Guesthouse vacation rentals in Florida

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Top-rated guesthouse rentals in Florida

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

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Top guest favorite

An A-frame structure features a distinct triangular design, with a white door and a small window displaying potted plants. The entrance is accented by a colorful mat, framed by lush greenery and tropical plants surrounding the area.

Guesthouse in Vieques

4.99 out of 5 average rating, 220 reviews

Artist A frame in Paradise Casa Mandala #1

Reconnect with nature at this funky unforgettable escape. This is a stand alone 10x12 A frame structure next to small main house. The restroom and shower are outdoor but private. There is hot water in shower. Large outdoor shower room with rain and regular shower heads. Ac in room is super cold. Queen bed with foam mattress Owner lives full time on property for any needs. The reviews speak for themselves about my property have an unique experience that still feels safe peaceful and comfortable.

A large window offers a view of the tropical landscape outside, featuring palm trees and colorful nearby buildings. Light curtains frame the window, allowing natural light to brighten the space. A comfortable chair is positioned nearby, enhancing the room's welcoming feel.

Guesthouse in Vieques

4.63 out of 5 average rating, 16 reviews

Esperanza Penthouse with a view (Unit 5)

Our recently renovated Penthouse is setup with 2 queen size beds, has a full kitchen combined with living/dining, & a bathroom. The side doors open to a spacious patio. Its only a 7-10 minute walk to the Malecon (the main tourist strip) in Esperanza and is close to the Green Store so you can pick up supplies. We have the fastest wifi that we could get on the island, so guests can stay connected. Tropical gardens on first floor with a mango tree. Brand-new, upgraded Air Conditioner in this unit!

Guest favorite

The exterior of the studio is highlighted by its vibrant red walls adorned with tropical motifs. A gated entrance leads to the inviting front area, while colorful umbrellas provide shade. Soft evening light casts a warm glow, enhancing the welcoming atmosphere of the property.

Guesthouse in Vieques

4.84 out of 5 average rating, 119 reviews

2 Blocks 2 Ferry - twin beds on lighthouse point

Top Ten features past guests loved; 1) no need to rent a vehicle for 1-2 day stay. Located 2 blocks from ferry and public transportation. 2) considered a safe neighborhood 3) ocean on two sides 4) you can hear the waves 5) personal greeting by experienced hostess. 6) Guestbook with money saving tips 7) luggage lockers available for early arrivals late departures 8) a walkable town beach 9) well stocked, includes beach chairs, coolers and beach towels 10) restaurants and shops a short walk

A spacious outdoor deck features comfortable seating arrangements, including a pair of wicker chairs and a small table. A hammock is suspended nearby, and a ceiling fan offers a cool breeze. Light green walls create a cheerful ambiance against the natural wood surroundings.

Guesthouse in Flamenco

4.65 out of 5 average rating, 72 reviews

Villa 3 Flamenco Beachfront Villas

Discover the hidden gem of Flamenco Beach on Culebra Island. Enjoy crystal-clear turquoise waters, protected coral reefs, and powdery white sand, perfect for snorkeling, swimming, and sunbathing. Relax in the tranquil bay, surrounded by miles of pristine shoreline and breathtaking views. Whether you're seeking adventure or relaxation, Flamenco Beach is the ultimate escape from the daily grind. Join us in paradise and discover why it's one of the Caribbean's most sought-after destinations.

Superhost

A cozy sleeping area features a spacious bed adorned with decorative pillows. A large, colorful painting hangs on the feature wall, complemented by additional artwork. Natural light illuminates the room, which includes a bedside table and a floor lamp.

Guesthouse in PR

4.86 out of 5 average rating, 285 reviews

Orita: Designer Studio with Art at Playa Negra

Artsy, rustic, jungly and secluded. Private studio suite with gorgeous black tub& rain shower, kitchen & outdoor patio on Vieques’ South side, 1.5 miles from Esperanza's restaurants and activities. Located on the lush grounds of Oro Gallery at Playa Negra's entrance, Vieques' only black sand beach. Relax in a queen size bed surrounded by art, or explore our gallery, tropical grounds, and courtyard. Cook in your small, well-appointed kitchen and enjoy the sunset views from outdoor patio.

Guest favorite

A vibrant, Spanish-style casita is surrounded by lush tropical plants and colorful flowers. The exterior is painted in warm hues, with a partially covered terrace leading to a dipping pool. Outdoor seating areas are enhanced by greenery, creating a tranquil and inviting space.

Guesthouse in Vieques

4.96 out of 5 average rating, 54 reviews

Tropical Tranquil Setting - Casita Beija Flor

There is no better place to relax and rejuvanate then in the privacy of your lovely Spanish style casita. Casita Beija Flor was designed with comfort and style in mind. The casita is situated on 4 lush private acres surrounded by vegatation and flowers. It is in the neighborhood of Destino, Vieques. The mid-island location is within easy reach of the towns of Isabel and Esperenca as well as close to the entrance of the stunning Navy beaches. Shopping and restaurants are also close by.

