﺩ.ﺇ 757 | ﺩ.ﺇ 749 | ﺩ.ﺇ 720 | ﺩ.ﺇ 701 | ﺩ.ﺇ 826 | ﺩ.ﺇ 944 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about house rentals in Longboat Key

Total vacation rentals
Explore 250 vacation rentals in Longboat Key

Nightly prices starting at
Longboat Key vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

Verified guest reviews
Over 4,720 verified reviews to help you choose

Family-friendly vacation rentals
220 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 120 rentals that welcome pets

Vacation rentals with a pool
160 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wi-Fi availability
250 of Longboat Key vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Longboat Key rentals

4.9 Average rating
Longboat Key stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Miami Vacation rentals
- Orlando Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Miami Beach Vacation rentals
- Panama City Beach Vacation rentals
- Tampa Vacation rentals
- Fort Lauderdale Vacation rentals
- Hollywood Vacation rentals
- Jacksonville Vacation rentals
- St. Augustine Vacation rentals
- Key West Vacation rentals
- Townhouse rentals Longboat Key
- Fitness-friendly rentals Longboat Key
- Rentals with outdoor seating Longboat Key
- Rentals with an EV charger Longboat Key
- Rentals with lake access Longboat Key
- Rentals with an accessible height toilet Longboat Key
- Pet-friendly rentals Longboat Key
- Rentals with pools Longboat Key
- Cottage rentals Longboat Key
- Rentals with a fire pit Longboat Key
- Rentals with a patio Longboat Key
- Waterfront rentals Longboat Key
- Beachfront rentals Longboat Key
- Family-friendly rentals Longboat Key
- Apartment rentals Longboat Key
- Rentals with beach access Longboat Key
- Rentals with a hot tub Longboat Key
- Rentals with a kayak Longboat Key
- Villa rentals Longboat Key
- Beach condo rentals Longboat Key
- Condo rentals Longboat Key
- Beach house rentals Longboat Key
- Rentals with a fireplace Longboat Key
- Rentals with a washer and dryer Longboat Key
- House rentals Manatee County
- House rentals Florida
- House rentals United States
- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Anna Maria Island Beach
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Amalie Arena
- Caspersen Beach
- Dunedin Beach
- Vinoy Park
- Tampa Convention Center
- Manasota Key Beach
- University of South Florida
- Hard Rock Casino
- Crescent Beach
- John's Pass
- Fort De Soto Park
- Tropicana Field
- Englewood Beach
- Sand Key Beach
- Anna Maria Public Beach





