Guesthouse vacation rentals in Dunedin

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Top-rated guesthouse rentals in Dunedin

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Clearwater

4.92 out of 5 average rating, 332 reviews

Clearwater Guesthouse w/ King Bed, Near Beaches

This private home away from home sits behind the main house in a quiet neighborhood conveniently located near downtown Clearwater, Clearwater Beach, Tampa, St Petersburg, Dunedin, Tarpon Springs, and other great towns. Located near Beaches, restaurants, shopping, & entertainment venues. • Clearwater Beach= 4 miles / 8 minutes • Downtown Dunedin= 3 miles • Honeymoon Island= 9 miles • Tarpon Springs Sponge docks= 14 miles • Tampa Airport (TPA)= 14 miles • St Pete/Clearwater Airport (PIE)= 9 miles

Jun 6 – 13

ﺩ.ﺇ303 per night

Guest favorite

Guesthouse in Gulfport

4.92 out of 5 average rating, 729 reviews

graceful haven...

This boutique-sized, moon-drenched studio is more than just a place to lay your head. From the delicate metal birds swirling above your bed, to the tender light reflecting off the burnished aluminum countertop, your senses will be soothed and tickled by its quietly exuberant design & decor. Nestled in a lush tropical garden, the space is just a block away from Gulfport's Art Village with its sunset waterfront, delightful shops, and many fine restaurants. (or, see my “bohemian treat” listing)

Jan 13 – 20

ﺩ.ﺇ426 per night

Guest favorite

Guesthouse in Largo

4.99 out of 5 average rating, 301 reviews

Paradise Cottage Largo 2 miles to beach private+

We are PARADISE COTTAGE and the standards of super host are status quo! Come on down - we're ready for you! Although only 2 miles from the Gulf, we're on high ground! We are on a Priority One Energy Grid. With over 300 plants, many trees, we live in a lush tropical "Paradise". Our guests' highest praises include the private, quiet, serene, safe and secluded attributes we're fortunate to claim, no neighbors while being so close to so much. Read on in the next section "The Space" to learn more

Nov 20 – 27

ﺩ.ﺇ525 per night

Guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 201 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to Patio, Swimming Pool , Backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Apr 11 – 18

ﺩ.ﺇ440 per night

Guest favorite

Guesthouse in Seminole

4.95 out of 5 average rating, 146 reviews

Quiet & Cozy Guesthouse minutes to the beach.

Newly remodeled, quiet and cozy guest house on a cul de sac. Great location close to shopping/restaurants, 4 miles to Gulf Blvd where you will find many beautiful beaches. 4 Miles to Madeira Beach/Treasure Island, 9 miles to Clearwater and St Pete Beach. 1 Bedroom, queen bed, and sofa bed in living room which pulls out to a queen bed. Full kitchen with all the extras. Cable TV, WiFi, 1 private parking spot and access to washer/dryer for stays 4 nights or more. No pets, no children under 12.

Nov 29 – Dec 6

ﺩ.ﺇ325 per night

Guest favorite

Guesthouse in Clearwater

4.93 out of 5 average rating, 369 reviews

Magical Garden Paradise: Hunt Haven Hideaway.

In the heart of Clearwater, a peaceful artists' retreat that will remind you of TN or North Carolina. If you like nature, this is the spot for you! Wander through the "Florida natural" garden and find spots for relaxation or conversation. If you like baseball, we are close to two SPRING TRAINING stadiums and 25 minutes from Raymond James Stadium. About 20 minutes from the beach, if you prefer fun in the sun. Safe, clean gated property centrally located for shopping and activities.

Dec 11 – 18

ﺩ.ﺇ499 per night

Guest favorite

Guesthouse in St. Petersburg

4.98 out of 5 average rating, 132 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. DEI honored here. Come & enjoy!

Oct 15 – 22

ﺩ.ﺇ473 per night

Guest favorite

Guesthouse in Clearwater

4.96 out of 5 average rating, 117 reviews

Studio Bedroom - Private Bathroom , Full Kitchen.

Enjoy your stay in Clearwater, Florida at this cozy, newly remodeled studio! The sanctuary is a place for you to retreat, relax, reset and revive yourself. It is a mini-retreat especially designed for you to come alone, or with a friend or partner. This studio is centrally located near downtown, and a a short drive from the beaches. Don't want to go out? There is everything you need - access to a full patio, jacuzzi, bar, and outdoor dining area is also available during your stay!

Feb 2 – 9

ﺩ.ﺇ724 per night

Superhost

Guesthouse in Tarpon Springs

4.84 out of 5 average rating, 287 reviews

Papa Bear's Cottage Two Bedroom Vacation Rental

A simple, yet magical second-story guesthouse, nestled into a yard of Spanish Moss and Magnolia trees, above a garage (no one will be in the guest house but you!). Minutes from downtown Tarpon Springs and the famous Sponge Docks, and 15 minutes from beautiful Gulf beaches, 30 minutes from Clearwater Beach. Hunkered in at the end of a private drive, on over two acres of quiet, enchanting land. You and your crew will enjoy the respite, nature, and coziness of Papa Bear's Cottage!

May 27 – Jun 1

ﺩ.ﺇ427 per night

Guest favorite

Guesthouse in Dunedin

4.94 out of 5 average rating, 135 reviews

Tiki Hut Cottage

Watch this video first to experience the property https://vimeo.com/444390022 This unit is privately located on the property, plenty of space for 4 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom with office space has a walk in shower with stack washer and dryer. Spacious living area with a fully functional kitchen. The property is an acre of lush tropical plants Conveniently located to the downtown & beach We allow a dog 35 lbs or less

Dec 14 – 21

ﺩ.ﺇ794 per night

Guest favorite

Guesthouse in Clearwater

4.9 out of 5 average rating, 182 reviews

Cottage on Pinellas Bike Trail

This cottage on the trail is a gem. It is an easy one mile bicycle ride to downtown Dunedin and a quick stroll to waterfront Edgewater Park to watch sunsets or see the lights of Clearwater Beach across the intracoastal waterway. Circular driveway with a carport for off street parking. The cottage is equipped with a Keurig, microwave, mini fridge, as well as beach amenities and wifi. There's a fenced back patio for you to enjoy our beautiful weather!

Nov 1 – 8

ﺩ.ﺇ405 per night

Guest favorite

Guesthouse in New Port Richey

5.0 out of 5 average rating, 103 reviews

Palm Hideaway on the Cotee River

Relax on the river at Palm Hideaway-a luxury escape to the Gateway of Tropical Florida. Our cozy guest cottage was completely renovated in 2022 & is nestled amid lush greenery on the Pithlachascotee "Cotee" River in New Port Richey. Sleep in the king size bed & have coffee or tea on your Tiki patio rain or shine. Guests have shared access to the river from the park-like backyard & can enjoy a fire in the fire pit or paddle the kayaks.

Sep 30 – Oct 7

ﺩ.ﺇ348 per night