Superhost

A private bedroom features a spacious bed with decorative pillows and bedside lamps on each side. A modern light fixture hangs above, providing soft illumination. A small sink and mirror are positioned to one side, while patterned tiles enhance the room's charm.

Private room in Vieques

4.85 out of 5 average rating, 108 reviews

Casa San Juan Guesthouse Room D

Enjoy a stylish experience at this centrally-located place. Beautiful well maintained house in downtown Vieques. One of the best locations in Vieques. Just 8min walking from ferry terminal. Next to La Viequense Bakery and Scooters for Rent. Walk distance from Sea Glass beach, restaurants, markets and pharmacy. Private bedroom and private bathroom with shared dining, living room and spacious balcony. Room is well equipped with bath and beach towels, blankets, pillows, WiFi, Disney plus.

Guest favorite

A spacious sleeping area features a queen-size bed with a quilted gray and blue coverlet. Two bedside tables hold minimalistic lamps, and a mirror stands nearby. Natural light enters through two windows, complemented by air conditioning for optimal comfort.

Guesthouse in Luquillo

5 out of 5 average rating, 13 reviews

Walking Distance Las Pailas River - Near El Yunque

Escape to the heart of Puerto Rico’s lush countryside and immerse yourself in the rhythms of nature. Our property offers a unique opportunity to experience life as it’s truly lived in the island’s rural settings. This is more than a stay—it’s an adventure! Just a 5-minute walk away, you’ll find a private river perfect for a refreshing dip or peaceful reflection. Surround yourself with the charm of farm life, where chickens roam freely and the air carries the scent of nature’s bounty.

Top guest favorite

The villa complex is set amidst lush palm trees and manicured lawn. A shared pool is visible, surrounded by lounge chairs. Each unit features large windows and a balcony, inviting natural light. Umbrellas offer shaded seating areas for relaxation.

Guesthouse in Vieques

4.98 out of 5 average rating, 63 reviews

At The Waves - Oceanfront -Upper 2 beds/2 baths

At The Waves is a beautiful beachfront rental villa complex located in Santa Maria Playa, next to the north shore garden district of Bravos de Boston and Isabel Segunda. We have 5 units in total. This unit is the upper 2 bedrooms/2 bathrooms in Casa Las Olas. The master bedroom has a King size bed and an on suite bathroom with a spacious closet. It has a wrap around porch ocean front with views of the island of Culebra and El Yunque on the main island of Puerto Rico.

Superhost

A modest concrete building is framed by lush tropical foliage. Potted plants adorn the exterior, and textured gravel leads to a small step area. Light and shadow play across the surface, with window shutters providing ventilation and aesthetic detail.

Guesthouse in Vieques

4.77 out of 5 average rating, 64 reviews

Magnolia Esperanza Cottage

As seen on HGTV! Enjoy life as a local at Casita Magnolia. Let our cozy studio be your home base for experiencing the delights that Vieques has to offer - secluded beaches, Bio Bay, snorkeling with sea turtles. Start with your morning coffee in the shady, secluded gazebo and plan your adventures for the day. Meals can be prepared in the full kitchen, or savor local foods nearby. Enjoy the sights and sounds of this beautiful quirky small island.

The exterior of a casita is presented, featuring a brick archway leading to a white door. An air conditioning unit is visible on the orange-painted wall. A landscaped area with various plants and a stone seating area can be seen in the yard.

Guesthouse in Vieques

4.8 out of 5 average rating, 5 reviews

Orchindeas

A house without luxuries, but clean and safe, half a block from all the shops and restaurants in Esperanza. 1 large bedroom with a queen size bed and 2 single bunk beds and air conditioning. Here are the pros: - Walking distance to everything you need, supermarkets, tours of the bioluminescent bay, Playa Sun Bay, shops and restaurants of the Malecón. -property safe -private house and patio with hammock

Guest favorite

The bedroom features a spacious bed with decorative pillows, complemented by a wooden headboard. A bedside lamp casts a warm glow, while patterned curtains frame the windows. Light-colored walls and tiled flooring enhance the room's inviting ambiance.

Guesthouse in Vieques

4.83 out of 5 average rating, 24 reviews

Casa Iguana

A peaceful 1-bedroom studio surrounded by the beautiful island scenery of Vieques, Puerto Rico. With just a 15-minute drive to the beautiful white sandy beaches where you can swim and enjoy snorkeling with the family. Located centrally Villa Borinquen, 10-minute drive to Malecon, where you can enjoy the local restaurants while enjoying the view of the Caribbean Ocean.