50 Best Vacation Rentals in Osa Peninsula - Holiday Lettings - Cabins

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Drake Bay
33 properties
Puerto Jimenez
27 properties
Cabo Matapalo
16 properties

Osa Peninsula

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129 Vacation rentals

(16) Excellent 

19

Vacation bungalow rental

Osa Peninsula / Cabo Matapalo

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Have your own private off-the-grid cabin in the jungle of Costa Rica's Osa Peninsula, and just steps from a secluded beach. You'll see monkeys off your front porch, pick your own fresh mangoes off the tree in your front yard, and go for a surf at an excellent point brea …see more

from $85 / night

$500 - $920 / week

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from $85 / night

(8) Excellent 

21

Vacation bungalow rental

Osa Peninsula / Cabo Matapalo

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Have your own private off-the-grid cabin in the jungle of Costa Rica's Osa Peninsula, and just steps from a secluded beach. You'll see monkeys off your front porch, pick your own fresh mangoes off the tree in your front yard, and go for a surf at an excellent point brea …see more

from $85 / night

$500 / week

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from $85 / night

14

Vacation home rental

Osa Peninsula / Puerto Jimenez

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Private garden
This charming open air beach house is only steps from the ocean. Watch the sunrise from the comfort of your bed and listen to the Scarlet Macaws as they serenade you from their favorite tree in the area, right next to the house!! Nestled in the curve of a secluded bay …see more

from $120 / night

$725 - $1,145 / week

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from $120 / night

5

Vacation b&b in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
Bed and Breakfast in charming house .Climatisation and refrigerator in each room. Near the center of the village, the beach (5 minutes walk) and the entrance to the Corcovado Park. Private garden or rub macaws, toucans, squirrels and many birds with a sitting area and h …see more

from $45 / night

$315 / week

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from $45 / night

9

Vacation home in Drake Bay

Osa Peninsula / Drake Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Air conditioning
  • Private garden
We are locate in Drake Bay ., north side from Corcovado National Park in la Peninsula de Osa Puntarena CostaRica. casita cecropia is locate 700 m eter from the beach or 400 meter from Drake store ., we are local family that live in Drake Bay area and now …see more

Pricing unknown

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Pricing unknown

17

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Jungua (recently completed) was built by a master timber framer and everything about it screams QUALITY. It is sustainably built and has an extremely low impact on the environment. The house is exclusively solar powered yet features many amenities one would expec …see more

from $328 / night

$2,300 / week

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from $328 / night

(2) Excellent 

14

Vacation home in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
Casa Troya is an open air, bamboo house. The design reflects the typical home design of the Osa Peninsula with its half-height walls and natural, local building materials. It has a fully equipped kitchen and bathroom downstairs, and a loft partitioned into two bedrooms …see more

from $100 / night

$650 - $1,075 / week

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from $100 / night

(19) Excellent 

Certificate of Excellence

32

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
Located in an area of Costa Rica known world wide for the diversity of it's flora and fauna, The Osa Penninsula. This wonderfully ecologically balanced area is incredibly essentially free of Mosquitos given the number of Bats and Birds that are the Mosquito's predator …see more

Certificate of Excellence

from $125 / night

$700 - $1,400 / week

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from $125 / night

(2) Very Good 

24

Golfito Vacation home rental

Osa Peninsula / Golfito

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Beautiful Home with two room available with bath and shower each one. All utilities include!! The owner lives on main floor, recently built and luxiourious.. Located in Golfito adjacent to four star hotel with fine dining and bar just steps away. Neighborhood …see more

from $160 / night

$850 / week

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Responds fast!
avg. 3 hours 26 minutes

from $160 / night

(15) Excellent 

17

Vacation home in Drake Bay

Osa Peninsula / Drake Bay

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
This newly built small house is fully self contained with kitchen, bedroom, 3 piece bathroom, plumbed hot water to all faucets, outside roofed porch with hammocks, handmade wooden bench-swing, patio table and chairs. It is built using locally cultivated, sustainable ha …see more

from $135 / night

$945 / week

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from $135 / night

13

Vacation home in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Ask about pets
Casa Rio Sombrero is custom-finished with fine hardwoods, has an open floor plan, and a beautiful thatched roof. The upstairs has two bedrooms containing king-sized, netted beds. A twin bed can be added to one of these rooms for extra sleeping space. Downstairs, there …see more

