Family-friendly holiday rentals in Whitney Beach

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

#terraceLIFE | 2 Blocks to Beach | Heated Pool

Escape to our cozy beachside retreat, steps from the sand! Retire the car in the garage, fill the wagon w/beach supplies & head to the shoreline at sunset. Spend time sipping coffee on 1 of the 3 balconies or cooling off in the pool w/the lush landscape. There's no better way to relax & enjoy AMI! Bedrooms on 2nd floor giving the main level separation. Sleeps 4-5 comfortably but can accommodate 6 w/sofa bed. Forgot something? Walgreens is right next door along with restaurants, shops & more!

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

Cozy private beach condo

Relax with the whole family at this peaceful place to stay steps away from the legendary longboat key private beach! Enjoy breakfast, lunch or dinner with the beautiful view of the Golf of Mexico right from your lanai. This lovely condo has 2 bedrooms 2 bath with small office and full equipped kitchen. The condo is located in a second floor accessible by stair and just a short walk to the complex 600 feet of white sand beach front, heated pool and bbq area. Minimum of 2 week rental available

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

Gulfcoast Getaway!

This charming seaside condo is on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! 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 secluded beach. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort! To see all four of our listings, click on my Host photo and scroll down...!

Waterfront 2BR 2BA | Pool - 10 min walk to Beach

A spacious first-floor 2-bedroom, 2-bathroom condo with direct pool access and stunning bayfront views. Located just a 10-minute walk to the beach, this beautifully appointed retreat offers the perfect blend of comfort, relaxation, and convenience. Enjoy a private patio overlooking the bay, a fully equipped kitchen, and a bright, open living space. With resort-style amenities, including a pool, hot tub, and tennis courts, it’s an ideal escape for couples, families, and remote workers.

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.

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.

New Modern on Beach- Walk out 5 steps to Sand

Newly renovated modern first floor condo literally five steps away from the sand walking outside from the lanai. One bedroom /One bath King bed in Primary Queen sleeper sofa in living room Key code entrance Free parking Heated Swimming pool on site Free Beach loungers on the beach Paid laundry machines on site Mid Island next to everything WiFi, cable, free parking Usually 7 night minimum Bring your toothbrush and bathing suite and prepare to unwind and relax!!!!

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. A guest-loved home, consistently rated top 5% among Airbnb’s homes.

Bradenton Beach Sunsets 2, 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.