from $150 / night

$1,000 - $1,425 / week

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from $150 / night

(7) Excellent 

20

Vacation home with swimming pool in Golfito

Osa Peninsula / Golfito

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Golfito is located in the historic "Zona Americana" section of Golfito. The house was originally built by United Fruit Company as part of the housing provided to their executive management. This gated home sits on a one acre lot and includes a pool, rancho and beau …see more

from $375 / night

$2,625 / week

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Responds fast!
avg. 2 hours 7 minutes

from $375 / night

(2) Very Good 

24

Home accommodation in Drake Bay

Osa Peninsula / Drake Bay

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
This is your chance to completely escape the monotonous grind of everyday life and rejuvenate your body and mind with a healthy dose of natural beauty, active adventure, rustic luxury, and cultural authenticity. All five senses will be on full alert here…each one contri …see more

from $150 / night

$1,000 - $1,630 / week

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from $150 / night

11

Drake Bay Vacation home rental

Osa Peninsula / Drake Bay

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
SuChante is a fully equipped two story house in the rainforest. The Kitchen and Lounge with Sofa, Library and Board Games are located downstairs. As well as the outdoor dining area.An anexion with a private room and own bathroom is located downstairs too. Upstairs there …see more

from $80 / night

$560 / week

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from $80 / night

13

Vacation lodge in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Pet friendly
Descanso La Pizota is a remote hostel located in a forested area bordering Corcavado National Park. Through our breath-taking trails we offer you the chance to submerse yourself in nature experiencing a tranquil, beautiful slice of reality. THE AREA The Osa Peninsula …see more

from $10 / night

$70 / week

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from $10 / night

(5) Excellent 

24

Vacation log cabin rental

Osa Peninsula / Puerto Jimenez

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Casita Tranquila is located in a tropical setting on a secluded beach on the Osa Peninsula South of Puerto Jimenez on the way to Corcovado National Park. There is room for up to 5 people. The house features two bedrooms, a kitchen, living room, porch/deck, and private …see more

from $99 / night

$693 - $1,218 / week

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Responds fast!
avg. 3 hours 39 minutes

from $99 / night

(14) Excellent 

28

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Wake to the sound of howler monkeys, toucans, scarlet macaws & the running river below! Sip your coffee whilst watching giant blue morphs dance in the early morning sunlight! Smell the fragrant frangipani & ylang ylang! Experience the intense, inspiring majesty & the Pu …see more

from $140 / night

$840 - $1,190 / week

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from $140 / night

(2) Excellent 

32

Vacation home with shared pool in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
Beautiful "Open Air" two-story safari home with 3 private bedrooms that sleep 6. There are 2 hanging Hammocks in main central room for 2 additional guests if needed. Property is privately situated at the end of Matapalo Beach rd. on a pristine secluded beach surrounded …see more

from $149 / night

$1,043 / week

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from $149 / night

(2) Excellent 

43

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Car not necessary
Visitors repeatedly say that Casa Sonrisa and our other bamboo houses are exceptional, and have made it a Travelers Choice Winner on TripAdvisor for four years. This year it was among TripAdvisor’s top hotels for families in all Costa Rica and Central America. Located o …see more

from $195 / night

$1,330 - $1,795 / week

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from $195 / night

(1) Excellent 

15

Cabo Matapalo Vacation lodge rental

Osa Peninsula / Cabo Matapalo

8 23 1 night min

  • 8 bedrooms
  • Sleeps 23
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Ojo del Mar ("eye of the sea"), is a small, eco friendly secluded retreat nestled between the pristine beaches and the tropical rainforest in the wilds of Costa Rica's Osa Peninsula. As National Geographic says, the Osa is the "Last Great Peninsula," still untouc …see more

from $130 / night

$780 / week

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Responds fast!
avg. 2 hours 10 minutes

from $130 / night

11

Drake Bay Vacation bungalow rental

Osa Peninsula / Drake Bay

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Two story loft style house. Perched on a hill above beautiful Playa San Josecito. 5 minute walk to the beach, 1 1/2 hour hike to Corcovado Park, the jewel of the Osa Peninsula! Gorgeous sunsets and view of Cano Island right from the balcony! Totally private …see more

from $225 / night

$1,575 / week

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avg. 3 hours 10 minutes

from $225 / night

(14) Excellent 

19

Puerto Jimenez Vacation home rental

Osa Peninsula / Puerto Jimenez

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Ask about pets
A towering three-story treehouse set amid the jungle canopy, Punta Jaguar is the perfect base for your adventures on Costa Rica’s Osa Peninsula. Built with unique, breathtaking views of the ocean and jungle, Punta Jaguar is alive with the myriad species of birds and ani …see more

from $300 / night

$2,450 / week

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from $300 / night

(1) Excellent 

14

Vacation home rental

Osa Peninsula / Puerto Jimenez

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Child friendly
Simple yet comfortable tropical screened home with an open style floor plan inside, large patio with hammocks outside. 110 yds from the pristine Golfo Dulce, ocean view thru trees, this rental offers access to jungle and sea adventures. …see more

from $99 / night

$693 / week

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from $99 / night

(2) Excellent 

12

Vacation home with swimming pool in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Private garden
Osa Stardust is a complete home in the hills overlooking the waters of the Golfo Dulce and the jungle canopy of the Osa Peninsula. The house has the privacy of a jungle retreat with a wraparound deck for sunning and bird watching. The sound of the surf on nearby b …see more

from $68 / night

$476 / week

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Responds fast!
avg. 3 hours 28 minutes

from $68 / night

72

Vacation cottage in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.001 mi
  • Child friendly
When was the last time you thought that Life was way too busy? Wouldn't it be nice to take a Time-Out from the "fast-track" and experience an alternative. Something Basic, Simple yet Elegant and which offers complete Freedom to be who you really are or maybe even who yo …see more

from $79 / night

$499 / week

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Responds fast!
avg. 1 hour 33 minutes

from $79 / night

7

Vacation home rental

Osa Peninsula / Puerto Jimenez

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Fishack is a harborfront residential complex that includes three separate lodging options available either separately for small parties or together for groups. All are available for short-mid term rentals. The three-story home is situated on the edge of the Puert …see more

from $140 / night

$900 - $1,250 / week

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from $140 / night

1

Vacation hotel apartment with shared pool in Drake Bay

Osa Peninsula / Drake Bay

7 24 1 night min

  • 7 bedrooms
  • Sleeps 24
  • 1 night min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Hotel Treasure Mountain Sir, back in the Treasury of Sir Francis Drake, because of the natural wealth of primary forest, flora and fauna. Located 5 km from the second largest Biological Station of Corcovado National Park: Plans. The Hotel is immersed between the primary …see more

from $80 / night

$355 / week

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from $80 / night

(1) Excellent 

25

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Private garden
5-star ranking recipient of 8 Traveler's Choice Awards and 9 Excellence Awards. Recommended by Lonely Planet. Casa Bambu is one of four bamboo beach houses on our six acre resort property. (If Casa Bambu is reserved for the dates you want, see the listing for Casa Linda …see more

from $145 / night

$985 - $1,795 / week

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from $145 / night

28

Vacation guest house in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
We are located just minutes from beaches and reserv corcobado and 10 minutosde Highway 245 shops and front and 10 minutes from the local airport, pick up our guests, also we contacted them for different tours.paseo boat in the Golfo Dulce spotting whales and delfines.ca …see more

from $46 / night

$322 - $952 / week

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from $46 / night

11

Vacation home in Drake Bay

Osa Peninsula / Drake Bay

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
This is perfect with sea view in Drake Bay for those who love the ocean view and tranquility. The house is 80 square meters and has a deck of 6×8 meters so you have enough space for your convenience. Home Features Overlooking the Pacific Ocean 5 single beds Kitchen Fu …see more

from $260 / night

$1,820 / week

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Responds fast!
avg. 3 hours 23 minutes

from $260 / night

42

Puerto Jimenez Vacation home rental

Osa Peninsula / Puerto Jimenez

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
The Toucan Hut is the junior suite at Casa Manglar Guest House. It's aptly named because many days of the year one may view Toucans from the windows of the room. Double bed with A/C, En-Suite Bath and full walk-in Closet and Wifi and access to 2 swimming pools on the pr …see more

from $79 / night

$499 / week

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Responds fast!
avg. 1 hour 33 minutes

from $79 / night

(12) Very Good 

27

Vacation home accommodation

Osa Peninsula / Drake Bay

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.001 mi
  • Child friendly
This AIR CONDITIONED home is a 2 bedroom house with magnificent hilltop views of Drake Bay. This home boasts of the best view of Drake Bay of all the homes along the beach. Private and central to all necessary amenities. Full kitchen, and an amazing backyard patio with …see more

from $135 / night

$900 - $1,425 / week

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from $135 / night

33

Vacation home in Cabo Matapalo

Osa Peninsula / Cabo Matapalo

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.08 mi
  • Child friendly
Visitors repeatedly say that Casa Pina is exceptional. So take a walk on the wild side! This off-grid Costa Rica beach rental offers nature lovers, surfers and fishermen an ideal vacation. It sits on four acres of beautiful beachfront and world-class SUP surfer's dream …see more

from $195 / night

$1,345 - $1,795 / week

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from $195 / night

5

Drake Bay Vacation villa rental

Osa Peninsula / Drake Bay

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Welcome to Villa Cecropia. We are running a newly opened hotel in a proximity of both beach of Drake and primary forest. Being located within walking distance to all that the town has to offer (shops, restaurants and more) and at the same time tranquility of our garden …see more

from $145 / night

$1,250 - $2,020 / week

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from $145 / night

(1) Excellent 

26

Home rental in Puerto Jimenez with indoor pool

Osa Peninsula / Puerto Jimenez

6 9 4 nights min

  • 6 bedrooms
  • Sleeps 9
  • 4 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Osa Springs- It’s almost like having a resort all to yourselves since this is a private reserve. No need to decide if you want a Costa Rica beach house rental or rain forest rental - here at Osa Springs Luxury Resort -You get both! Complete and total privacy for rental …see more

from $110 / night

$770 / week

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from $110 / night

(15) Excellent 

51

Vacation home in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Casa Bella de Osa has just finished major renovation, (more photos to come) This newly renovated, large, three bedroom, 2 bathroom house with high ceilings and many lounging areas, makes for the perfect holiday beach rental house. Within 2 minutes walk from the house y …see more

from $200 / night

$1,400 - $2,100 / week

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Responds fast!
avg. 2 hours 10 minutes

from $200 / night

(1) Very Good 

16

Home rental in Puerto Jimenez with shared pool

Osa Peninsula / Puerto Jimenez

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Playa Sombrero has an open construction style that allows for a steady ocean breeze throughout the living space and provides both ocean and lush mountain views. Upstairs has a large floor plan with a beautiful hardwood floor and a thatched-roof ceiling. This room …see more

from $180 / night

$1,200 - $1,750 / week

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from $180 / night

28

Vacation guest house in Puerto Jimenez

Osa Peninsula / Puerto Jimenez

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
surrounded booths fruit and timber trees, green areas, room with country kitchen, barbecue and Trapiche de cana artisanal sugar, they can enjoy the fruits of the season as pipa (coconut, water apple, cashews, nances, we are 10 of the beach, rivers and reserve corcobado, …see more

from $46 / night

$322 / week

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from $46 / night

(3) Excellent 

55

Puerto Jimenez Vacation villa rental

Osa Peninsula / Puerto Jimenez

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Casa Manglar is a beautiful tropical home with 4 bedrooms each with A/C. It offers both a master and junior suite each with cable TV, walk in closets and private bathrooms. These suites are gems in Puerto Jimenez. Casa Manglar is the old family home of the owners of the …see more

from $249 / night

$1,499 / week

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Responds fast!
avg. 1 hour 33 minutes

from $249 / night

(1) Excellent 

13

Vacation hotel apartment rental

Osa Peninsula / Golfito

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
Located on the calm, turquoise waters of the Golfo Dulce in Costa Rica. We may be remote but you don't have to suffer. The beach house has solar electric, ceiling fans, full screening and hot water shower. Just steps from the beach, the two-story beach house is construc …see more

from $260 / night

$1,820 - $7,280 / week

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from $260 / night